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CARIBBEAN YACHT CHARTERS

Caribbean yacht charters, is synonym to tropical paradise and an excellent sailing destination. White sandy beaches, clear waters and palm trees make Caribbean bareboat charter an unforgettable sailing experience. Islands surrounded by the Atlantic Ocean and Caribbean sea, provide numerous destinations.

Rent a Boat in Caribbean: 1297 Available

Robertson caine 51 pc power boat charter (2015).

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Dufour 412 GL sailboat charter (2018)

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Caribbean Yacht Charter Reviews with 12knots

Matthew Gunnison

“Thanks for helping to coordinate!”

It was terrific, thanks. Sail Marine is a great outfit. Thanks for helping to coordinate! Best, Matt

YACHT CHARTERS

Flori Grottoli

“Spanish Virgin Islands are stunning / March 2019 / Puerto Rico / Dufour 412”

The experience was beautiful and the Spanish Virgin Islands are stunning! Even though we started off with a few setbacks (had to switch boats because of technical issues), the marina made good and was very accommodating....they did the very best they…

Greg Spalek

United States

“Relied on 12knots' team for 3 of my voyages”

I've relied on this 12knots' team for 3 of my voyages (Mexico, Tahiti and Croatia). Their website is very good to browse and they stand behind their portal. They are always fast to respond to questions/concerns. It is always a pleasure to deal with J…

Ven Dobrinov

“Everything was perfect!”

Dear Grigory, Everything was perfect! Thank you :) Please see the attached photo.

“Everyone had a very nice time”

Thank you - it was a really nice experience. You were very helpful during our departure and arrival. The boat was amazing, well outfitted, and everyone had a very nice time. I'll be sure to send you some photos over the weekend. We also have some dro…

“Everything was fine”

Every time I ordered a boat using 12 knots everything was fine. Every question was answered, support provided.

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Sailing Around Windward and Leeward Islands of the Caribbean

The  Caribbean covers a huge region of widely spread islands 2,000 miles (3,218 km) long.

The larger ones have become sovereign countries with broad range of amenities for sailors, while the smaller ones still preserve its untouched rural charm and tranquility.

From the western tip of Cuba to the Leewards in the east, then south to the top of South America and along Venezuela’s north coast – this chain of islands has created a hook-like shape around the Caribbean Sea. Location like this is always an enticing bait for sailing - perfect climate and  array of diverse cultures, customs, cuisines and experiences, water sports and an unlimited number of other attractions.

Planning sailing vacations in Caribbean, you may wish to consider these groupings of the islands as points of your itinerary, as they contain many popular cruising areas and harbor stops. There is no doubt that in the scope of Caribbean bareboat or skippered yacht charters  both groups have their charms and countless reasons to explore, which definitely makes it a great sailing destination.

Caribbean yacht rentals

12 Knots offers eleven yacht charter bases in the Caribbean region, each with unique individual character, providing sailing experience for everyone, from a novice to an experienced sailor. This region comprises more than 700 hundred islands and islets, so you can choose Caribbean sailing vacations with shot and easy hops or more challenging passages.

Taking Caribbean sailing vacations, you will find warm and steady trade winds in picturesque surroundings; discover plenty of great bars and authentic cuisine!

It’s up to you, choosing between the Leeward Caribbean islands with short and easy hops with line-of-sight sailing and the Windward with more challenging open water passages. Wherever you go, you will return home relaxed, refreshed and ready to start planning your next Caribbean sailing adventure.

The Windward islands

Windward Islands located at the southern end of the Caribbean island chain and stretch for over 300 miles to the south-eastern end of the Caribbean Sea. The Windward Islands are simply called so due to their position as they are exposed to the northeast trade winds. For experienced sailors, it can be right choice to sail among the four main islands: Martinique, St. Lucia, St. Vincent and Grenada. They lay far apart each other allowing open ocean sailing and while steady easterly trade winds, make passages north or south easy. With constant 12 to 25 knots wind, Caribbean sailing is among best in the world. Night anchorages in peaceful and protected areas give sailors freedom to explore and soak up British and French island culture. The islands of St. Lucia, St. Vincent and Grenada  were British colonies until they gained independence during the 1970s. Martinique is still an overseas department of France.

The climate of the Windward Islands is definitely a marine one.

When tropical heat reaches its peak, steady trade winds and daily sea breezes come to rescue.

Typically, dry and wet seasons go hand in hand here. Although the priority of more rainfalls is given to the eastern side of the islands mainly due to the prevailing north-east trade winds there.

The islands east of Puerto Rico were called “Windward Islands” by the Spanish, while the islands south of Puerto Rico were named as “Leewards “. And Dominica positions itself right on the border line between the Windward and the Leeward Islands.

Long time ago some of the islands used to be French colonies, subsequently gained its name as The French Antilles.

The population of the Windward Islands is mostly of African origin, with some exceptions of Chinese and Caucasians. The present day Windward Islands will welcome tourists with upscale resorts, stunning beaches and pleasant sunny weather.

After cruising through the Windward Islands, you may wish to set sails to the Leeward Islands.

The Leeward islands

The Leeward islands are located on the eastern edge of the Caribbean Sea and form the northeastern boundary between Caribbean and Atlantic Ocean, extending from Puerto Rico to the Windward Islands, forming part of the Lesser Antilles chain.

Although 700 miles long stretch of these magnificent isles mostly constitute the whole body of the Leewards, it provides the abundance of enjoyment: quaint fishing spots, ancient ruins and delicious authentic cuisine.

Blessed with balmy temperatures all around the year, The Leeward Islands are called leeward because they're away from the wind or downwind (in the "lee"). Leeward group of Caribbean islands includes: the U.S. Virgin Islands, the British Virgin Islands, Anguilla, Saint Martin, Saint-Barthelemy, Saba, Sint Eustatius, Saint Kitts, Nevis, Barbuda, Antiqua, Redonda, Montserrat and Guadeloupe.

One of two "sister islands", St Kitts and Nevis, provides a brilliant Caribbean experience, from their picture-perfect beaches and volcanic mountains to friendly locals and layers of history to explore. For the water sport lovers, there are numerous aquatic activities that include fishing, diving, windsurfing and surfing.

St.Kitts and Nevis

Switch from sailing to inland for a change and St.Kitts and Nevis will deliver the most exceptional hiking in the Caribbean. The dormant volcano of Mount Liamuiga is considered to be the toughest to climb. And with the experienced guide you may even try to descend in its crater!

The unspoiled landscape of dry littoral forest and rainforest will present memorable show of fauna and flora. Many plants are of culinary and medical use, and some even used in black magic, as informative guides would point out its botanical value.

The wild life-lovers will not be disappointed with variety of different types of exotic animals.

Actually, the Great Salt Pond has become famous for its largest habitat of green velvet monkeys.

St. Kitts and Nevis will keep you captivated with majestic view of huge conical shells, remains of old sugar mills, along with some other plantation ruins, built in the 18 th century.

Back to water activities, and tourists will be pleased with what these two island can offer: deep-water fishing, snorkeling, scuba diving and more.

Then in order to satisfy your growing appetite visit two popular restaurants: Carambola and the Shipwreck Bar and Grill to enjoy its delicious local meals.

A yacht charter in the Caribbean Leeward Islands offers sailors an unrivalled remarkable experience. Enjoy tropical landscapes, pristine palm-lined beaches and azure waters — all the joys of marine life.

Sailing over the Leeward Islands may have all the pleasures to offer: the Tropical rainforests, glittering coral reefs, and luxury sand beaches. That’s probably why most of the known tourist resorts on these islands play a critical role in their economy, as do banking and fishing. Many of them also rely on their status as a tax haven to promote offshore financial services as a source of government revenue. But there is much more to discover in the Leeward Islands. These Caribbean islands provide great variety of yachts for charter and pleasant sailing vacations. Most of the Leeward Islands are located close to each other with moderate winds from 10 to 15 knots and rather low wavers. BVI is the most popular area for Caribbean charters either bareboat or luxury crewed vacations. This is the right place for the novice sailor’s easy passages in line-of-sight sailing.

The climate of the Caribbean Leeward Islands can be described as tropical, but much drier than in Windward Islands. Though the climate does vary from island to island and can even be different in different parts of the same island. Rainfall increases with elevation and in more southerly latitudes. In some cases trade winds look like refreshing tonic to the tropical heat. There is minor seasonal variation, although the second half of the year, the wet season, is slightly warmer and rainier. The best time for sailing in the Caribbean may be the first half of the year. At this time the temperatures usually range between 81°F (27°C) and 95°F(35°C). Annual rainfall averages about 40 to 50 inches (1016 to 1270 mm). Keep in mind, that nearly every island had been severely damaged by hurricane activity in its recent history.

English is the most widespread language all around the islands, plus many of the people speak French and Dutch on the St Martin Island. Both English-based and French-based Creole are also spoken. The prevailing currency is The East Caribbean dollar. But St Martin is odd man out again, circulating the Netherlands Antilles guilder in the Dutch area and the Euro in the French region. Nevertheless, the US dollar is widely accepted throughout the islands.

If you eager to take part in sporting activities, then you may be pleased to know that cricket is widely played and followed in the former British territories. Besides, as in the rest of the Caribbean, music is also always a big part of local life. Enjoy the magical sounds of calypso, soca, steelpan, reggae, salsa and jazz — all of the mentioned has their adherents.

During your Caribbean yacht charter, you may wish to participate in some major holiday celebrations, including the St Kitts Christmas, New Year carnaval, the annual music festival, as well as Anguilla’s Emancipation Day and Culturama festival on August 1st.

The culture of the Leeward Islands is varied by different influences, including French, Dutch and West Indian. Due to that sailing around the Leeward Islands provides a wonderful choice of cuisine and some great restaurants to satisfy your affection for the finest dishes. By the way, the island of Anguilla offers true gastronomic feasts. When sailing in the Caribbean Leeward Islands, be sure to try freshly caught lobsters with a glass of wine.

Sailing the Caribbean With 12 Knots

So, while planning a Caribbean charter it is highly recommended to decide on how many islands you would like to visit in a given time frame. Research Caribbean boat rentals and determine which island you would like to have as a starting base. Then you can plan an itinerary for the week or ten days, taking into consideration distances between the islands and activities you would like to have, like island tracking, scuba diving, snorkeling, volcano hiking, or even shopping.

12 Knots team will give you plenty of useful information not only on the bareboat charter in Caribbean, but also itineraries, places of interest and peculiarities of each island.

Taking a yacht charter in the Caribbean is just a perfect combination of sailing and relaxation, authentic culture and a range of water sport activities. In a few words, this area may always offer something for everyone in these amazing islands’ surrounding.

Frequently Asked Questions about yachting in Caribbean

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Color and Contrast: the Complete Sailboat Vacation

Simply the perfect place to take a bareboat or skippered sailing holiday. Such a diverse collection of islands dotting the clear blue sea, each with its own unique appeal. Local cultures that fascinate and entertain, offering a welcome that keeps charterers returning to these waters year after year. With its 7,000 Islands and 28 Island nations, reliable trade winds and long sailing season, the Caribbean is a region that offers an endless amount of holiday enjoyment.

At Sail Connections, we work with all the best charter operators in the Caribbean, sorting through all the available boats and presenting all the best options to suit your vacation plans. Some of our operators offer extra services that are unique to their destinations. We personalize your proposal and give you the benefit of our knowledge and local contacts, to deliver a fabulous sailing holiday wherever there's a boat to charter in the Caribbean. 

Charter Sailing in the Caribbean

The Caribbean's numerous islands give you so many fabulous places to explore, so many diverse cultures to experience, that the permutations for planning a sailing charter are simply too numerous to list. The sailing distances between territories can be very short, and there are countless yacht charter bases scattered across the region. That opens the door to all manner of opportunities – from a seven-day sail around one distinct island nation to a multi-week one-way charter that takes in a wide variety of cultures and geographical features.

The Caribbean yacht charter season is busy from November through July. The peak season is mid-December to March, when winter escapees from North America and Europe arrive in their greatest numbers.

The hurricane season arrives late July and can last until early October, although storms here are rare and tend to deflect northwards towards the USA rather than hit the Caribbean. These months have their advantages in that they are the least costly for chartering, particularly in the British Virgin Islands. At that time of year it is in fact more likely to encounter light winds than it is storms.

As with many yacht charter locations, the shoulder season can be the best time to charter a yacht. In the Carribean that's from April to July. There are less shore-based visitors then, yet you can expect settled and sunny weather with warm, steady breezes prevailing.

We have access to over 30 charter bases in the region, from where you can take a sailboat vacation like no other. We select from the best boats available and guide you into the ideal sailing adventure that matches your interests and level of experience. The sailing options here are just about endless. Hopefully these pages will help you on your way to your much-anticipated Caribbean sailing holiday.

Regional Map of the Main Charter Sailing Areas

A One-way Cruise: Martinique to Grenada

There are quite simply countless itinerary options for sailing the caribbean. for many charterers a downwind cruise offers the crew conditions for maximum enjoyment. so here's a sample north to south course plan that gives you the prevailing breeze abaft. .

Martinique waterfront

Waterfront at Fort de France, Martinique's largest town

Sailing from Martinique to Grenanda you can expect winds primarily from the northeast, especially around peak season either side of Christmas. Sailing this course involves short stretches of open water, with a stiff and steady breeze on your aft quarter. That makes for quick passages with most enjoyable sailing to a choice of Islands, whether it be for a lunch stop and a snorkel, or an overnight stay.

The eastern Caribbean islands that form a distinctive arc on the map are collectively the Lesser Antilles, a mixture of soverign states and territories governed by various powers. A trip along some of this chain exposes the voyager to a wide variety of cultures and customs in places that all sit in the idyllic picture-postcard surroundings of the movies and travel brochures. 

Starting in Martinique and sailing south, you are exploring the Windward Island group of the Antilles.

Tobago-cays

Wildlife viewing at its finest in the Tobago Cays

Like most of this group, Martinique was orginally colonised by France, and French flair is still in evidence there today. Martinique offers excellent on-shore facilities for the visitor, and is a popular base for boat charters. The island is mountainous, but with plenty of white sandy beaches to enjoy, especially in the south.

The next island is St Lucia. It's some 30 nautical miles to Rodney Bay on St Lucia's northwest, so to get there requires an early start. There are several top spots to visit down the island's sheltered western coast. Take time out to investigate Les Deux Pitons.

Another long but relaxing sail to St Vincent and the Grenadines, so-named because of their joint French and British colonial history. St Vincent has its Blue Lagoon that you'll probably overnight in, while the Grenadines island group, some of which confusingly belong to Grenada, provide numerous anchoring options.

Grenadines

Happy charterers enjoying their time ashore in the Grenadines

The Grenadines stretch all the way to Grenada, your final port of call, making this part of the voyage very convenient for a leisurely sail. Call in at one of the uninhabited Tobago cays for a real taste of desert island living, if only for a few hours.

Once offshore Carriacou you are in Grenadan territory. Grenada, like St Lucia & St Vincent and the Grenadines, is now an independent member of the British Commonwealth, but with historical French influence. This is the 'Island of Spice' where nutmeg and mace production are important to the economy. As is tourism, and there is plenty to entertain you before concluding your vacation and departing these fabulous sailing waters.

Once you have experienced all the pleasures of sailing the Caribbean, chances are you'll be back one day for more.

The Best Caribbean Charter Sailing Destinations

Bahamas

British Virgin Islands

US Virgin Islands

US Virgin Islands

Puerto Rico & Spanish Virgin islands

Puerto Rico & Spanish Virgin islands

Cayman Islands

Cayman Islands

St Martin, St Barts, Anguilla, St Kitts & Nevis

St Martin, St Barts, Anguilla, St Kitts & Nevis

Antigua & Barbuda

Antigua & Barbuda

Guadaloupe

Martinique, St Lucia & The Grenadines

Grenada

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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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Caribbean Splurge: A Sailboat of Your Own (Well, Sort of)

What you need to know to charter a sailboat in the Caribbean, from costs and type of vessel to timing and itinerary.

A sailboat, sails furled, is anchored in the clear, aqua waters of the Caribbean. Smaller boats, including a kayak, surround the double-hulled boat, and in the distance are mountainous islands beneath a blue sky strewed with puffy clouds.

By Christopher Hall

Last April, Chris Kotchick, a Scranton, Pa., oral surgeon, and his family spent a week on a chartered catamaran in the calm, clear waters off the British Virgin Islands. A crew of two — part of the deal — ran the show.

Until then, Dr. Kotchick said, the sum total of his nautical experience had been riding ferries. But his search for a vacation that would appeal to his wife, Bridget, a high school biology teacher, and their two teenage children led him to a 50-foot-long boat, which they used as a base for swimming, snorkeling, wake-boarding and scuba diving as they sailed from island to island. They slept onboard and mostly skipped onshore restaurants, wowed by the crew-cooked meals that could be shared with their daughter, who has celiac disease.

As to cost, the trip was, for them, an affordable splurge — just over $20,000. “It wasn’t that much more than the blowout Disney World vacation we took when the kids were younger,” said Dr. Kotchick, adding that two others had joined the family on that trip. “And it was a lot more fun.”

Though the image of yachting in the Caribbean skews more oligarch than average Joe, the Kotchicks are far closer to typical crewed yacht clients than the likes of Jeff Bezos aboard his schooner, which is more than 400 feet long and cost a reported $500 million. After a pandemic lull, more people of comfortable, but not necessarily extraordinary, means are booking these trips, and the trend is edging higher. According to an April 2023 report from Fortune Business Insights, the global charter yacht market — including both crewed and sail-it-yourself, or bareboat, charters — is expected to grow 5.5 percent by 2030, with yachts under 40 meters (about 131 feet) accounting for the largest share.

Because the cost includes a crew, passengers don’t need specialized maritime knowledge, which means the trips draw a variety of travelers.

“Some of our clients are more into active sports, and others prefer relaxing with a book or checking out onshore restaurants, bars and resorts,” said Carlos Andrade, a captain who, with his wife, first mate and chef, Maribel Ramirez, has run trips in the Caribbean and elsewhere for more than 30 years, most recently aboard their 44-foot catamaran, Alizé . “But all of them love the outdoors and simply being close to water.”

For Steve McCrea, a broker at the yacht charter agency Ed Hamilton & Co. , the most common question from prospective clients is whether their kids will get bored on a boat. “I tell them that, yes, it’s a sailing vacation,” said Mr. McCrea, who has been booking crewed Caribbean trips for 26 years, “but, in fact, it’s more like a floating resort on the move, with loads of activities, sports gear and great beaches where you can spend the day.”

Jim Grant, a broker at Carefree Yacht Charters , said passengers do not need to meet any specific benchmark of health or physical fitness. “If you can comfortably navigate jet travel to get to the boat,” said Mr. Grant, “you’ll be fine on board.”

The nitty-gritty: boats and cost

In the Caribbean, crewed catamaran sailboats with their double hulls far outpace power boats and single-hull sailboats as the vessel of choice. “They’re more stable on the water, which is great for people without a lot of sailing experience,” said Mr. Andrade, the yacht skipper. “And in terms of onboard space, they can’t be beat when you compare different kinds of boats of similar length.”

A boat’s size and age largely determine the cost of a charter, with price bumps occurring during the holidays. For a weeklong trip for six passengers aboard an older catamaran with three en-suite guest cabins and a crew of two in its own cabin, the per-person fee starts around $2,500 for a vessel under 50 feet. That gradually rises to $5,000 and up for a somewhat larger and newer boat and zooms ever higher as size and newness increase. A week aboard a two-year-old, 80-foot catamaran with four en-suite cabins and a crew of four, for example, can easily approach $20,000 per person. In the Caribbean, the charter fee is usually inclusive, meaning that meals, alcohol and fuel are folded into the cost. Only the customary 15 to 20 percent gratuity is extra.

Crewed charter trips can fill up fast. “For the best selection, you should think about booking at least six months in advance for popular times like spring break, Easter and Thanksgiving,” said Els Kraakman, a British Virgin Islands-based broker with Waypoints Yacht Charters . “For Christmas and New Years, it can be more like a year.”

Unless you’re chartering a megayacht with its own gym and sauna, amenities are fairly uniform. Even on moderately sized vessels, they usually include Wi-Fi, air-conditioning, music systems, swimming platforms, on-deck showers (in addition to those in cabin heads), motorized dinghies for water sports and transport to shore, and an arsenal of sporting equipment like kayaks, stand-up paddle boards, and gear for snorkeling and fishing.

Alfresco, onboard dining is a big selling point, with galleys on many boats staffed by cooks with professional experience.

“The meals were fabulous,” said Steve Tyler, a retired process safety engineer from Kansas City, Mo., who recalled an especially memorable chicken-coconut-cream curry served on the 51-foot catamaran in the British Virgin Islands that he chartered earlier this year with his wife, Laura, and their 19-year-old and 23-year-old daughters. “Our daughters are so busy with their own lives,” said Ms. Tyler, a retired editor. “It was wonderful for all of us to share three meals a day.”

Using a broker

Brokers arrange most crewed charter trips in the Caribbean, especially for first-time passengers, with the standard 15 percent broker’s fee being paid by the boat owner. Brokers can book virtually any yacht with a crew. The best of them, however, tend to work exclusively with charters run either by boat owners themselves or a team dedicated full-time to the boat — what some call true charters — as opposed to bareboat operations with a freelance captain and cook hired for a single trip.

Many websites appear to offer brokerage services, but actually function more as booking sites. “Real brokers talk with clients before booking to get a sense of who they are and what their expectations are for the trip,” said Mr. Grant. “Based on those conversations, they recommend boats and crews they actually know about from prior bookings, personal connections or visits to the annual charter yacht shows.” Many top brokers are members of professional associations like the Charter Yacht Brokers Association or the American Yacht Charter Association .

Matching crew to client is particularly important. In addition to running the boat and cooking meals, crew members act as hosts, concierges and de facto tour guides, and they can be in close quarters with clients, especially on smaller boats.

So, where are you sailing to?

When you consider that there are roughly 7,000 islands in the Caribbean region, choosing one or several for a crewed charter might seem daunting. But the Caribbean’s charter fleet is concentrated in only a handful of locales with the right combination of good sailing and onshore services. Itineraries tend to be similar no matter how big your boat is. In fact, smaller vessels often have an advantage in being able to travel and overnight in shallower, close-in waters that are off-limits to mega yachts.

In the Bahamas, a popular destination that technically lies in the Atlantic Ocean, boats (including power yachts) make trips from Nassau into the Exumas, a chain of 300-plus low islands and cays with few inhabitants and miles of beaches. The U.S. Virgin Islands, with National Park Service sites and other onshore attractions, boasts a significant charter fleet. In the Leeward Islands, Antigua and St. Martin appeal to those looking for serious ocean sailing and, in the case of St. Martin, especially the French side, good food. South of normal hurricane routes, St. Vincent and the Grenadines, a group of 32 cays and small, agricultural islands, sees an influx of charter boats during what is peak hurricane season for many other Caribbean islands.

The top destination by far, however, is the British Virgin Islands, 50-plus diverse islands — some sparsely inhabited, others dotted with resorts and well-known watering holes — whose terrain ranges from green mountains to sugar-sand beaches.

On their separate trips, the Tylers and Kotchicks each hopped around islands like Tortola, Jost Van Dyke and Virgin Gorda, and made the longer sail to more remote Anegada, home to vibrant pink flamingos.

For the Tylers, the British Virgin Islands trip, which ran about $20,000, was likely a once-in-a-lifetime vacation. “It was expensive,” said Laura Tyler, “but definitely worth it in terms of the memories we created.”

The Kotchicks, however, aren’t ruling out another crewed charter. “I’d do it again in a heartbeat,” said Dr. Kotchick. “The only question is where.”

Follow New York Times Travel on Instagram and sign up for our weekly Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2023 .

An earlier version of this article misstated Laura Tyler’s professional background. She is a retired editor, not a family law attorney.

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Open Up Your World

Considering a trip, or just some armchair traveling here are some ideas..

Italy :  Spend 36 hours in Florence , seeking out its lesser-known pockets.

Southern California :  Skip the freeways to explore the back roads between Los Angeles and Los Olivos , a 100-mile route that meanders through mountains, canyons and star-studded enclaves.

Mongolia : Some young people, searching for less curated travel experiences, are flocking to the open spaces of this East Asian nation .

Romania :  Timisoara  may be the most noteworthy city you’ve probably never heard of , offering just enough for visitors to fill two or three days.

India: A writer fulfilled a lifelong dream of visiting Darjeeling, in the Himalayan foothills , taking in the tea gardens and riding a train through the hills.

52 Places:  Why do we travel? For food, culture, adventure, natural beauty? Our 2024 list has all those elements, and more .

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Caribbean

Find Caribbean Crewed Yachts for the Vacation of a Lifetime

The Caribbean is one of the most popular destinations for yacht charters in the world, featuring crystal-blue waters, white-sand beaches, and more than 5,000 islands and cays to explore. With so many islands to choose from, your Caribbean yacht charter itinerary can be tailored to your preferences, giving you the perfect opportunity to island-hop and explore everything the tropical islands have to offer while comfortably kicking back inside luxurious accommodations on the water.

On your private yacht charter , you will be able to explore lively harbors, secluded beaches, tropical rainforests, world-class dive sites, and much more. The possibilities are endless!

Caribbean Yacht Charter Highlights

  • More than 5,000 islands and cays to explore
  • A great winter destination
  • Crystal-clear, sparkling blue waters
  • Long stretches of white-sand beaches
  • Luxury hotels, five-star restaurants, and spas
  • Islands with their own unique cultures and cuisines
  • A large selection of crewed yachts for charter

Showing 1–4 of 91 results

Chakra Profile

282.2ft / 84m

More info

239.6ft / 71m

Sherakhan Yacht

228.6ft / 68m

sycara V main

223.7ft / 67m

Caribbean Yachting Season

The Caribbean high season for yacht charters runs from mid-December to early May, with Christmas and New Year’s the most popular and busiest times of the year. But due to the islands’ locations near the equator, temperatures remain ideal throughout the year, making off-season charters just as enjoyable.

Keep in mind, however, that there is an increased chance for storms and hurricanes during the summer season, mainly from mid-August to mid-November. Most charter yachts leave the area during that time.

Caribbean Crewed Motor Yacht Charters

remember when main

Remember When

162ft / 48m

More info

Sweet Escape

130ft / 39m

unbridled main

116ft / 34m

Caribbean Catamaran Charters

Yacht Bella Vita Front View

105ft / 31m

Catamaran Serenity Now main image

Serenity Now

Karma catamaran

Caribbean Crewed Sailing Yacht Charters

whisper main

Area Guide: Caribbean Charter Destinations

A girl snorkeling in the BVI

Are you ready to explore all that the Caribbean has to offer? There are three main island areas in the Caribbean, all fantastic destinations for Caribbean charter yacht vacations.

The Grenadines

The Grenadines are untouched by mass tourism and industry, and they are the perfect charter destination if you are looking for solitude and you enjoy exploring remote areas. A great combination of lush rain forests and sandy beaches awaits!

This is a great summer charter destination because the islands aren’t usually affected by hurricanes.

The Leeward Islands

Leeward Islands yacht rentals offer the perfect combination of luxury and solitude. You can visit the glitzy islands of St. Maarten and St. Barts one day and get lost in the remoteness and tranquility of Anguilla the next day.

These islands are rich in history and offer great restaurants, upscale resorts, and trendy harbors.

The Virgin Islands

The Virgin Islands are the perfect location for first-time charterers and families because of their calm waters, protected natural anchorages, and short distances between the islands.

The BVI are a great destination for a catamaran or sailing yacht charter. Caribbean locations here have constant yet mild trade winds year round, and the area offers fantastic diving and snorkeling.

Where Can I Charter a Yacht?

When you choose Worldwide Boat as your Caribbean yacht charter broker, we can help you charter a luxury boat anywhere in the Caribbean or anywhere else you’d like to go, from the Mediterranean to Alaska to the Galapagos Islands.

How Do I Book a Private Yacht?

The best Caribbean yacht charters can be booked in just a few easy steps:

  • Choose our experienced yacht charter specialists to assist you through the process of booking a yacht.
  • Search by destination or by boat, or use our advanced search tool to filter your options by the number of guests, yacht type, destination, and/or your budget.
  • Pick the option that best fits your needs and your dream vacation.
  • Reserve your yacht by signing a contract with the yacht owner.
  • Enjoy your vacation!

How Much Does it Cost to Charter a Yacht in the Caribbean?

Weekly rates for Caribbean boat charters are dependent on a number of factors, including the type of yacht, the season, and your destination. Motor yachts, for example, typically range from $15,000 (yachts up to 80 feet) to $150,000 or more (yachts over 150 feet) per week.

During the Caribbean high season (Christmas, New Year’s, and January/February), yacht charter Caribbean prices tend to increase slightly. Areas with large charter fleets, like St. Martin, tend to have more competitive pricing than areas with smaller fleets.

How Much Does it Cost to Charter a Catamaran in the Caribbean?

Most catamarans offer all-inclusive rates, which start at $10,000 for catamarans under 50 feet and run up to $50,000 or more for catamarans of 80 feet or more. The Caribbean is an ideal destination for a catamaran charter, and across the region, you’ll find a variety of sailing and power cats available for charter.

Ultimately, the cost of a catamaran charter is dependent on the time you visit, where you go, local taxes, and the number of ports you visit. A luxury yacht charter in the Caribbean’s high season (New Year’s or Christmas) will cost significantly more than a catamaran charter in summer.

Can I Rent a Yacht for a Day?

Rates for yacht rentals are usually weekly, but when you talk to a Caribbean yacht charter broker at Worldwide Boat, we can look at your budget, plans, and interests to help you get the best experience possible.

Caribbean Yachting Hotspots

Caribbean sailing charters give you access to white-sand beaches and laid-back island vibes, but they can also offer action-packed itineraries. From island-hopping and hiking to snorkeling and cliff-jumping, adventure awaits on a Caribbean yacht charter!

Some of the region’s must-see destinations include:

  • St. Martin : Known for its upscale eateries and amazing cuisine, as well as high-end spas, shopping and casinos, St. Martin is the yachting capital of the Caribbean. This island is part French and part Dutch, and it’s close to islands like St. Barts and Anguilla, making it a favorite jumping-off point for island-hopping adventures.
  • St. Barts : St. Barts (sometimes called St. Barths) beckons A-listers to its posh beach clubs, fashionable shops, and five-star eateries. Visitors will find a collection of truly spectacular powdery beaches, Michelin-starred restaurants, and excellent shoreside amenities, all within cruising distance of St. Martin.
  • Antigua : Antigua epitomizes the relaxation and bliss of the Caribbean. Known for its 365 beaches (one for every day of the year), the tiny island is a sailor’s dream, offering warm waters, steady winds, safe anchorages, and a lively regatta calendar.
  • Grenada : Grenada is revered for its beautiful beaches, abundant marine wildlife, and vibrant cuisine (spiced with local nutmeg, mace, and allspice). Spend a day relaxing on Grand Anse Beach, which is consistently ranked one of the best in the world. Island-hop to neighboring isles like Petite Martinique, or spend a day snorkeling one of Grenada’s famous reefs.
  • Anguilla : Anguilla is one of the most tranquil Leeward islands. Escape to Dream Bay or one of the numerous nearby coral cays for some supreme R&R. A diving and snorkeling mecca, Anguilla is home to some of the Caribbean’s best shipwreck dives. Plus, the island boasts a calendar of must-see festivals and events, including a jazz festival in November and Carnival in August.

Why Charter a Yacht in the Caribbean?

The best Caribbean yacht charters offer a bit of everything: Relaxation, sun-soaked beaches, delicious culinary treats, refreshing rum-infused cocktails, and calm waters for cruising. Here are some highlights:

The Inescapable Beauty of White-Sand Beaches

Caribbean beaches have almost a mythical quality to them. It’s no wonder explorers were once willing to board wooden ships and travel thousands of miles just to see them in person.

Every island offers a selection of untouched and charming beaches for you to explore. From one-of-a-kind places like “Pig Beach” in the Bahamas to the cosmopolitan Great Bay Beach in Philipsburg, St. Martin, the beaches across the Caribbean offer legendary sights and attractions.

Colorful Celebrations and Friendly Faces

The Caribbean is known for its parades, bars, nightclubs, and parties, not to mention world-famous cocktails. When you want to step off of your luxury yacht charter, Caribbean shores and islands offer a world of fun to immerse yourself in.

A few must-see events include the St. Barth’s Bucket (if you’re into superyacht racing), the annual Carnival celebration, and the St. Lucia Jazz & Arts Festival .

Amazing Wildlife and Adventure

If snorkeling in vibrant and colorful coral reefs, diving into underwater museums, or parasailing over clear waters are some of the items on your bucket list, you can certainly get it all done during your visit to the Caribbean.

You’ll find a variety of unique adventures, from the underwater sculpture park of the Grenadines to the natural seaside baths in Virgin Gorda and hiking the Pitons in St. Lucia. The Caribbean gives you to plenty of chances to get outside and enjoy yourself.

Nonstop Relaxation

Because the area is so close to the equator, the Caribbean offers warm weather to lounge in all year round. Feel pampered aboard a luxury crewed rental yacht, and then feel calm while sinking your toes into soft, powdery white sand. Enjoy the spas, rum cocktails, and quiet, isolated beaches: Charter guests can experience supreme relaxation in the Caribbean.

Book Your Caribbean Charter With Worldwide Boat

Discover the beauty of the Caribbean with a luxury crewed yacht charter. Contact a broker with Worldwide Boat today to learn more about available yachts and itineraries for the Caribbean.

Last edited by Katja Kukovic

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Turquoise Yacht

182ft / 54m

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142ft / 42m

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Caribbean Sailing Vacations

Get ready to hoist the sails on a Caribbean sailing adventure. Whether you are island hopping or gliding along the coast, with 9 sailing vacation packages lasting from 3 days up to 22 days, we have made finding the right sailboat tour a breeze! Click here to see all sailing trips .

9 Caribbean sailing trips

Sailing through the marvellous Caribbean Tour

  • Christmas & New Year

Sailing through the marvellous Caribbean

Grenadines Experience Tour

Grenadines Experience

Discover the hidden treasures of the Caribbean Tour

Discover the hidden treasures of the Caribbean

Puerto Rico Experience 4Days/3Nights Tour

Puerto Rico Experience 4Days/3Nights

3 Days Dominican Republic Expedition Tour

3 Days Dominican Republic Expedition

Hidden Charms of the Caribbean - White Bay, Jost Van Dyke, British Virgin Islands Tour

Hidden Charms of the Caribbean - White Bay, Jost Van Dyke, British Virgin Islands

Yoga Sailing in British Virgin Islands Tour

Yoga Sailing in British Virgin Islands

Sailing adventure in the U.S. Virgin Islands Tour

Sailing adventure in the U.S. Virgin Islands

Catamaran Cruise: Adventure in Martinica and the Tobago Cays Tour

Catamaran Cruise: Adventure in Martinica and the Tobago Cays

Travel styles.

  • 10 Best Sailing Holidays & Trips 2024/2025

International Versions

  • Deutsch: Karibik Segelreise Rundreisen
  • Français: Caraïbes : Circuits navigation 2024/2025
  • Español: Vela Circuitos en Caribe
  • Nederlands: Zeilen Rondreizen in Caraïben
  • Sailboat rental in the Caribbean
  • Boat rental
  • Sailboat rental

Rental Sailboat BENETEAU OCEANIS 48 Tortola

Sailboat BENETEAU OCEANIS 48 14.63m 80hp  (2018)

Rental Sailboat Bénéteau Oceanis 54 - 3 + 1 cab. British Virgin Islands

Sailboat Bénéteau Oceanis 54 - 3 + 1 cab. 17.12m 110hp  (2024)

From $687 per day.

Rental Sailboat BENETEAU OCEANIS 41.1 Saint Thomas

Sailboat BENETEAU OCEANIS 41.1 12.43m 45hp  (2018)

Rental Sailboat Bénéteau Oceanis 41.1 Saint Thomas

Sailboat Bénéteau Oceanis 41.1 12.00m 45hp  (2018)

From $272 per day.

Rental Sailboat Moorings 46.3 Road Town

Sailboat Moorings 46.3 14.60m 57hp  (2019)

From $471 per day.

Rental Sailboat Moorings 46.3 Road Town

From $516 per day

Rental Sailboat Moorings 46.3 Road Town

From $573 per day

Rental Sailboat Moorings 46.3 Road Town

Sailboat Sunsail 51 15.38m 75hp  (2018)

From $898 per day.

Rental Sailboat Sunsail 410 Road Town

Sailboat Sunsail 410 12.35m 40hp  (2019)

From $342 per day.

Rental Sailboat Sunsail 410 Road Town

Sailboat Moorings 382 11.50m 29hp  (2018)

From $393 per day.

Rental Sailboat BENETEAU FIRST 40.7 Road Town

Sailboat Beneteau First 40.7 12m  (2008)

From $374 per day.

Rental Sailboat JEANNEAU Sun Odyssey 349 - ZAURAK British Virgin Islands

Sailboat JEANNEAU Sun Odyssey 349 - ZAURAK 10.34m 21hp  (2018)

From $720 per day.

Rental Sailboat  Beneteau Oceanis 48 Road Town

Sailboat Beneteau Oceanis 48 14.00m 80hp  (2017)

From $1,163 per day.

Rental Sailboat Moorings 42.1 Road Town

Sailboat Moorings 42.1 12.43m 45hp  (2019)

From $443 per day.

Rental Sailboat Sunsail 46 Mon Road Town

Sailboat Sunsail 46 Mon 14.60m 80hp  (2019)

From $432 per day, explore the caribbean by sailboat.

There’s no better way to experience the Caribbean than by sailboat. With over 7,000 islands and islets, the Caribbean is a sailor’s paradise. The warm, turquoise waters and constant trade winds make it the perfect sailing destination. It's no wonder why so many people choose to rent a sailboat to island hop and explore this beautiful part of the world!

The Caribbean islands are home to some of the most stunning sailing destinations in the world. From the British Virgin Islands to Grenada , there’s a destination for every type of sailor. The white sand beaches and crystal-clear waters are breathtaking, and the lush tropical landscapes are simply unforgettable. Whether you’re looking for a romantic getaway, a family vacation, or a sailing adventure with friends, the Caribbean has it all.

Chartering a sailboat in the Caribbean is easy with Click&Boat. We offer a wide variety of sailboats to choose from. Our charter fleet includes boats of all sizes, so whether you’re traveling solo or with a large group, we’ve got you covered. Connect with local Caribbean sailboat owners to create your dream sailing experience.

With Click&Boat, you can find the perfect boat for your needs and budget. Use our price filter when searching for your sailboat rental in the Caribbean to find one that fits within your budget. Don't miss out on the opportunity to explore the Caribbean by sailboat!

Why should I rent a sailboat in the Caribbean?

There are many reasons why renting a sailboat in the Caribbean is the perfect way to explore this beautiful part of the world. First and foremost, sailing is the best way to experience the Caribbean's natural beauty. With so many islands and islets to explore, there's always something new and exciting to discover. Whether you're looking for a secluded beach, a hidden cove, or a lively port town, a sailboat gives you the freedom to explore at your own pace.

Sailing in the Caribbean is also an incredible adventure. The constant trade winds make perfect sailing conditions, and the warm, clear waters are perfect for swimming, snorkeling, and diving. With so many islands to choose from, you can plan your perfect sailing itinerary, and experience a different island and culture every day.

Click&Boat has ideal sailboat options for you, no matter if you’re an experienced sailor or a novice with the option to rent with or without a captain. Whether it’s your first time stepping on a sailboat or if you are an expert sailor, you can find a boat that suits your needs.

How much does it cost?

The cost of renting a sailboat in the Caribbean varies depending on several factors, including the location, the length of rental, the size and make of the sailboat and more. Generally, the cost of renting a sailboat for a day in the Caribbean can range from $300 to $800, depending on the boat's size, features, and location. For a week-long rental, the cost can range from $2,800 to $4,200, on average.

It's important to note that the cost of renting a sailboat in the Caribbean can vary significantly depending on the time of year you plan to sail. During peak season (typically November through April), prices tend to be higher, while off-season rentals can be more affordable. Additionally, some locations, such as the British Virgin Islands, may have higher rental prices due to their popularity and limited availability.

When renting a sailboat in the Caribbean, there may be additional costs, such as captain and mooring fees. However, despite these additional costs, renting a sailboat in the Caribbean can still be a one-of-a-kind way to experience this beautiful part of the world.

When is the best time to go?

Sailing in the Caribbean is possible year-round, but the best time to go depends on your preferences and priorities. If you're looking for calm waters and consistent weather, the best time to go is during the high season, which runs from December to April. During this time, you can expect dry weather, calm winds, and clear waters, making it the perfect time for island hopping and exploring the region's stunning beaches.

However, if you're looking for a more affordable and less crowded sailing experience, the shoulder season (May to November) might be a better option. While you might encounter more rain and occasional tropical storms during this time, you'll also enjoy lower prices on yacht charters and have more anchorages and beaches to yourself.

The harbors in the Caribbean

The Caribbean is known for its stunning beaches, balmy weather, and vibrant culture. But it's also a great place to go sailing and explore the many islands of this beautiful region. If you're looking for a sailboat charter in the Caribbean, there are plenty of options to choose from.

Here is a list of different harbors and marinas where you can dock your boat and enjoy exploring the Caribbean:

  • Simpson Bay Yacht Club & Marina: This marina on the Dutch side of St. Martin is a great starting point for exploring the beautiful waters of the Caribbean.
  • Rodney Bay Marina: Located in St. Lucia, this marina is a popular destination for sailors, offering easy access to nearby attractions and beautiful anchorages.
  • Antigua Yacht Club: This historic yacht club in Antigua is a must-visit for sailors, with a beautiful clubhouse and world-class facilities.
  • Soper’s Hole Marina: This marina in Tortola is a popular destination for sailors in the British Virgin Islands, with its lively atmosphere, restaurants, and easy access to nearby beaches and anchorages.
  • Blue Lagoon Marina: Situated in St. Vincent in the Grenadines, this marina is a popular destination for sailors, with its beautiful scenery, nearby beaches, and access to stunning sailing destinations like Bequia and Mustique.

What are the best places to sail to in the Caribbean?

The Caribbean is home to some of the most beautiful sailing destinations in the world, with a wide variety of islands and destinations to explore. Whether you're looking for secluded beaches, lively towns, or stunning natural beauty, there's something for everyone in the Caribbean. Here are some of the best places to sail to in the Caribbean:

  • Antigua : Known for its 365 beaches, Antigua is a popular destination for sailors looking to explore its turquoise waters and charming towns.
  • St. Lucia : This lush island boasts stunning natural beauty, from its iconic Pitons to its black sand beaches and rainforest.
  • Tobago Cays: This group of small, uninhabited islands in the Grenadines and St. Vincent is a true paradise, with crystal-clear waters and plenty of opportunities for snorkeling and diving.
  • British Virgin Islands: A sailor's dream destination, the BVI offers everything from secluded anchorages to bustling beach bars and restaurants.
  • Grenadines: This chain of islands is known for its pristine beaches, crystal-clear waters, and laid-back vibe, making it a perfect destination for a relaxing sailing vacation.

Other great destinations to explore in the Caribbean include the Bahamas, St. Martin, the Dominican Republic, and many more. No matter where you choose to sail in the Caribbean, you're sure to have a memorable experience.

Renting a sailboat with or without a captain

Another great reason to charter a sailboat in the Caribbean is the availability of skippers. If you're new to sailing, a captain can make all the difference. They'll know the best spots to go and which tides to avoid, so you can focus on enjoying yourself. Plus, they'll handle all the logistics so you can just enjoy the sailing.

But if you're an experienced sailor and are looking to take full control of your vacation and enjoy the open sea, you should consider going on a bareboat charter! Before setting sail make sure you have the right documents.

What brands or models can I rent?

Whether you choose to charter with a private or professional owner, a sailboat rental in the Caribbean has never been so easy. With Click&Boat, the world’s leading boat rental service, book the boat of your dreams whether it be a bareboat charter or a crewed yacht!

Rely on the best prices, an internal messaging tool for owners and renters, as well as a knowledgeable team of advisors ready to help- because booking shouldn’t be a hassle.

Choose to set sail with your favorite shipyard Jeanneau, Beneteau, or DuFour, and discover the islands of the Caribbean, in comfort and style.

Sailing boat rentals in the Caribbean

  • Nautal  / 
  • Rental Sailboat  / 
  • Rental sailboat Caribbean

Sailboat Rental in the Caribbean

The Caribbean is an idyllic island destination with a vibrant and authentic culture. With a warm tropical climate through winter, steady sailing winds and a range of some 7,000+ outstanding islands to hop between, you can choose everything from uninhabited and remote outcrops to bustling port towns with a swinging nightlife for your sailboat rental in the Caribbean. Although there's plenty of smooth and easy sailing to be had in the Caribbean, more adventurous opportunities await in areas like St. Martin, with open-water stretches and remote anchorages. You can choose from a wide variety of Caribbean sailboat rentals at good prices for your next sailing adventure.

A sailing paradise, paired with rich cultures, cuisines and traditions, the Caribbean is full of adventures and beautiful stretches of coastline where you can sail with your friends and family. No matter where you go, we can guarantee you a holiday full of adventure, when you go sailing in the Caribbean. Sail the British Virgin Islands and anchor in idyllic bays where you can stop for lunch or a cocktail on the beach. Snorkel with the tropical fish and turtles in the Bahamas and even encounter a swimming pig, or two! (Yes! We’re not joking!) Let yourself go as you sail with the wind in your hair and admire a constant panoramic view of breathtaking nature at its best. Rent a sailboat in the Caribbean!

How to Rent a Sailboat in the Caribbean

Sailboat rental in the Caribbean is easy and will only take a few minutes. Many visitors will choose to charter a sailboat for a week or more, either with a skipper or without, to fully explore the best of the Caribbean. As a region of colonial heritage, each island offers a unique blend of cultures. Whether that's Anglophone areas like the British Virgin Islands or Francophone Guadeloupe, it's best to choose one of the island areas to explore. You can choose to circumnavigate larger islands like Puerto Rico or stick to archipelagos and island-hopping.

How much does it cost to rent a sailboat in the Caribbean?

There are many different factors that can affect the cost of sailing the Caribbean seas, including the size, capacity, and type of boat, the season when you want to sail, the duration of your trip, and the number of people on board.  The price of Caribbean sailboat rentals will also be affected by whether or not you want to set sail with a skipper, as well as which extra services you want to add to your charter.  For example, you can usually choose to add a crew and watersports equipment to your charter for an additional charge.  

In general, though, sailing in the Caribbean will cost you at least $363 per day or $2542 per week in high season, and a minimum of $186 per day or $1304 per week in low season.

Can you go sailing in the Caribbean with or without a skipper?

Yes, it is possible to find a sailboat rental in the Caribbean either with or without a skipper.  However, you must keep in mind that if you want to charter without, you must be in possession of the appropriate licence.Sailing the Caribbean seas with a skipper and maybe even a crew is perfect for those who want a holiday where they only need to sit back and relax, watching as the spectacular shorelines of the Caribbean go past.  However, if you are someone who likes a little more adventure, bareboat Caribbean sailboat rentals where you can be the captain of your own boat will be a dream come true.

Sailing areas in the Caribbean

The Caribbean is a sailors playground, with an unlimited number of routes and potential itineraries. The British Virgin Islands may offer the best flexibility, with many islands within close distance from each other, offering plenty of opportunities to sail between 25 islands and take day excursions between glorious beaches and coves to a wealth of well-maintained ports such as Nanny Cay, Inner Harbour and Joma Marina. Alternatively, Grenada, St. Vincent and the Grenadines remains another favourite destination for experienced sailors, with gentle crystalline waters, alluring cays and paradisical islands. You should also consider Antigua and Barbuda, an area famed for its open sea races with plenty of small islands to visit.

Sailing boat rentals in the Caribbean are a popular choice of boat and can be found in the following areas of the Caribbean:

  • British Virgin Islands
  • Saint Martin
  • Saint Vincent and the Grenadines
  • Antigua and Barbuda
  • Saint Lucia

Itinerary Ideas in the Caribbean

Lacking inspiration for your sailboat rental in the Caribbean or simply need some tips? Check out our Nautal blog for sailing routes around the BVI, Martinique, Guadeloupe and much more! We calculate nautical miles in our routes and give restaurant recommendations in addition to other random facts and cool things you can do in the area.

Climate and Sailing Conditions in the Caribbean

Our favourite time of year is spring and early summer, from March to June, when the islands are in bloom and are a pleasure to sail. The trade winds are perfect at this time of year, though Christmas and Thanksgiving are also popular times of year for sailboat rentals. We do not advise sailing in August and September as this is known as hurricane season and various areas are not safe during this time of year. 

When is the best time to rent a sailboat in the Caribbean?

As long as you avoid sailing in the Caribbean between August and September, you are bound to have a fantastic time.  Although many people look for a sailboat rental in the Caribbean over the winter months, we actually advise going in Spring and early summer.  From March until early June, the weather will be perfect for sailing and there also shouldn’t be too many tourists.  The reduced number of people means that you should be able to find better deals on boats.

How to get to your sailboat rental in the Caribbean?

The best way to reach the islands is usually by plane, or alternatively you can rent a sailboat in Miami or in the near Florida and sail to Caribbean areas such as The Bahamas.  Many islands have international airports and you can fly directly or find connection flights. 

Charter another boat type in Caribbean

Are you interested in other boats besides Sailboat in Caribbean? Search for other boats to charter on our website

Better Sailing

Best Sailing Routes in the Caribbean

Best Sailing Routes in the Caribbean

Sailing to the Caribbean is a must experience for all sailors. Warm breezes, crystal pure cerulean waters, and unspoiled natural scenery. The water calls to all of us, and with all these spectacular destinations in the Caribbean Sea, you have so many choices for a sailing itinerary. These islands are the ideal sailing location for everybody. Even if you are a beginner you can do it depending on which place you will depart from. With varying levels of experience on deck, some beginners choose to take a skipper onboard. Alternatively, if you have adequate experience you can certainly do it on your own. In any case, the Caribbean is a sailing destination that combines a plethora of choices for all kinds of sailors. And, that’s why it is the most popular destination among boaters. So, let’s move on and see the best sailing routes in the Caribbean. Keep reading!

Best Time to Visit the Caribbean

The Caribbean Islands lie in the heart of the tropics, stretching almost 2,500 miles long but only 160 miles wide. This feature gives them a year-round feeling of everlasting summer. Swimming, snorkeling, and kayaking are always in season because the water temperature stays approximately 80 degrees throughout the year. The Caribbean’s hurricane season runs from July to November. September and October are hurricane season’s peak months. The islands in the hurricane belt, particularly those in the north, such as the Bahamas, Cuba, and Turks & Caicos, are the most vulnerable. Those who sail on the edge of the hurricane belt or to the south of it are more likely to pass by it.

From winter to summer, air temperatures oscillate between 70 and 90 degrees Fahrenheit (between 21.1 and 32.2 degrees Celsius). However, summer months have the highest temperatures and humidity, whilst winter months are the driest and sunniest, with lower humidity. Throughout the year, there may be a few afternoon rain showers. In other words, the best season to visit the Caribbean is from late December until early May. This means after the hurricane season and before the misty months of early summer. 

Although the Caribbean is a great place to sail year-round, except during hurricane season in August and September, the greatest time to sail the Eastern Caribbean from St. Thomas to Grenada is from March to June. Note also that early summer in the Caribbean is just as pleasant as it is in North America. There are fewer tourists, fewer squalls, fewer clouds, and more consistent weather patterns. Also, the weather is the driest from December to April/May, with temperatures averaging between 25 and 30°C. So, the most popular time to visit the Caribbean is during the winter when visitors come to the region for a dose of sun.

In general, sailors love the Caribbean’s low season, which runs from May through October. The weather is typically humid around this season, with a higher probability of rain. But, you’ll still get plenty of sun and warm temps. If you’re a nature and culture enthusiast, then the turtle nesting season or local festivals occur during these months. Moreover, between May and October, there are fewer tourists and lower rates.

Keep in mind that between the middle of May and the middle of June, a bizarre phenomena can occur when Sahara sands from Africa drift over the ocean, creating hazy conditions in the Caribbean’s normally crystal clear horizon. However, because these are the summer months in North America, it is still a popular season to visit the Caribbean, with nice everyday temperatures and a diverse range of activities to select from.

The trade winds quiet down from March to June, allowing boats to access anchorages and islands that would otherwise be difficult to reach in severe, windy weather. Bear in mind that in the Leeward Islands, the islands of Saba and Statia boast deep, exposed anchorages. So, if the wind drives you onto the beach, it’s difficult to anchor safely in 100ft of water. Generally, boats only visit Saba and Statia in calm weather to avoid dragging the anchor. As a result, there are more anchorage opportunities in early summer when the weather is quiet and steady. In early June, for example, you can easily explore the entire eastern side of Martinique. Also, on the windward side of Martinique, there is a lagoon between the outer reef and the mainland that is suitable for cruising throughout the winter.

Note that the majority of Caribbean anchorages are shallow, sandy, and safe, and are mainly in the lee of the islands on the western side of the chain. There, easterly tradewinds are frequently blowing. Also, the wind tends to come from the east. It’s also worth noting that the island chain stretches from Florida to Venezuela, north to south. As a result, the tradewinds strike the chain at a right angle. Therefore, whether sailing north or south up or down the island chain, the wind is on the beam.

Sailing in Barbados

Barbados is the easternmost island of the Lesser Antilles. It is in the western area of the North Atlantic and 62NM east of the Windward Islands and the Caribbean Sea. Barbados, a beautiful coral island, is only 166 square kilometers in size and is located 98 miles east of the West Indies. Barbados’ vast shoreline hides subterranean caves and underground lakes in addition to its unending white sand beaches. Above ground, but underwater, you’ll find some of the best snorkeling in the world, with friendly sea turtles aplenty. Not to mention the island’s stunning tidal pools and the world-class surfing. Barbados has a very rich culture and history in addition to these beautiful natural occurrences. While you dock your boat in one of the picturesque beach villages, go for a stroll and explore some of the historic settlements. Here are some tips to use when sailing in Barbados:

  • Depending on where you’re sailing to Barbados you have plenty of options to choose from. For instance, you might be doing an Atlantic Crossing from Spain or from the Azores. Or, you might already be in the Caribbean Sea or in the Gulf of Mexico. If sailing from Europe then it is possible to make your first stop in Barbados. If you’re sailing in the Caribbean Sea you can organize your voyage according to your preferences and of course, according to the weather. It’s approximately 120NM if you’re sailing from Martinique to Barbados. If your starting point is the USA, e.g. Miami, then you will first stop in the British Virgin Islands, Guadeloupe, Martinique, etc.
  • The best place to visit is Bridgetown. Barbados is frequently visited first since it is located east of the Windward Islands and requires a 60-mile beat against the trade winds if visited later. One of Barbados’ principal marinas is located in Port St. Charles on the NW coast of the island. It can provide overnight protection for your boat if you’re on a longer voyage. Although the port is also home to a high-end resort, but Heywoods Beach, like all Barbados beaches, is available to the public. Note that the island’s main anchorage is in Carlisle Bay near Bridgetown. 
  • Another marina where you can stay the night is Port Ferdinand .
  • As you travel south along the coast, you’ll come across Reeds Bay, a peaceful and pristine beach perfect for a relaxing swim.
  • The only safe cruising region is along the sheltered west coast; the east coast is rocky and exposed to Atlantic swells, therefore it should be avoided.
  • While Barbados is the closest landing for boats crossing the Atlantic on the trade wind route, many skip it in favor of better-developed yachting infrastructure at Saint Lucia, Grenada, or Antigua. Barbados, on the other hand, is working to remedy this issue, and clearance and docking facilities are constantly increasing.
  • If you leave your boat in  Alleynes Bay , go for a cocktail in  Ju Ju’s  bar.
  • Make your way to the seas off Folkstone Marine Reserve and snorkel its magnificent seas if you’re looking for a relaxing afternoon. Sea anemones, sea lilies, corals, and sponges can be found among the fish.
  • Head onto the beach for lunch at the gorgeous Sandy Lane Hotel and a few water sports on the world-famous Sandy Lane Bay.

Best Sailing Routes in the Barbados Caribbean

Sailing in the Bahamas

The Bahamas are surrounded by over 30,000 square kilometers of stunning azure blue water. It is one of the world’s most popular sailing locations, with thousands of visitors each year. In an area larger than Florida, there are 700 distinct islands strewn across the ocean. A sailboat is the greatest way to go if you want to discover as much as possible. In the Bahamas, there are numerous anchorages and ports to select from. The region boasts a wonderful sea, national parks, and secluded islets and coves, in addition to spectacular scenery and a nice environment. These are the best sailing routes in the Bahamas:

  • Sailing to the Abacos: The Abacos, which are located near Grand Bahama Island, are home to the villages of Hopetown, Marsh Harbor, and Man of War. These are the greatest areas in the Bahamas for those who love crowded places and large structures, as they offer a wide choice of amenities such as hotels, nightlife, attractions, museums, shopping, and restaurants. When sailing to the Abacos, it’s best to leave Palm Beach and sail 60 miles across the Gulf Stream before docking at the Old Bahama Bay Marina in West End. The second phase of your journey will take you to Green Turtle Cay, which is around 100 miles away. You can continue sailing for around 20 miles to Marsh Harbor, which is located in the heart of the Abacos. Alternatively, you can sail for about 10 miles to the south to Little Harbor where there are smaller marinas and secluded anchorages.
  • Sailing to the Exumas: This cruise is regarded as one of the best in the Bahamas. Set sail from Fort Lauderdale or Miami for a 50-mile journey to Bimini. After there, you can travel 80 miles south to Chub Cay. Then continue sailing across the Tongue of the Ocean to Nassau, which is about 40 miles away. Then consider going to the Northern Exumas, but keep an eye out for the reefs near Nassau Harbor’s southern edge. The Highbourne Cay Marina, Sea Park at Warderick Wells, and the Exumas Land Marina are all located in Northern Exumas.
  • Sailing to Bimini: If you want to go to Cat Cay or Bimini in the Bahamas, you’ll need to travel south of Miami. For instance, consider Key Largo. If you’re sailing to the Bahamas, though, Fort Lauderdale or Miami are better possibilities because they can take advantage of the Gulf Stream. Sailing to Bimini, Cat Cays, or any other island in the western Bahamas is around 50 miles. These islands will offer you a flavor of what to expect as you travel farther into the Bahamas, as well as a feel for crossing the Gulf Stream. To the north of Cat Cay, you can dock your sailboat behind Gun Cay.

Best Sailing Routes in the Bahamas Caribbean

Sailing in the British Virgin Islands

The Virgin Islands are a group of islands in the Leeward Islands’ northern region. The American and British Virgin Islands are divided into two parts. The British Virgin Islands are part of the United Kingdom’s overseas territories. It is made up of more than 50 islands, although only 16 of them are inhabited. Tortola, Virgin Gorda, Anegada, and Jost van Dyke are the largest islands; all but Anegada are volcanic. Peter Island, Beef Island, Salt Island, Cooper Island, and Norman Island are among the smaller islands. Road Town, the archipelago’s capital, is located on Tortola. The location is known as the Caribbean Sea’s sailing capital for a reason: it is the area’s most popular sailing site, where anyone, regardless of expertise, may choose their favorite route. Here are some tips and route suggestions for the British Virgin Islands:

  • Antigua to BVI route: From the south and west, you will sail to the British Virgin Islands according to this route. From Antigua you will arrive in Virgin Gorda, the archipelago’s easternmost point, after passing via the Leeward Islands. Because the journey from Anguilla to Virgin Gorda is somewhat long, you have to plan adequately. The Anegada Passage, known for its difficulties, can be your first stop. You can spend a week or so in the British Virgin Islands, where you can sail from port to port and island to island. Nanny Cay on Tortola is the ultimate destination.
  • Puerto Rico to BVI route: You can set sail from Fajardo, one of Puerto Rico’s main harbor cities. You can stop in the Spanish Virgin Islands first, then travel to the British Virgin Islands through the American Virgin Islands, navigating toward the east. This is a lovely journey with distinct ports at each stop. The suggested route goes like this:   Puerto Rico, Fajardo, Puerto del Rey Marina – Cayo Icacos 8NM, Cayo Icacos – Culebra, Ensanada Honda 25NM. Then,   Ensanada Honda – Saint Thomas, Crown Bay Marina 23NM, Crown Bay Marina – Saint John, Cruz Bay 12NM, Cruz Bay – Jost van Dyke, Great Harbor 9NM, Great Harbor – Tortola, Frenchman’s Cay 7NM, Frenchman’s Cay – Peter Island, Little Harbor – Nanny Cay 11NM. Note that this route can take you from one week to 15 days according to your schedule and preferences.
  • Of course, there are numerous options for a sailing trip to the British Virgin Islands. You can set sail from a nearby island, such as St. Croix or Anguilla, or a more distant island, such as Guadeloupe or Grenada. Starting at the Turks and Caicos Islands, there is a southeast route that takes you all the way to the archipelago along the northern coast of Puerto Rico, which can be challenging but wonderful for many sailors. This journey will take at least two weeks to complete, with most of your time spent on the boat. The British Virgin Islands, on the other hand, are so lovely that even a short round trip in the area will be an unforgettable experience.

British Virgin Islands Caribbean Sailing Routes

Sailing Guadeloupe and Dominica

Guadeloupe is a Leeward Island that is distinguished by its butterfly shape. Grand-Terre, the island’s eastern wing, is home to Pointe-à-Pitre, the island’s largest city and tourism hub. Basse-Terre, the western wing, is less developed and is home to an important national park. The island’s two parts are separated by a small strait known as the Salt River. Marie Galante, which has excellent snorkeling, and the Gosier islet, with its vast coral reef, are also close by. You can also sail to the island Les Saintes and sail around Fort Napoleon on Terre-de-Haut where there are numerous anchorages.

Don’t leave without stopping by Jacques Cousteau’s Underwater Reserve, which is located near Pigeon Island and features a variety of colorful coral forests and rare aquatic species. This underwater realm is regarded as one of the top dive destinations in the Caribbean. Consider heading for Point-à-Pitre on the south side of the island which is less frequented.

Dominica is the world’s second-largest boiling lake and is mostly covered in rainforest. There are numerous waterfalls, springs, and rivers on Dominica. In Dominica’s jungles, some species and animals thought to be extinct on neighboring islands can still be found there. Dominica is a renowned scuba diving destination due to its volcanic nature and lack of sandy beaches. Due to its high drop-offs, healthy marine environment, and reefs, this island country has numerous outstanding diving destinations. Cabrits National Park is one of the numerous protected places on Dominica. Also, Dominica has a total of 365 rivers.

On the northwest extremity of the Island, Prince Rupert Bay near Portsmouth is an excellent harbor. It is also a large, safe anchorage with almost no adverse weather unless you’re in the shallows during an SW wind.  There are a few small bays along the West Coast, such as Miro, Castaways, and Canefield , although they are prone to swells and are only suitable for brief visits in favorable weather. Other beautiful bays, such as Douglas Bay and Soufriere, are popular marine protected areas.

Best Sailing Route Between Guadeloupe and Dominica:

Marina Bas-du-Fort to Les Saintes (18 nm), Marie-Galante (20.55 nm), Marie-Galante to St. Francois (19.9 nm). Sail to Petite-Terre and return back to St. Francois in the evening (10.89 nm). Then, from St. Francis to the Marinor Gosier (18.42 nm), and Gosier to Anse-de-Mai in Dominica (52 nm). Then sail to Portsmouth (5.1 nm) to St Louis in Marie Galante Island (35 nm), and lastly from St Louis to Marina Bas-du-Fort back to Guadeloupe (20 nm).

Sailing Martinique and St.Lucia

Martinique is a jewel of the West Indies, with amazing beaches and natural beauties to explore on your sailing route. Its 350 kilometers of shoreline is a remarkable unique feature and that’s why it is a popular destination among sailors. Large sandy beaches and stunning reefs will take your breath away. Because of the reefs, it is not only a popular sailing location but also a popular snorkeling and diving spot. Martinique’s main departure point is normally Le Marin , which is a terrific place to set sail. Boats often head for Le Marin on the SW corner of Martinique . Sailing north, you’ll come across stunning scenery in a wild and tropical environment. Aside from that, there will be significantly fewer tourists, which is usually a benefit in terms of exploration and relaxation. With 5 moorings in total, you’ll be fine exploring the island and making the most of it. 

Little St Lucia is located in the Eastern Caribbean chain and is known for its magnificent palm-fringed beaches, pristine rainforests, and, of course, the famous Piton Mountains. St Lucia is noted for its champagne sunsets and brilliant starry skies, making it an ideal location for a romantic sailing vacation. You’ll come across waterfalls and luxury marinas, mineral baths, and beach art cafés when sailing along its coasts. Every corner of the island reveals something new and surprising. You’ll also discover that the islanders are exceedingly welcoming and that you’ll be welcomed everywhere you go on the island.

Note that most sailors are drawn to the Eastern Caribbean because of the opportunity to combine open-water, down-island sailing in favorable winds with pleasant days of short passages between islands. You can combine watersport activities, islands’ exploration, and learn about the culture and atmosphere of the smaller islands. The Grenadines, Port Elizabeth, Mustique, and other island gems. Keep in mind that between St. Lucia and St. Vincent is the longest passage, and beyond that are a slew of tropical islands to explore.

Best Sailing route Between Martinique and St.Lucia:

First, set sail from Martinique (Fort-de-France) to Saint Lucia (Castries). The total distance is about 38NM. Then, from Saint Lucia (Vieux Fort) head to Saint Vincent and the Grenadines which is about 54NM. You have plenty of options there as there are 32 islands that you can explore but this will take you more than a month with a tight schedule. However, this is the best route to take: from Saint Vincent to Bequia (9M), Bequia to Baliceaux (13NM), Baliceaux to Mustique (5NM), and Mustique to Canouan (15NM). Then, from Canouan to Mayreau (7NM), Mayreau to Tobago Cays (3NM), then to Petit Saint Vincent (6NM) and Petite Martinique (1NM). Continue to the Union Island for about 5NM and then back to Saint Vincent or directly to Saint Lucia (55NM). Note that this route can be done backward.

The Bottom Line

These are the most common and best routes for sailing in the Caribbean. Of course, you have unlimited options as the Caribbean has more than 700 islands; each one with its own unique characteristics. In general, if your starting point is the USA or the Gulf of Mexico you can combine some of these sailing routes within a 2-months time frame. If you’re crossing the Atlantic and heading to the Caribbean for 3 months you can make the most of it and combine Puerto Rico, BVI, Anguilla, Antigua, Guadeloupe, Dominica, Martinique, St.Lucia, Grenadines, etc. It all depends on your time schedule and preferences. Of course, let’s not forget about the weather! The best time to sail in the Caribbean is from December to May. But, you should regularly check the weather forecast as unexpected tides and currents are likely to occur. And, nautical charts as well.

I hope that this article gave you some ideas about which routes to take in the Caribbean. Wish you all safe & pleasant voyages!

Peter

Peter is the editor of Better Sailing. He has sailed for countless hours and has maintained his own boats and sailboats for years. After years of trial and error, he decided to start this website to share the knowledge.

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PERFECTLY STRANDED IN THE CARIBBEAN

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Florida & Bahamas

sailboat in the caribbean

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Sailing Expeditions with Impact, Adventure & Community

Sail the caribbean with us travel by sail to multiple island nations, fuelled by coconuts and fellow adventurers.

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Caribbean Sailing Winter 2022 /2023

Expedition on | sailing the caribbean sea | west indies, after 5 years of organizing adventure and impact sailing trips we now go bigger and further than ever. and you can join us in the caribbean or across the atlantic.

The Caribbean islands are blessed with tropical rainforests, stunning reef drops, waterfalls and kitesurf and freedive potential. It is as scenic above as below the surface. The Caribbean are a nature lovers playground, full of character!  

With dozens of authentic and unique island nations, the Caribbean calls for exploration time. The way to explore the Caribbean is by sail! With the trade winds from the east and the island chain going from north to south, turquoise waters and hundreds of islands, bay and inlets, sailing conditions are just perfect.  You have to take the sea route to get the best sense of place, reach the best kitesurf, freedive and exploration spots. 

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Discover what it feels like to wake up on anchor, jump in the Caribbean sea first thing in the morning. breathe the healthy ocean air, have the wind in your hair, live simple and resourceful, and explore like the explorers back in the days. Day in, day out….

Dates & Destinations

4) Martinique, St. Lucia, St. Vincent & the Grenadines, Grenada | Dec 21 – 28 | 7 days FULL

5) Grenada, St. Vincent & the Grenadines, St. Lucia, Martinique | Dec 28 – Jan 4 | 7 days

6) Martinique – St. St. Lucia, Vincent & The Grenadines, Grenada, Martinique | Jan 7 – 19 | 13 days

7) Martinique – St. St. Lucia, Vincent & The Grenadines, Grenada, Martinique | Jan 21 – Feb 2 | 13 days | FULL

8) Martinique – Dominica – Guadeloupe | Feb 4 -11 | 7 days | FULL

9) Guadeloupe & Surrounding Islands| Feb 11-18 | 7 days

10-A) Guadeloupe – Dominica – Martinique | 18 Feb – 27 Feb  | 10 days

10-B) Martinique to St. Maarten Fast Sailboat Ferry | 28 Feb – March 2 | 2 days

11) St. Maarten & Surrounding Islands | March 4 – 13 | 9 days

WE FACILITATE AND ACCELERATE​

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Adventure Sailing

Slow travel by sail, powered by wind, ruled by nature. Offshore and remote. On a 100+ year old hands on classic ship. No electrical winches here. With a bunch of 'strangers,'  Expect the unexpected!

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Positive Impact

We strive for minimum negative and maximum positive impact with our preparation & execution. The difference is in the details. 

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Ocean Minded Community

Expand your network with insight and inspiration. We walk the extra mile to unite your soul tribe members on board. Connection and conversation at sea goes deeper in one day than months on land.

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Stories & Skill Building

Learn and expand your seamanship, sailing, navigation, resilience, conscious living, adaptation & social skills. + Introduction to Kitesurfing & Freediving. Exchange skills and stories with fellow crew members

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Conscious Lifestyle

Gather tips and tools, to accelerate your journey to alternative adventurous conscious life on or near the sea. Lifestyle designing by and for ocean nomads.

Explore, Discover, Learn

Sailing in the caribbean.

Imagine jumping into warm turquoise waters just seconds after you wake up. Eating a freshly chopped papaya for breakfast, having consistent 15-20 knot breeze when sailing to the next island, and if we’re lucky spotting a whale or dolphins, do a  boat swing,  hiking up a hill for the view, climbing a palm tree for a coconut, and enjoying a sunset chillax with that coconut and green flash on the horizon. You can work on your swimming skills immersed in the evening bioluminescence, with the starry sky above you making wishes.

That’s just one example of a day on board SV Twister in the Caribbean. Each day you’ll experience something new, whether it’s spotting ocean wildlife, discovering a new island or trying some of the best local Caribbean cuisine.

Ocean Nomads trip are beyond ‘the usual’ sailing holiday. It’s and adventure experience aimed at making the dream lifestyle reality, not just for the time with us but beyond all that. Incorporating the Ocean Nomads values, of community, exploration, and positive impact into the elements of the trip. Ocean Nomads trips are always hands-on, everyone helps with the running of the ship. 

Wherever we go we leave the places cleaner than we find it. Beach clean ups are part of the routine, not ‘just’ incorporated as an event.

This is a muti-adventure trip. But ofcourse, you’re always welcome to chill and read a book or just do nothing, but BEing.

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Background story

Suzanne: “When I started looking into travel by sail, seven years ago now, I had no idea about sailing and I didn’t have connections in sailing either. I struggled to find out how to get into travelling by sail, safely, with little budget and experience, and as I went on I struggled finding ‘my kind’ of people, those purpose and adventure driven wild souls looking for adventure, action and making a positive impact.

For a few years I lived more at sea than land, ‘crewing/hitchhiking’ on about 50 different boats. Good, bad, and priceless experiences. If I learned one thing, it’s the people who make the experience, happy, safe, and meaningful! Caribbean sailing trips are what you make it. On these voyages we walk the extra mile to discover the pure essence of the Caribbean. 

I wrote a book about travelling by sail (Ocean Nomad). And as I couldn’t find my tribe and value-matching vessels, I created it, into what’s now the Ocean Nomads network of which the most fast track ocean nomads lifestyle acceleration are the ocean nomads voyages.

By uniting you, your experiences, connections and stories, at sea, we can reach way further, help more, do more, and be more.  

To reach for the stars, we must surround ourselves with likeminded entrepreneurial salty souls, share knowledge, and inspire and cheerleader each other. So much more is possible if we join forces on our journeys. The best, going on a journey together! I wish for you to see for yourself how beautiful the ocean are! And hopefully ignite the superpower within you to take steps into a conscious nomadic life in or near the sea, and give back to the ocean, our playground, our home, our life. The pursuit of a healthy ocean and lifestyle are one and the same. ” 

I’m looking forward to personally welcome you on board SV Twister in the Caribbean! (on board until leg 9 at least)

Ocean Nomads Lifestyle Accelerator

With Expedition ON Caribbean, we are sailing across the Caribbean Sea on a classic 36 meter schooner originally built in 1902. We visit almost all the island nations, powered by wind, coconuts and the energy of like minded ocean nomads on board. A hands-on ocean adventure discovering ways to live and travel more simple, wild, and pure. 

Experience the ocean nomads lifestyle, get natured, travel remote, explore the unknown, together with an international group of conscious ocean adventurers. Driven by passion and purpose for the love of the ocean.

Jump on board and accelerate your ocean nomads ambitions and lifestyle. With adventure Sailing, Ocean Exploration, Natural Lifestyle, Nomad Community & Ocean Conservation in the mix!

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  10 percent discount for members! Not a Member yet? Join the tribe! (+70 vessels and 100s of nomads in the network)

“The most unforgettable week. The trip preparation and the crew members turned what would otherwise be an adventure into something a special. I took part in two ocean nomads trips so far. To say it was life changing sounds dramatic but it really was. Being able to share time and experiences with people with different backgrounds but of a similar mindset was incredible. I like to think that I can have and help contribute to a similar experience for myself and others as a member of the Flotilla crew.”  – Ben Clipstone

Expedition on impacts the way you approach life, live with nature & love the ocean, we go the extra mile to....

Throughout our expeditions we bring together a unique mix of inspirational individuals talents and knowledge of the group. We release the power from the individual talents and knowledge into the group, for maximum learning experience.

We select participants based on motivation, values, drive, and mindset. For legs of longer than 10 days we additionally interview on the phone to make sure expectations and values are aligned.

Make Ocean Adventure Accessible

No sailing experience is required. We happily teach. We believe that if more people get a chance to experience the ocean and all the magic that comes with it, the ocean wins more hearts. We like for you to see for yourself how beautiful the ocean are. And hopefully ignites a superpower within you to take steps into a conscious nomadic life in or near the sea. Voyages range between 7 days and one month. From offshore sailing to crossing oceans to exploring remote paradise islands. We provide a platform for nature connection, community, research, creation, while going remote. 

Prioritize Safety

The ocean deserves our greatest respect. Sailing remotely is an endeavour not to be taken lightly. Teaming up with Twister allows us to combine professionalism, safety, and adventure, impact and community facilitation. After three offshore collaborations, the only thing we broke were 2 plates. Many certificates are obtained and complied with to pass the safety checks and requirements to take people out offshore. We have highly experienced (and qualified) people on board. This comes with a cost but the rewards are priceless. Offshore we keep contact and update relatives about the trip.

“We must go and see for ourselves!”- Jaqcues Yves Cousteau

Our drive: protecting our playground .

Saving the ocean is at the core of the Ocean Nomads community. The Ocean is the heart of the planet. Water covers more than two-thirds of the Earth’s surface. Sea plants, like Posidonia, produce 70 percent of the oxygen we breathe, and the deep waters are home to wildlife and some of the biggest creatures on earth. It provides us with food, jobs, life, entertainment, and sailing! Without it, we cannot survive. We believe that by getting the ocean into people’s heart, one starts caring more accordingly. The best way? To get you out there and have you experience the magic for yourself. 

Our Caribbean Sailing Trips Dates & Details

Caribbean sailing trips & exploration voyages '22 '23.

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Martinique - Grenada (& Islands in between)

December 21 - 28 7 Days | Euro 1815 (ON Price 1635) FULL

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Grenada - Martinique (& Islands in between)

December 28 - January 4 7 Days | Euro 1815 (ON Price 1635)

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Martinique - Grenadines - Martinique

January 7 - 19 13 Day |Euro 3552 (ON Price 3200)

Offshore kitesurfing in the Caribbean with a sailing crew.

January 21 - Feb 2 13 Days | Euro 3552 (ON Price 3200) FULL

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Martinique - Dominica - Guadeloupe

February 4 - 11 7 Days | Euro 1655 (ON Price 1500) FULL

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Guadeloupe - Surrounding Islands

February 11-18 7 Days | Euro 1655 (ON Price 1500)

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Guadeloupe - Dominica - St. Maarten

February 18-27 10 Days | Euro 2450 (ON Price 2205)

Martinique - St. Maarten

February 28 - March 2 (497 euro) Local & ON discount available

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St. Maarten & Islands Exploration

March 4 - 13 9 Days | Euro 1999 (ON Price 1800)

Giving Back

We are merely visitors and we feel it’s our duty to give back, contribute, and support where we can. In addition to cultivating environmental and social consciousness (see trip values further below) to the best we can, for each booking we donate a percentage to a hand-picked local conservation project.

Little Budget?

We created scholarship opportunities for the small budget determined ocean explorers.  In collaboration with this ship and the costs that come with it we can’t do a full exchange but we can do discounted prices with skill shares, trades and long term nomads. We love to hear what you have in mind via the   Scholarship form.   For pure skill sharing and trading, check out our membership community with +300 nomads & +70 vessel members meeting up and teaming up for ocean impact and adventure.

What's included?

  • Sailing adventure & nature connection
  • A unique and curated mix of adventurous & impact-driven salty souls
  • Food and Drinks (Except Alcohol). All trips are vegetarian. We share cooking & cleaning duties.
  • Being taught the ropes of the ship & seamanship
  • Trip organisation
  • Introduction to Freediving AND Kitesurfing on Leg 4-5-6-7-8 Free discovery course by licensed intructors!
  • Ocean worthy vessel & safety equipment checked and complying with strict requirements
  • Professional qualified and experienced Skipper & Crew
  • Accommodation onboard in a shared cabin*
  • Custom & Clearance fees, Marina fees, marine park fees (if applicable) and fuel
  • Memories for life!

It’s the most luxurious vessel we’ve ever teamed up with. Each cabin has a good size bunk, sink, plug to charge, bed light and window. Cabins are shared with one, two or three fellow Ocean Nomads. You’ll always have your own individual bed.

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Other costs to bear in mind?

  • Transport to and from the boat destination
  • Additional nights spent ashore
  • Personal travel insurance
  • Personal equipment e.g. waterproofs 
  • Personal expenses ashore
  • Ocean Nomads Membership (If not a member yet)
  • A valid Passport!

“In my opinion Ocean Nomads sailing adventure are: 1. A reward for the senses by discovering incredibly beautiful places and breathtaking sceneries. 2. An unbeatable way to get introduced into the world of a sailing lifestyle 3. An open window to learn watching our world and the people from another more conscious perspective. I see Suzanne as an inspirational person who, with her example, inspire others with ideas and proposals to define or redefine life projects and use inner energy for more noble purposes. Our oceans need strong committed people like her to advocate for our natural resources and leave them intact for the generations to come.”  – Jose Perez

About ocean nomads.

With Ocean Nomads we connect ocean people, vessels, projects, and environmental action to facilitate sailboat travel, adventure, impact, and a nomadic and ocean-conscious way of life.

We’re many out there all on similar journeys, dreaming and doing about ocean adventures and to make a positive impact around us. We have brilliant ideas, projects, and dreams. We desire to experience, to learn, to connect, and to be part of something. We’re looking to connect with others honouring simple and sustainable lifestyles. We are concerned by the state of the planet. We want to make a positive contribution and do our bit. The ocean brings us so much. As fanatic users, we are responsible for bringing life back into the blue. But alone we can only do so much. 

Ocean Nomads trips connect people to each other and to the ocean. Nothing brings people together like actually bringing people together. And nothing triggers more than actual experience. We add nature and adventure into the mix, and we have a recipe for creating a big dose of positive energy and accelerating change for a common good. We provide ocean adventure and encourage low-impact travel by sail.

On purpose we don’t plan out everything in detail. We roll with the weather, our intuition and opportunity. With good preparation. 

We live up to the Ocean Nomads’ slow sailing philosophy. We strive to have an onboard environment that inspires adventure and play, with a strong emphasis on hands-on action, health, simplicity, local, teamwork, skill sharing, and environmental consciousness. 

If not now, then when?

A sailing adventure offshore or between countries is not a straightforward endeavour. To be ready to expect the unexpected, careful selection and preparation for a happy, safe, and meaningful voyage is essential. We are ON it! Expedition ON  is a synergetic team-up between SV Twister and Ocean Nomads. SV Twister allows us to safely and responsibly organize adventures offshore. The beauty of a vessel this size allows us to connect more salty souls in one place, away from civilization where we disconnect from everything but each other and nature. These are hands-on active expeditions, with next level participation in the offshore legs. We have a professional captain and crew who’ll be showing us the ropes. Everyone on board is expected to take part in the running of the ship. It’s part of the fun, experience, development and epiphany moment creation. That said, we’ll be many hands on board so there’ll be plenty of room to chill, relax and simply BE.

You can join on or more legs. 

If you ever dreamed about sailing an ocean, visiting remote tropical islands or just an experience like nothing else, this could be it!

“The sailing with such a beautiful ship. It is absolutely breathtaking to sail a tall ship and minimize the use of the motor as much as possible.” – Marc Expedition ON 2021

Trip Values & Expectations

ADVENTURE |  Depending on the destination, the trip includes action, outdoors, play and fun. Our offshore we sail non-stop with everyone being involved in the watches. We do our best to include some hiking or snorkeling (either offshore at 1000s meter deep and/or in an epic anchorage on arrival). On our coastal trips days include a mix of sailing, jumping in the sea, snorkelling, exploring islands, finding treasures, hiking, SUPping/ We try to avoid marinas, so we can be closer to nature.

SPONTANEITY | We run our trips rather spontaneously on purpose. We’re dependent on the weather. We go with the flow, and we may change course to explore what we find on the way. We embrace the art of getting lost. We don’t plan out our routes into detail. On purpose.

SAILING | You don’t need sailing experience. Captains we work with are professionally qualified and teach you the basics, helping you become a competent crew member – or building upon any existing skills you do have. We can sign off miles and give you a reference if you need one. We take care of onboard duties as a group. 

COSTS |  As opposed to other trips we have organized, this expedition has food included in the trip price.

VESSELS | We work with local and sustainably-minded charter companies. This Expedition we work with a vessel of more than 100 years old and still sailing the oceans! It can’t get more sustainable than maintaining that what is already built.

IMPACT | We share adventure and relaxation time, as well as thoughts, tips and ideas about how we can live more simply and sustainably, whilst exploring the natural world. No one of us has the answer, but together we do have. Connection and conversation at sea go deeper in one day than months on land.

LOCAL | We aim to team up as much with locals to learn the best we can about the local situation. Working with a local partner comes with different habits, customs, awareness levels and cultural backgrounds. We stay open and look beyond our ‘eco-bubble’ to plot better routes for positive change.

CONSERVATION  | We aim to give back to the best we can when visiting the places we visit through spending local, leaving places cleaner than we find them and learn and engage with the local community. Also, for each booking of this trip Ocean Nomads donates 50 euro into a local conservation project. 

GETTING THERE | We are aware that many need to fly to join one of our trips, and encourage transport options such as train, bus, ferry and car sharing. We’re actively looking for the best ways to maximize our positive and minimize our negative impact. We recommend booking only one way ticket. You won’t be the first ocean nomads joining a trip, and just keep on going… 🙂

ENVIRONMENT | We do what we can to minimize our environmental impact. We sail as much as we can and use the motor as little as possible. Preparation and doing your part is key. And we encourage and welcome your ideas, tools and tricks on improving our positive footprint.

PROVISIONING |  Collectively we take care of the provisioning and cooking. It’s part of the fun! We don’t organize luxury cruises. We aim to provision as locally as possible, and minimize plastic use. Our trips are vegetarian (fish and meat-free), with occasional opportunities to eat ashore if you struggle with this. We use less freshwater and power than the average sailboat charter. We share thoughts, ideas, and knowledge on no-fridge food preservation, eco-friendly sailboat maintenance, and other positive solutions.

PEOPLE | We make our gathering big enough to guarantee a wonderful mix of inspiring souls, but small enough to drop anchor in the middle of nature. Participants usually don’t know each other, but after days of shared adventure and collaboration, new friendships are made. Many of our previous nomads come back again and again. Ocean Nomads come from all walks of life; we put a lot of effort in creating a diverse mix of people, so that we can learn from each other and pass on inspiration & ideas. Many trip alumni and members have since teamed up for more adventure and impact projects.

TEAMWORK | Sailing is an active way of travel that needs teamwork. We share the tasks, operation, and sailing of the boat. We provision, cook, sail, fix things (if necessary) together as a team. Our trips are not a laid back luxury experience. Hands-on participation creates the adventure, and helps you learn to be a better sailor.

HEALTH | We can only do good if we feel good. Our trips have elements of yoga, breathwork / freedive clinics, healthy and local food provisioning, and lots of outdoor action and adventure. Powered by YOU, our members and crew. 

PEACE | Our trips are not a party experience. We value the mornings and like to maximize daylight for exploring and connecting to nature. Drinking a lot of alcohol ruins this experience and has no place on our trips. We operate a strict no alcohol at sea policy.

ADAPTATION | Boats rock and make noise. Boats are small. People snore. Weather rules. We have limited resources. Adaptability is key.

ACCESSIBILITY |  We know a trip like this is not within financial reach for everyone. It costs considerable money to make this expedition real, in most safe way. But where resources allow we facilitate scholarship opportunities to make an adventure like this accessible for the driven on a budget ones.

Learning by doing, that’s what we strive for. Here are some of the skills you develop on our trips:

SAILING | You’ll learn hands-on everything to become a competent crew member. By the end of the journey you can sail the ship. Our skippers and often also fellow crew members are happy to share and show what to know.

SEAMANSHIP |  Huge part of happy, safe and meaningful ocean nomadic living depends on your seamanship skills.  You can have the biggest bank account but once you’re at sea nothing can be googled or bought. And no person can be hired to fix something. You have to be inventive as situations arise and you’ll learn from experiences along the way. You’ll learn to work with your hands. You learn about the wind, the weather, geography, stars, navigation, sea life, boats, yourself, people, and much more. 

CONSCIOUS LIVING |  Experience resourcefulness. And how you can implement it all into your life. As sailors, we are intricately connected to the ocean on a daily basis. Experiencing sea time daily provides a deep and lasting respect for nature. You’re dependent on it. You experience the power of the wind and the waves, and realise how precious our resources are, such as water, fresh air, power, and fresh vegetables. You will become aware that what might be considered normal ‘back home’, is not so normal on a boat.

The luxuries of living on land: sitting up straight in your bed in the morning, taking a shower lasting more than ten seconds, pouring a coffee of that doesn’t spill, flushing a toilet, a fresh apple in a fruit bowl, sleeping on a bed that doesn’t move, food that stays on the stove, power plugs, getting through your morning routine without four new bruises, doing dishes with warm water, walking more than ten metres, friends to talk to, WiFi, and so much more. All the things we take for granted on land become priceless when you have experienced life without them. 

Sailing makes you a conscious consumer and a more grateful person for every little luxury thing. With limited storage and cooling, food sharing, and adaptation, you have to think about every item you bring on board and why. After a sailing experience you will appreciate every drop of water, fresh fruit or vegetable and a good night of sleep even more.

NATURE AWARENESS|  Most of us spend more time indoors than outdoors. It’s easy to forget the natural world we’re coming from and living in. On the ocean, you face the wind and water elements and find that connection to nature. Imagine a scene with no traffic, no news, no pollution, no civilisation. Just wind and water – plenty of that! A scene where you can gaze for hours to the millions of stars above you; enjoy the dozens of dolphins sliding through the water at the bow of the boat; admire the pink-orange-red sunrises and sunsets, without any airplane trails changing the fluffy and cauliflower-like cloud patterns.

By being disconnected from everything but nature, you’ll learn a great deal about the ocean. When you see the good, bad and ugly with your own eyes, talk face-to-face with people living on and for the ocean, and experience its value, it makes you eager to learn more, do more, be more, and likely Live more: At sea.

You’ll become very aware of the natural world around you. This inspires. And it’s eye-opening. You come to realise how disconnected from nature we are in our daily lives. In the middle of nature, far away from civilisation, you will see human impact. Usually we’re far away. It’s hard to make it tangible. It doesn’t really affect us. Or so we think. But by being out there, you literally broaden your horizon. Experience will make you think, gain fresh perspectives, and may inspire you to act to turn the tide of the ocean challenges.

We share tips & tools, helping accelerate personal journeys to alternative adventurous conscious life on or near the sea.

Ocean nomads adventures are not just a one time thing you join for a week or two and that’s it. These are experiences that change the way you approach life, nature and the ocean. We believe our trips are just the beginning for plotting the next course in your life. By jumping on board this, you also join our expanding global network of impact-driven travellers, ocean entrepreneurs, sailors, (free)divers, surfers, and active salty souls passionate about the ocean and eager to do good. On our community HUB we continue the conversation, action, team-ups and meet-ups beyond our events and expeditions to maximize the impact, fun, and ripple effects for ocean adventure and action. We got your back before and after the trip.

We used to have an image in our head that sailing is only for rich people, that it’s about showing off boats and boat toys, and that as crew you’re just meant to scrub the deck. Not true. Sailors are free spirits and ocean-minded people. Most of us share the same dream to live a simple life on a sailboat, set off to explore the world, and live life on their own terms. We unite and exchanges ideas to make this dream happen! We  connect with fellow nomads that are on the same mission. Who knows who you may meet during these adventures and what opportunities may come from it?

ocean Sports

Sailing Vessel Twister is a ship of +100 years that still sails the oceans, safely! Isn’t that amazing in itself? No plastic push buttons or winches on this vessel.

 She’s beautiful. She’s solid. She’s big. She’s spacious. She’s super comfortable. She’s got soul. She lasts. She has proven her worth and seaworthiness. 

Sailing ship Twister is a schooner built in 1902, with an impressive story to tell. Originally a fishing boat built out of wood, fifty-five years later, her wooden hull was replaced for a steel one so she could continue to fish. She now features all safety equipment, modern comforts, and all licenses and certificates to take you safely offshore. She sails under the highly regarded Dutch flag.

Her current owners are driven to sail her far, and with purpose. The aim is to facilitate memorable expeditions that people will treasure for life, and contribute towards a better planet.

Last season she we sailed with her offshore, conditions ranging between champagne sailing and 9 Beaufort, totalling 5000 NM. The only thing we broke were two plates. Given the success of last expedition we now go all in and all around the Atlantic!

The size of the ship allows us to bring more people together in a place. Through Twister we can have you experience international sailing as safely as possible. Twister focuses on safety and seamanship competence. Ocean Nomads on the community, content, and organization. Many certificates are obtained and complied with to pass the safety checks and requirements. This comes with a cost but the rewards are priceless.  Teaming up with Twister allows us to combine professionalism, safety, and adventure, impact and community facilitation.   

About the VEssel

Home port : Harlingen, Holland

Year built : 1902

Displacement : 88 tonnes

Length overall : 36m/118′

Draft : 2.8m/9’2″ Beam : 6.2m/20’3″ Rig : Schooner

Sail area : 332.5m/1090’8″

Number of sails : 6

Engine : Mercedes Benz 300 PK

Total number of berths : 22

Bathrooms : 2 A Tour of SV Twister:

A few more Benefits of jumping on board with us

Save lots of time and energy on researching boats, safety, captains & crew

We have sailed, worked, hitchhiked with +100 vessels by now. Teaming up with SV Twister is next level authenticity, safety, comfort  (think toilet buttons, your own comfortable bed, filtered water, not to mention space on board) and professionalism.  We’ve done our first succesfull collaboration with SV Twister last year (see the testimonials). This is sailing in style, hands-on, as safe as we can control. There are very few ocean worthy vessel like her out there taking people offshore (legally), and for this price.

More people, more fun, learning, and impact!

You can sail with 2,3, or 5 people. This is fun. We’ve done it. We’ve organized it. But going on an adventure with around 15 salt souls all as stoked about ocean sailing as you are is next level community living and socializing. Conversations and connections at sea go deeper in one day then in weeks on land. You’ll always find a few souls you get along with well.

SV Twister is 36 meter long. There is lots of space to move, stretch, work out, chill, relax. Below Deck, as well as on deck. There’s a steering hut for cold nights, a lounge room but playing games, reading, and chatting. And big table and space for communal dinner, music nights and other workshops we as a crew team facilitate spontaneous as we we navigate the seas. 

Especially for the longer voyages where dropping anchor is not a daily routine, this is priceless. We only have so much patience to sit back and relax, which is kind of mandatory in small vessels,where space is limited.

”   This was one of the most epic experiences of my life so far, and I can tell it is just the beginning.  The ocean has taught me so many lessons…to embrace all experiences (even seasickness), not worry so much, and just be in the moment. Two weeks without connection to the outside world was absolutely glorious. I feel reset. After a very fragmented life the past few years, being around a crew of 17 people every day was amazing…to interact naturally with each other, feel a part of a family of diverse ages, nationalities and backgrounds…I learned so much from these amazing humans. My heart feels so full.” – Sael

Summary! WHY JOIN?  

  • Meet your tribe and expand your sailing and ocean people network. Meet a beautiful bunch of adventurous unconventional dream chasers on a mission. Finding a boat is easy, finding a like-minded happy positive vibed team is what makes all the difference. The skills, stories, smiles, and contribution of your fellow curated crew, is what makes the trip like nothing else out there.
  • Around 15 fellow crew members to learn from and share with. Not just a few. 
  • Memorable and impactful moments. The good, the bad, the ugly. From wildlife sightings and sunrise at sea, to cooking up a meal on an angle and spotting plastic at sea. 
  • Connection to nature. Sailing the ocean is digital detoxing at its best. 
  • Discover Freediving by a licensed AIDA instructor. + optional next courses on request
  • Discover Kitesurfing by a licensed IKO instructor. +  optional next courses on request
  • Experience arriving into a new country by sail!
  • Serious adventure sailing but as safe as we can make it! Mum will be happy.
  • Accelerate your personal journey to make the dreams happen. Turn your intentions into actions. Today.
  • Expand your worldview, generate fresh energy and insights. You’ll step away from it all and get a dose of fresh perspectives on the world, fellow Ocean Nomads, and yourself.
  • Learn about minimizing your environmental footprint and to share what you have learned. Practice new habits and make different lifestyle choices.
  • Find and explore and build connections and partnerships to accelerate those dream and impact projects.
  • Learn the basics of sailing, navigation, build miles and develop your sailing skills and experience. Hands-on and from other that sail the seas.
  • Continuous Support. We got your back before and after the trip by staying in touch and building on what we create on board on our member hub.
  • Make the adventure sailing dreams real faster and with long term impact and friendship.
  • To sail on a ship of more than 100 years old. It cannot get much more sustainable when it comes to travelling oceans. 

Who's Joining?

It’s the people who make the adventure. This is the main message Suzanne learned after having sailed 30.000 miles on +50 different boats. We carefully curate a diverse, multi-skilled crew who share a similar mindset, to create a powerful team mix. It makes the difference.

We live beyond the status quo or desire to do so. We care for the planet. Minimize, simplify and cut down on our environmental footprint where we can. We lift each other up and support each other when in need.

a group of people sitting at a table on a boat.

OCEAN NOMADS EXPEDITION LEADER 

Every leg an Ocean Nomads expedition leader will be on board, representing the Ocean Nomads values and to make sure you get the most out of this trip. Most of them are Trip Alumni who previously joined and never returned. Now shining their light and experience on the journey! Maybe it’ll be you next trip. 

a group of people standing on the deck of a sailboat.

Professional Crew

Twister is managed by a professional crew including a captain, first mate and one or two deckhands. This is required by law on a vessel this size. You’ll be in safe, qualified and experienced hands. This doesn’t mean you only sit back and relax. This is a hands-on voyage involving everyone in sailing, operation, and watchkeeping of the ship.

a woman sitting on the bow of a sailboat.

Adventurer & explorer

Alternative lifestyle seeker

Striving to do good

Excited to share skills and stories

Eager to learn, share and care

Hands-on mindset

Saying Hell Yeah that’s me when reading more about our community

Your Caribbean ON Expedition Leaders

Suzanne van der veeken.

Ocean Nomad, Adventurer, Captain & Freedive Instructor

Hi! My name is Suzanne and I’m super excited to sail across the Atlantic and Caribbean with YOU, Ocean Nomads! A little about me. Half my time on this planet, I’ve been living a nomadic ocean minded lifestyle, navigating ocean and coastlines by sail, van, surf and mermaid fins. I hitchhiked 30.000 miles on sailboats and now slow travel coastlines living in my van. I wrote the Atlantic ocean travel guide Ocean Nomad and founder of the Ocean Nomads community. The mission: Connecting you to ocean, and to cultivate and encourage a simple, natural, conscious way of life. I’ve spent some winters in the Caribbean before, and I can’t wait to share this magic with you! I’ll be happily introducing you to all I have learned in those +15 years on nomad life, introducing you to freediving, boathitchhiking and more.

a woman holding a coconut on a boat.

Brianna Brady

Ocean Nomad, Live Aboard & Realizer of the dreams!

According to my mom, I swam before I could walk… I will take her word for it.  I just spent my first winter outside the USA surfing, sailing, RVing, hiking/hitchhiking, and connecting with other Nomads along the way and I AM NEVER LOOKING BACK.

My main goal as Community Co-Captain is to connect fellow nomads and help facilitate opportunities in all things sailing, environmental awareness, ocean sports and adventure, the way others have helped me.

Brianna is Ocean Nomads Community Captain and will be welcoming you in Martinique – Dominica – Guadeloupe.

a woman is riding a boat with a peace sign on her face.

Jonatan Bjorkman

Advanced Hitchhiker, Long Distance Hiker, Full time Vanlifer, Banana Pancake Professional

Hello fellow nature vagabonds! I couldn’t be more excited to partaken in such a great adventure and life experience on a sailboat with a great bunch of you ON.

My name is Jonatan and I’m from an island in Sweden. Travelling and being on the road without knowing what tomorrow brings has been in my DNA most likely since birth. Still don’t know from whom but things like cultural exchange, hitchhiking, vanlife, hiking, diving, skiing, kitesurfing, freedive, surfing to name a few has brought me to the most wonderful places and meetings in my life. And it’s just the meetings and the sharing thru life story’s that has been the most memorable thing. We know that Caribbean going to be amazing but I together with you will create wonderful memories together.

a man standing on the deck of a sailboat.

“The things I like the most about trips with Ocean Nomads is the mix of different nationalities, ages and levels of experience. With these trips, there’s always a general plan but also plenty of opportunity for spontaneity to have a real adventure!” – Louise Agren Croatia 2019 & Madeira-Canary Islands 20 21

Discounts & Memberperks

Now is the time.

Ocean Nomads members   receive 10 percent discount on the Expedition Investment.

An extra 5 percent discount applies when joining 2 Legs An extra 10 percent discount applies when joining 3 or more Legs.

We create some scholarship opportunities for limited budget determined ocean explorers. 

In collaboration with this ship and the costs that come with it we  can’t do a full exchange but we can do discounted prices with skill shares and trades. We love to hear what you have in mind via the Scholarship form.

Ocean Nomads Trips have always sold out. We have limited spots. Now is the time.

Not a member yet? Join the network now to have priority access to application handling and to claim your 10 percent trip discount this august.

ocean nomads adventure impact community logo.

Are you ready to be part of THE EXPEDITION crew?

We’d love that. Be aware. Especially the offshore sailing trips are not for the faint hearted. These can be serious ocean adventures and we want to be sure you’re ready and confident to join. 

The biggest value is in having a crew mix on board with similar mindsets and missions but different background and stories. We don’t just accept any booking to fill up a boat. Apply to join so we can learn more about you and make sure we’re all on the same page, and have a happy, safe, and meaningful experience accordingly. 

Questions? Explore the Frequently Asked Questions!

What does previous ocean nomads crew say.

Still smiling at the memories! Met – and still talking to – some lovely people. Refreshed my nautical skills (helming, navigation, astro identification, etc.) Shared some great experiences through conversation, music, stories, yoga, cooking together, seeing ocean wildlife, and so much more!

a silhouette of a man looking at the ocean at sunset.

Expedition ON '21

"The experience on twister with other Ocean Nomads was just really beautiful and I felt connected for the first time in decades, I felt part of a community and had companionship. I was so happy that it’s so all inclusive of gender race religion nationality and most importantly age. It has connected me with like-minded people of all ages and being very transformational personally because my life has been incredibly isolated as a single parent Who works from home. I can honestly say October and November I felt happy and free for the first time in maybe 22 years.  It gave me everything I was looking for. It has opened up so many possibilities to meet new people with similar vibes, including connection, companionship, purpose and being one with nature." 

a woman sitting on a boat reading a book.

“In my opinion Ocean Nomads sailing adventure are: 1. A reward for the senses by discovering incredibly beautiful places and breathtaking sceneries. 2. An unbeatable way to get introduced into the nice world of sailing, 3. An open window to learn watching our world and the people from another more conscious perspective. I see Suzanne as an inspirational person who, with her example, inspire others with ideas and proposals to define or redefine life projects and use inner energy for more noble purposes. Our oceans need strong committed people like her to advocate for our natural resources and leave them intact for the generations to come.” 

an aerial view of a boat with dolphins in the water.

Jose Maria Perez

Sicily 2018

"The sailing with such a beautiful ship. It is absolutely breathtaking to sail a tall ship and minimize the use of the motor as much as possible.

I joined the Twister Expedition to share my knowledge as a marine scientist studying cetaceans. I look at the sea a little differently than most sailors do, so it is beautiful to be able to share this knowledge and viewpoint since I believe science is not only for scientists.

There are many things that sailors and Ocean Nomads can do to help as citizen scientists.

Small tasks such as collecting data on cetaceans (Whales and Dolphins) on a sail can have a large impact in the management and conservation of species. 

Expedition ON 2021

"It’s amazing how many awesome friends you can make, and how much just one week on an ON trip can change your life"

Canary Islands '19

“Good sailing experience that makes me feel more confident on open seas. Made good connections to nice people and got valuable insights for my master plan.”  

a man is standing on the deck of a boat.

This was one of the most epic experiences of my life so far, and I can tell it is just the beginning.  The ocean has taught me so many lessons…to embrace all experiences (even seasickness), not worry so much, and just be in the moment. Two weeks without connection to the outside world was absolutely glorious. I feel reset. After a very fragmented life the past few years, being around a crew of 17 people every day was amazing…to interact naturally with each other, feel a part of a family of diverse ages, nationalities and backgrounds…I learned so much from these amazing humans. My heart feels so full.” 

a young woman climbing the mast of a tall ship.

Galicia '21

The most unforgettable week. The trip preparation and the crew members turned what would otherwise be an adventure into something a bit more special. I took part in two ocean nomads trips so far. To say it was life changing sounds dramatic but it really was. Being able to share time and experiences with people with different backgrounds but of a similar mindset was incredible. I like to think that I can have and help contribute to a similar experience for myself and others as a member of the Flotilla crew.” 

a group of dolphins swimming in the water.

Ben Clipstone

ON Lanzarote & Galicia

“The things I like the most about trips with Ocean Nomads is the mix of different nationalities, ages and levels of experience. With these trips, there’s always a general plan but also plenty of opportunity for spontaneity to have a real adventure!”

a woman reading a book on a boat.

Louise Agren

Croatia 2019 & Madeira-Canary Islands 2021

Connect with trip alumni & other ocean adventurers on our member network

“During my interview call with Suzanne for ExpeditionON with Twister last summer, I immediately knew I wanted to join the Ocean Nomads network and sailing adventure. Her energy and values were exactly what I was looking for and I could NOT wait to get onboard and meet everyone. As soon as I hung up the phone I thought to myself “This trip is going to change my life”…. and it sure did. So I packed up my life into a duffle bag a few months later, boarded Twister in Madeira and set sail towards The Canary Islands.  Long story short, after I hopped on Twister and sailed off into the sunset, I was surrounded by amazing people and had the complete feeling of freedom I had hoped for. With little convincing from fellow ON members during one of the monthly meetups, I also decided to take their advice and spend the winter in the canaries. This included…renting a caravan with fellow Nomad Cay, sailing on Bluepearl with Captain Wolfgang , Thomas, Robert, Kyra, and meeting Jacky, Eoin, Luca, Sael and of course Suzanne. My lifelong dream has been to spend time outside of the US, explore different places, meet , new people and just live somewhere different than what I grew up with. If you told me this time last year that I would have spent the better part the last 365 days sailing around The Canary Islands,surfing in Ireland, sleeping in a van ALONE in England and writing this newsletter on an island in the Adriatic Sea, I would have rolled my eyes at you.  But after joining Ocean Nomads a little over a year ago my life has done a complete 180° ( in the best way possible) and I have the network and so many of you to thank for that! – Brianna

Connect to Nature

Most of us spend more time indoors than outdoors. It’s easy to forget the natural world we’re coming from and living in. On the ocean, you face the wind and water elements and find that connection to nature. Imagine a scene with no traffic, no news, no pollution, no civilisation. Just wind and water – plenty of that! A scene where you can gaze for hours to the millions of stars above you; enjoy the dozens of dolphins sliding through the water at the bow of the boat; admire the pink-orange-red sunrises and sunsets, without any airplane trails changing the fluffy and cauliflower-like cloud patterns.

We like for you to see for yourself how beautiful the ocean are!  And hopefully ignite the supersupower within you to take steps into a conscious nomadic life in or near the sea.

A connected, conscious community is key to accelerating positive change. Through community, we can harness our collective passion for the ocean into solutions for a healthier ocean. 

Ocean nomads sailing crew adventure logo.

We are a global vagabonding community of impact-driven travellers, sailors, (free)diver, surfers, and active salty souls passionate about the ocean and driven to not settle for anything less we’re capable of living and contributing.

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Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade wind and the pleasant waters are ideal for a sailing vacation, not to mention the fact that navigating amongst the many islands here is quite exciting. The ports and islands in the Caribbean are ideal for those who love adventures, beautiful sights, and hotness.

Read more information about sailboat charter in the Caribbean on the following tabs: About Caribbean , Caribbean weather . Get some inspiration from the Caribbean itineraries tab and start planning your next sailing itinerary, read detailed descriptions of Caribbean sailing destinations , or Caribbean sailing articles.

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Location of the Caribbean

The phrase, Caribbean region, stands for the North and Central American groups of islands. In a broader sense, some Central and South American countries also belong here, such as Columbia or Venezuela. There are more than 700 islands in the region. We can divide the Caribbean Islands into three main parts. The Bahamas, the Greater Antilles, and the Lesser Antilles.

Beaches in the Caribbean

There are several gorgeous beaches, gulfs, and lagoons here. The crystal clear seawater and warm sunlight create a picturesque view. The beauty of the landscape will surely make your travel memorable. The white sandy shores of the Caribbean Sea are among the most astonishing swimming sites in the world. Here are some:

Gulf of Maundays, Anguilla

One of the most popular holiday resorts, Cap Julica is in this gulf. The amazing five-star resort provides full comfort and luxury. Thus, no wonder celebrities also like staying here. The beach has a private bar and other services as well.

Valley Church, Antigua

A cosy beach that enchants visitors with different shades of blue water. The water is calm and crystal clear, white sand carpet covers its shore. You can discover hundreds of other beaches between Antigua and Barbuda. They will certainly outshine your expectations. The secret gems of this area are its hidden gulfs, which you too can explore if you rent a boat.

Pink Sands beach

Many visit Harbour Island to view this famous section of the seaside. The coral is a unique mixture of broken shells, miniature stones, and calcium carbonate. It colours the sand with pink fragments. It’s a wide and long beach surrounded by calm water. It can be an ideal and beautiful venue for wedding ceremonies, sports, or yoga.

Treasure Beach, Bahamas

It’s among the best beaches in the world. Treasure beach is a 3, 5- mile -long section of the shore with every service available to make a vacation incomparable and even more excellent. You can enjoy pleasant cafés and restaurants or try watersports.

Main attractions in the Caribbean

The picturesque scenery welcomes visitors with several colourful and unique programs. Besides beautiful beaches, you can take pleasure in viewing the exotic flora of the jungle or the underwater wildlife. Sea turtles are amazing residents of the Caribbean Sea. They are one of the endangered species, thus, numerous rescue and breeding programs started in the past few years to protect the animals. Many visitors come to Puerto Rico to see the turtles, while they’re laying their eggs in the sand. They also come to see the exciting moment, when the little turtles leave their nests and go into the water. Besides water and seaside sights the Caribbean region also has a rich cultural heritage. There are more than 40 museums in Cuba, that display art, music, the revolution, chocolate, or cigars.

The Caribbean weather

The Caribbean region has the traits of all year hot and humid tropical climate. The weather is somewhat cool and dry from the middle of January to the middle of April. From the middle of June to the middle of November it’s usually hot, wet, and rainy. Subtropical monsoon climate dominates in the region. The average yearly temperature is 28 °C.

Sailboat charter in the Caribbean

A roundtrip on the Caribbean Sea could be a very exciting and memorable program for the whole family. Rent a small boat, a luxury yacht, or a sailboat. It’s important that you find out about landing places. The Caribbean region involves numerous ports, small and large. However, they might be very different. The most popular and high-standard ports are in the larger cities. These are the ports of for example Nassau, Falmouth, Puerto Rico, Philipsburg, or Mexico. They are well-equipped and provide all the services necessary for boating. The majority of sea centers and smaller islands are in daily connection.

The most popular ports in the Bahamas

Great guana cay.

Great Guana Cay is located in the centre of the Exumas. It has two great anchorages: Black Point and Little Bay. Black Point is a true gem with a nice port and several moorings. People are very friendly and casual, and they find it important to help sailors in any way they can. Little Bay is a small bay at the southern end of Black Point. The sea bottom is sandy, making it ideal for securing our boat safely. The depth of water is app. 3-4 metres. There is a beautiful beach here, but there are no establishments, ports or shops. Information about Exumas sailing or boat rental in Exumas

Spanish Wells

Spanish Wells is located on St. Georges Cay, west of the northern corner of Eleuthera. Its port is constituted by a long channel bordered by two small islands. It is protected well and is only open for the winds coming from the eastern direction. There is a great port and a hurricane hole in the west where boats are tied to mangrove trees. There are six anchoring buoys on the eastern side. We can find Spanish Wells Yacht Haven & Marina here which is a full-service yacht marina with 40 berths; besides the basic services, they also have a bicycle rental.

The downtown is within walking distance. We can anchor at Royal Island Harbour in the west, which provides ideal anchorages for vessels with a larger draft. The only disadvantage is that they have no amenities or services. Information about Eleuthera sailing , or boat rental in EleutheraMore about Bahamas sailing tours, or Bahamas yacht rental

The most popular ports in the BVI

Nanny Cay is located on the southern coast of Tortola. It is located a little over 3 kilometres from Burt Point. At this port, we have the opportunity to pull our boat from the water, among other services. Nanny Cay Marina offers 320 berths; 120 on the outer parts and 200 in the inside. They provide access to fuel and electricity in both areas. We need to pass through a narrow route for entry.

Road Harbour

Road Town is the capital of Tortola and the sailing centre of the British Virgin Islands. We can enter the port through the Sir Francis Drake Channel . Road Harbour has several yacht marinas providing full service and accommodation. We can find Road Reef Marina, Fort Burt and Wickham’s Cay I and II here; Road Reef Marina and Fort Burt are on the western side, while Wickham’s Cay is on the north. There are over 120 berths and downtown Road Town can be found nearby. Many sailors start their trip here when visiting the British Virgin Islands. Information about sailing in Tortola , or boat hire in Tortola

Virgin Gorda Yacht Harbor és St. Thomas Bay

The Virgin Gorda Yacht Harbor is in St. Thomas Bay. It is easy to approach it, we only have to sail the marked channel. The harbour is beautiful, offering great services and marine gas. There are 100 berths, and it is possible to stay for only a few hours, a day, or long-term as well. It is close to the centre of Spanish Town. It is a very peaceful town where you can find many shops, restaurants, and bars. One of the most famous attractions of the town, The Baths, is about 3 km from here. This is a collection of granite rocks on the beach that have become large rock formations. The rocks from tidal basins, channels, and spectacular caves open to the surrounding waters. Information about Virgin Gorda sailing , or Virgin Gorda boat chartersMore about BVI sailing routes , or BVI boat rental

The biggest ports in Puerto Rico

San juan cruise port.

With two terminals, San Cruise Port is one of the largest and busiest ports in the Caribbean. The two terminals can accommodate up to 9 cruise ships at the same time. Due to its geographical location, the port is safe even during hurricane season. The port offers several services like towing, drinking water access and electricity, telecommunication services and shops. The city’s tourist attractions are easily accessible by public transport.

Marina Puerto Chico ( Fajardo )

The marina of Fajardo is located on the east coast of Puerto Rico. It is a natural, quiet coast, and the depth of the water is 5-6 m. Despite its small size, it has a great infrastructure: water, electricity and refuelling are available. You can easily visit Culebra, Vieques and the British Virgin Islands from here.

Port of Mayagüez

The third busiest port in Puerto Rico is northwest of downtown Mayagüez, stretching for 6 km along the coast. The depth of the water is 8-9 m. Despite being one of the smaller ports, it can accommodate boats up to 150 m in length. The communication infrastructure is also outstanding. More about Puerto Rico sailing, or boat rental in Puerto Rico

The most popular ports in Mexico

La Paz is the most city in southern Mexico on the Baja California Península. It has several ports.. One of the best-equipped ports is Marina Cortez, located in the heart of the bay. It offers a number of exclusive services for even the largest sea yachts.

The city’s port, called El Cid, is way more than a simple landing opportunity. There is a bustling market and several miles of nearby beaches with golden sand. The local dive shop is excellent, you can get all the necessary equipment here. In the port area, you will find plenty of high-quality accommodation opportunities. More about Mexico sailing , or boat rental in Mexico

The biggest ports in Cuba

Port of cienfuegos.

The main port in the southern part of the island is La Perla del Sur or the Pearl of the South. The port of Cienfuegos is considered a large port in Cuba. It can accommodate boats up to 150 m. The depth of the seabed is 12 m. While Christopher Columbus visited in 1494, it was formally founded in 1819.

Port of Santiago de Cuba

The second-largest port city of Cuba is located in the southeastern part of the island, in Oriente Province. It is a major port for import and export in the region. The bay is quiet and protected against winds. The famous Casa del Habano is a few-minute walk from the port. Here, you can buy the best-quality Cuban cigars and you can visit the Bacardi Museum. More about Cuba sailing, or boat rental in Cuba . Another option is to explore the sea by yourself on the deck of a yacht charter. If your only wish is an amazing sea vacation, or the presence of stunning natural wonders, visit the Caribbean Sea to find all of these.Find sailing routes in the Caribbean .

More information about the Caribbean

Sail in Caribbean

Caribbean sailing routes & Caribbean sailing destinations Sailing destinations & Sailing routes

Sailing in the Caribbean: an unforgettable experience for you. Caribbean sailing trips

Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade [...]

For more precise information about the Caribbean area,  please narrow down your search. It is necessary in this case, because of geographic diversity and the large scope of the area. First select a destination on the sailboat charter in the Caribbean tab and choose the Weather tab of the selected area and read the related description.

Rent a sailboat in the Caribbean, and cruise around the Caribbean

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When to Sail the Caribbean

When to Sail the Caribbean | Life of Sailing

Last Updated by

Daniel Wade

June 15, 2022

The best time to sail the Caribbean is during the beginning and end of summer when the weather is warm, and conditions are stable.

The Caribbean is an extremely popular offshore sailing location, as conditions are usually manageable and accommodations are affordable. Most sailors spend time in the Caribbean during the summer, though it's best to avoid peak hurricane season.

Table of contents

Why Sail the Caribbean?

It's easy to see why the Caribbean is a dream sailing destination for so many people. The region is dotted with islands, coral reefs, crystal clear blue water, and fair weather most of the time.

During the summer, temperatures in the region are high, and winds blow reliably. Thunderstorms and other hazards occur in the area, but the conditions in the Caribbean are usually fair. This is especially along well-known recreational sailing routes.

The area is extensively mapped, and there's a wealth of experience online and in the Southeast U.S. on where to go and when to go. Sailors are likely to encounter numerous other vessels, many of which are U.S.-flagged recreational craft.

Sailing Hazards in the Caribbean

The Caribbean is not without its hazards, especially when it comes to sailing. Generally, conditions are fair and relatively reliable in this tropical climate. However, that can change quickly and turn into a serious problem for sailing vessels.

Thunderstorms

Thunderstorms are always a hazard in the Caribbean, and this is especially true during the summer. It just so happens that the summer is also the best time to sail the Caribbean , so it's important to watch out for them.

Caribbean thunderstorms are usually intense but short-lived. Conditions inside a thunderstorm include momentarily elevated waves, high gusty winds, rain, hail, and lightning. It's best to avoid thunderstorms if possible (sail around them if they're far away), but many sailors encounter these conditions.

Hurricanes are many times more hazardous to sailors than typical Caribbean thunderstorms. These monster storms are often hundreds of miles wide and contain sustained winds, sometimes in excess of 100 knots or more.

Thankfully, hurricanes are well-studied and don't just spontaneously appear in the late afternoon. Advanced warning is usually available, so it's best to stay tuned into weather radio and avoid areas where hurricane development is possible.

How to Learn More about Caribbean Weather

The climatology of the Caribbean is well-studied, and there's a wealth of information available for mariners on the subject. If you want to read into it, check out online information and sailing guides to tropical cyclones and summer sailing hazards in the Caribbean region.

Best Months to Sail the Caribbean

The primary consideration when choosing the best summer months to sail the Caribbean is the weather. It's best to choose months where weather conditions generally don't encourage the development of severe thunderstorms and hurricanes.

May is the safest warm month to sail around the Caribbean. During this period, thunderstorm development is rare, and hurricanes are practically non-existent. This changes slightly from year to year, but overall, May is the best month to sail around the Caribbean.

On average, June is one of the safest months to sail around the Caribbean as hurricanes are extremely rare and thunderstorms aren't particularly common. In fact, June has the least amount of summer storms in the Caribbean.

July is a close runner-up to June for Caribbean sailing, as July storms are infrequent, and hurricanes are also rare. However, hurricanes have occurred in the Caribbean during July, so you'll need to be more vigilant.

That said, July is still a pretty good option for trips around the Caribbean. Tourism spots are open and flourishing during this time, and lots of boats are also out. This means it's an ideal time to meet people and enjoy exploration with other boats.

August starts out much like July in the Caribbean, but the month is meteorologically active, and storms are much more common. Over the course of August, the storm and hurricane threat in the region nearly doubles, and weather patterns become more unpredictable.

September is the peak month for severe weather in the Caribbean, and sailors must be cautious when sailing in the region. During the beginning and middle of the month, explosive thunderstorm development is common, and the weather can be severe. 

That's not to say that you can't sail in the Caribbean during September. Many people do, citing the warm temperatures. It means that the risk of encountering dangerous storms and rapidly-changing weather conditions is much higher during the month.

October through December

October, November, and December are still generally warm months in the Caribbean, but they're also a very active time for severe thunderstorms and hurricanes.

Compared to May and June, these three months are generally not the best times to sail the Caribbean. There is very little benefit and a significantly heightened risk of encountering severe weather.

Planning a Caribbean Sailing Trip

Planning is one of the most important things to do before embarking on a voyage in the Caribbean. The first step in planning is to choose the best time to go, which we've covered in this article already. After choosing what time is best for you, it's time to prepare your boat and make a plan.

Preparing your Sailboat for the Caribbean

The first thing to do when preparing your boat to sail is to inspect its current condition and make all the necessary repairs. Consider the bare essentials of sailing, then consider the potential hazards you're likely to encounter in the region.

The Caribbean is hot and tropical, so be sure to choose your clothing and provisions accordingly. Wool socks probably aren't as important as wet weather gear, for example, as you're much more likely to get drenched by days of rain than to freeze in sub-zero temperatures.

Check your rigging, make sure your sails are in good condition and have the bottom of your boat scraped and painted with red lead or another anti-growth paint. Barnacle and marine life grow rapidly in the Caribbean, so it's vital to have the bottom scraped and prepped for the environment. 

Also, be sure to flush all water systems prior to leaving. The Caribbean is home to sensitive marine environments, and your exhaust and drain systems could harbor harmful invasive species from your home waters.

Finally, take your sailboat on a shakedown cruise, preferably during rougher conditions, to refresh your skills and test your rigging. A shakedown cruise will help you weed out any hidden issues that you might have otherwise overlooked.

Don't forget to stock plenty of provisions, especially if you intend to visit a foreign country. Food, medication, and other essential supplies may not be widely available, especially in the small island nations that Caribbean sailing tourists tend to frequent.

Laws and Declarations

If you plan on staying abroad, be sure to check local laws and contact a reputable marina before departure. Make arrangements with the marina to ensure that you know what to do and what to declare to authorities before you arrive.

Remember, the borders of the country begin the moment you cross from international water into territorial or national waters. According to the 1982 United Nations Convention on the Law of the Sea, international waters begin and end 12 miles from the coastline of a country.

Finally, be sure to check the weather before and during your voyage. Due to the tropical climate of the region, weather can change on a dime and cause problems for you and your vessel. 

If you plan your trip around broader forecasts and stay tuned throughout, you should have a safe and pleasant time sailing around the Caribbean.

You can receive regular weather updates via satellite, which is a good way to supplement the internet and VHF radio. Satellite weather forecasts are particularly important in areas without accurate (or any) local weather forecasts. Additionally, a wind vane and a barometer are also great to have.

Related Articles

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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The boat is its age but it is well maintained and repaired by someone who knows their stuff. Completely comfortable for a stay in a small group, we really enjoyed discovering Guadeloupe on board. Marc was very available and gave good advice before and during the cruise.

We had a fantastic time. Mathias is a very gracious host. The Jeanneau Sun Fast 32 is very fun to sail, well equipped, and functions well as a live-aboard for a week. Mathias was always available for questions or concerns. And our vacation went off without a hitch. Thank you so much for such an incredible and unforgettable experience!

Charter a sailboat in the Caribbean with or without a skipper with SamBoat

The Caribbean is a region in the Americas. It has more than fifty islands that belong to different countries such as Cuba, Dominican Republic, The Bahamas, Grenada, etc. The Caribbean is a highly visited place for its beauty and great climate. The best time to visit the Caribbean is from December to May, during these months the intensity of the heat decreases and the sun's rays are not as strong. However, it is the high season, so the prices increase. We advise you to plan well your visit to anticipate your expenses.

Many travellers who have visited the Caribbean say that there is no better way to discover its wonders than onboard a boat. Charter a sailboat to explore the islands of the region or rent a catamaran in the Caribbean to relax in the Sea. Whichever option you choose, you will enjoy an unforgettable experience. On SamBoat's website, you will find several destinations that offer affordable sailboats all year round. Don't miss the opportunity to enjoy the Caribbean uniquely.

Sailboat rental in the Caribbean

By renting a sailboat in the Caribbean, you have the chance to visit several islands to enjoy their beauty. Here are the best destinations for sailing in the Caribbean:

Punta Cana: has calm beaches, crystal clear waters and calm waves. It has several places to anchor your boat, most of them with sandy beaches.

Cuba: has more than twenty cays that can only be visited by boat. Don't miss the opportunity to sail in Cuba and enjoy its peacefulness.

Barbados: an island with a calm sea ideal for sailing in the western part of the island and perfect waves for surfers in the southeast. Visit Crane Beach, famous for its pink sand.

How much does it cost to rent a sailboat in the Caribbean?

The price for yacht charter in the Caribbean varies depending on the season and the country you want to rent a vessel. Below are listed some of the prices:

Puerto Rico, around 300 euros per day

The British Virgin Islands, 270 euros per day

Cuba, 250 euros per day

Martinique, 180 euros per day

St Lucia, 300 euros per day

The Bahamas, 350 euros per day

Guadeloupe, 180 euros per day

Please note that prices may increase during the high season. If you want to rent a catamaran during the high season, we recommend you to look two months in advance and start the rental process as soon as possible.

Do you need a license to rent a sailboat in the Caribbean?

Renting a sailboat in the Caribbean is a unique experience. When renting a sailboat, you should consider the regulations of the countries that are in the Caribbean.

If you want to rent a sailboat in St Barths, the Dominican Republic, Puerto Rico or Grenada, you do not need a licence, but you need to prove your sailing experience. To prove your sailing experience, we suggest that you have a nautical curriculum demonstrating your previous experience.

If you don't have a license or experience, you can rent any other boat from our catalogue with a skipper. Skippers are helpful, they can show you places that only locals know. Rent a boat in the Caribbean with SamBoat.

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Living On A Sailboat In The Caribbean

In my years of sailing, I’ve had the opportunity to live on a sailboat in some of the most beautiful places on earth – including the Caribbean.

There’s something special about living on a boat in this part of the world. Maybe it’s the turquoise waters, the white sand beaches, or the friendly locals. Whatever it is, I can’t get enough of it!

If you’re thinking about making the jump to liveaboard life in the Caribbean, here’s what you need to know…

How Much Does It Cost To Live On A Sailboat In The Caribbean?

What does it cost to live on a sailboat in the Caribbean? It’s a question I get asked a lot, and it’s not an easy one to answer. There are so many variables, from the size and type of boat you live on, to the location you choose, to the lifestyle you lead.

That said, I can give you some ballpark figures based on my own experience living on a sailboat in the Caribbean for over 10 years. Keep in mind that these are just estimates, and your own costs may be higher or lower depending on your situation.

The biggest variable in the cost of living on a sailboat is the boat itself. If you own a boat, you’ll have to factor in the cost of maintaining and repairing it. If you’re chartering, you’ll need to budget for the cost of the charter itself.

Assuming you have a boat and are living on it full-time, your other major costs will be food and fuel. Food costs will vary depending on how much you eat out, and whether you buy fresh or canned goods. Fuel costs will depend on how much you use your engine, and whether you use propane or diesel.

Other costs to consider include insurance, docking fees, and repairs.

Insurance is a must if you’re living on a sailboat in the Caribbean. Docking fees will vary depending on the marina you choose, and repairs can be expensive if you’re not handy with a wrench.

All told, you can expect to spend around $2000 per month if you’re living on a sailboat in the Caribbean. This is just a rough estimate, and your actual costs will vary depending on your situation.

Cost Of Living On A Sailboat In The Caribbean

Sailboats are often associated with luxury and a carefree lifestyle. But what is the cost of living on a sailboat in the Caribbean really like?

I spoke with Gary Jobson, world-renowned sailor and sailing analyst, about the cost of living on a sailboat in the Caribbean. Here’s what he had to say:

“The cost of living on a sailboat in the Caribbean can vary greatly depending on the size of the boat and the lifestyle you want to live. A small boat with a few creature comforts will cost less than a larger boat with all the bells and whistles. And, of course, your lifestyle will also dictate your costs.

“If you want to live a simple life, you can do so quite cheaply. But if you want to live a more luxurious lifestyle, it will cost more. It really all comes down to your personal preferences.”

So, there you have it! The cost of living on a sailboat in the Caribbean can vary greatly depending on your lifestyle and the size of your boat. But no matter what your budget is, you can find a way to enjoy the sailing lifestyle in the Caribbean.

Maintaining Your Boat

Assuming you have the boat in the water, you now have to maintain it. This includes painting the bottom, varnishing the bright work, replacing the zincs on the hull, and caring for the sails and canvas. You also have to keep the boat clean and free of mildew.

In the tropics, this is a full-time job. You have to wash the boat every day with fresh water to keep the salt from eating into the paint and gelcoat. You also have to make sure the bilges are dry and free of any stagnant water.

Marina or Mooring Costs

The cost of living on a sailboat in the Caribbean can be quite expensive, especially when it comes to Marina or Mooring fees. In some cases, these fees can be as high as $600 per month!

However, there are a few ways to help offset these costs. One way is to live aboard your boat at a marina that offers discounts for live-aboards. Another way is to join a sailing club which often have their own moorings or docks.

Of course, the best way to offset these costs is to simply sail your boat to a less expensive location. In many cases, you can find moorings for as little as $100 per month in the Caribbean.

So, if you’re looking to save money on your sailing lifestyle, be sure to keep an eye on your Marina or Mooring fees. With a little planning, you can easily offset these costs and keep your budget in check.

Food And Supplies

What does it cost to live on a sailboat in the Caribbean? It’s cheaper than you might think!

Here are some tips on food and supplies:

  • Shop around for the best prices on food and supplies.
  • Buy in bulk when possible.
  • Use coupons and discounts.
  • Shop at local markets for fresh produce.
  • Plan your meals ahead of time to save money.

With a little planning and effort, you can save money on food and supplies and enjoy a great lifestyle in the Caribbean!

What are the little luxuries that make living on a sailboat in the Caribbean so enjoyable? It could be the sound of the waves lapping against the hull of your boat at night, or the warmth of the sun on your face during the day.

Maybe it’s the feeling of being surrounded by natural beauty, or the sense of freedom that comes with being on the open sea.

Whatever it is that makes living on a sailboat in the Caribbean special, there’s no doubt that it comes at a cost. But for those who are willing to trade in the comforts of land for the adventure of a lifetime, the cost is well worth it.

Gas And Water

The cost of living on a sailboat in the Caribbean can be expensive, but it doesn’t have to be. One of the biggest expenses is gas and water.

Here are a few tips to help you save money on gas and water:

  • Use a water maker. A water maker will save you money on water by turning seawater into fresh water.
  • Use a holding tank. A holding tank will save you money on water by storing water that you don’t use right away.
  • Use a gas saver. A gas saver will save you money on gas by reducing the amount of fuel you use.
  • Use a wind generator. A wind generator will save you money on gas by generating electricity from the wind.
  • Use a solar panel. A solar panel will save you money on gas by generating electricity from the sun.

Can You Live On A Sailboat?

Sure, you can live on a sailboat in the Caribbean. But is it really living? I mean, you’re constantly having to worry about the weather, you’re always fixing something on the boat, and you’re never really sure where you’re going to be from one day to the next.

sailboat in the caribbean

Don’t get me wrong, I love sailing. It’s one of the most freeing and exhilarating experiences you can have. But it’s not for everyone. Some people just can’t handle the constant uncertainty and the lack of creature comforts.

So, if you’re thinking about living on a sailboat in the Caribbean, ask yourself this: can you handle being constantly on the move, always having to be prepared for the worst, and never really knowing what’s going to happen next? If you can, then go for it. It’s an experience you’ll never forget.

You May Learn To Sleep Lightly

You may learn to sleep lightly on a sailboat. The gentle rocking of the boat can lull you to sleep and the fresh air can help you to sleep soundly.

However, you may also find yourself wakeful in the middle of the night, listening to the creaking of the boat and the sound of the waves.

If you are wakeful, you may want to take a look around the boat to make sure everything is secure, or simply enjoy the peacefulness of the night.

How Do You Feel About The Heat?

The heat can be intense when sailing in the tropics. I once sailed from Antigua to St. Lucia in the middle of August. The temperature was in the low 90s with high humidity.

I was constantly wet from sweating and the boat was like an oven. I don’t mind the heat, but I know some sailors who do. They prefer to sail in cooler weather.

How Much Space Do You Need?

You might be surprised how little space you actually need to live on a sailboat. Of course, it depends on the size of the boat and how many people are living on it. But even a small sailboat can comfortably accommodate two people.

Of course, you won’t have the same amount of space as you would in a house or apartment. But that doesn’t mean you can’t live a comfortable life on a sailboat. There are plenty of people who do it successfully.

So, how much space do you need? It really depends on your lifestyle and what you’re used to. If you’re used to living in a small space, then you’ll probably be just fine living on a sailboat. But if you’re used to a more spacious lifestyle, then you might find it a bit more challenging.

Ultimately, it’s up to you to decide how much space you need. But don’t let the size of the boat deter you from living your dream. There are plenty of people who have done it successfully.

Why would you want to live on a sailboat?

Sailing is one of the most freeing and exhilarating experiences you can have. And what could be more freeing and exhilarating than living on a sailboat?

Sailboats are relatively inexpensive to maintain and operate. They offer a level of freedom and flexibility that other types of boats simply cannot match.

Plus, living on a sailboat in the Caribbean is about as close to paradise as you can get. The weather is perfect, the scenery is beautiful, and the people are friendly. What more could you ask for?

Why would you want to live in the Caribbean?

The Caribbean is a great place to live for a number of reasons. First, the weather is amazing. You can expect sunny skies and warm temperatures year-round.

Second, the Caribbean is a great place to relax and enjoy life. There are plenty of beaches to lounge on, and the laid-back lifestyle is perfect for those who want to escape the hustle and bustle of city life.

sailboat in the caribbean

Third, the Caribbean is a great place to sail. The trade winds make for perfect sailing conditions, and there are plenty of islands to explore.

And fourth, the people in the Caribbean are some of the friendliest you will ever meet. They are always ready to help out and make you feel welcome.

So, if you are looking for a place to call home, the Caribbean is a great option. It has everything you need to live a happy and healthy life.

What Are Some Things You Should Know About Sailing In The Caribbean?

  • The Caribbean is a great place to sail, with warm weather and beautiful scenery.
  • There are many different islands to explore, each with its own culture and attractions.
  • The sailing conditions can be challenging, with strong winds and currents.
  • There are also hurricanes and tropical storms to be aware of.
  • But overall, sailing in the Caribbean is an unforgettable experience.

Tips For Sustaining Yourself While Living/Working In The Caribbean

1. Find a balance between work and play: It’s easy to get caught up in the non-stop party atmosphere of the Caribbean, but it’s important to find a balance between work and play. Make sure to schedule some time each day to relax and enjoy the beautiful surroundings.

2. Get involved in the local community: One of the best ways to sustain yourself while living in the Caribbean is to get involved in the local community. There are many ways to do this, whether it’s volunteering, joining a local sports team, or simply getting to know your neighbors.

3. Be prepared for the unexpected: The Caribbean is known for its laid-back lifestyle, but that doesn’t mean that everything will always go according to plan. Be prepared for the occasional power outage or unexpected delay.

4. Learn to relax: One of the most important things to remember while living in the Caribbean is to relax. This is a different way of life, and it’s important to go with the flow. Don’t sweat the small stuff and enjoy the simple pleasures of life.

Is Living On A Sailboat Worth It?

Yes, living on a sailboat can be an incredibly rewarding experience. It allows you to live a lifestyle that is far removed from the hustle and bustle of everyday life on land.

You get to experience the beauty of the Caribbean islands and their people firsthand. And, of course, sailing is an amazing way to see the world.

Of course, there are also some challenges that come with living on a sailboat. It can be difficult to find safe anchorages and good weather can be hard to come by at times. But, overall, I think the pros outweigh the cons and living on a sailboat is definitely worth it.

How big of a sailboat do I need to live on?

Assuming you have no experience living on a boat, you’ll need a minimum of a 35-40 footer. This size will give you some room to move around and store things. If you plan to live on your boat long-term, you might want to consider a larger boat.

Do You Pay Taxes If You Live On A Boat?

The answer to this question depends on the country in which you reside. If you live in the United States, you are required to pay taxes on your income, regardless of whether it is earned on land or at sea.

However, if you live in a country with more relaxed tax laws, such as the Bahamas, you may not be required to pay taxes on your income from sailing.

What Are Disadvantages Of Sailing?

  • Sailing can be dangerous.
  • The weather can be unpredictable and severe storms can occur without warning.
  • Sailing can be expensive, especially if you own your own boat.
  • Sailing takes time and effort to learn how to do it properly.
  • You need to be physically fit to sail, as it can be demanding on your body.

Is Sailing An Expensive Hobby?

No, sailing is not an expensive hobby. In fact, it can be quite affordable. There are many ways to sail without spending a lot of money.

You can sail on a smaller boat, or you can charter a boat for a week or two. You can also join a sailing club, which will give you access to boats at a fraction of the cost of owning one.

Conclusion On Living On A Sailboat In The Caribbean

Living on a sailboat in the Caribbean is an amazing experience that I would recommend to anyone. The scenery is breathtaking, the people are friendly, and the sailing is some of the best in the world.

There are, of course, some challenges to living on a boat, but overall it is an incredibly rewarding experience. I’m so grateful to have had the opportunity to live on a sailboat in the Caribbean and I hope to do it again someday soon.

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Cost To Live On A Sailboat In The Caribbean

The Caribbean is a great place to sail to and just forget about all your worries. But how much does it cost to live on a sailboat in the Caribbean?

Michael Moris

March 16, 2023

This article may contain affiliate links where we earn a commission from qualifying purchases.

‍ The Caribbean is a great place to sail to and just forget about all your worries. But how much does it cost to live on a sailboat in the Caribbean?

Living on a sailboat in the Caribbean will cost you about $2,500 per month if you exclude the cost of buying a boat, which is around $25,000. You might have to get a marina slip for around $800 a month. Other expenses include taxes, food items, and water and gas bills.

Living on a boat is pretty much like living in a flat. Like an apartment, you'll most likely be investing in your boat's financing, taxes, maintenance, and essentials. We've created this detailed guide to help you determine how much it will cost to live on a sailboat in the Caribbean.

As people who have lived on sailboats for extended periods, we know exactly how much it costs. We'll share these insights with you to help you decide whether you're up for the adventure or whether the expenses are too much to bear.

sailboat in the caribbean

Table of Contents

‍ How Much Does it Cost to Live on a Sailboat in the Caribbean?

Getting a marina slip.

Living in the Caribbean isn't quite as expensive as most people think. A decent marina spot in the Caribbean may be acquired for  around $800 per month . This way, you get access to security, good facilities, as well as a convenient place to stay.

You could bring it down and get a marina slip near where residents will dock their yachts for less money; however, you won't get all the other perks and conveniences. It's also possible that you'll end up outside of town. To put that into perspective, if you stay a year in the Caribbean, you'll be paying $12,000 for the marina slip. It's less expensive than paying rent every month (especially if you live in a nice area), and it's a lot cheaper than planning a vacation.

You will discover that you can stretch your budget a lot farther if you opt to live in a few of the smaller, underdeveloped island countries. In this case, a  luxurious marina spot  can be rented for a few hundred dollars per month.

Obtaining a Boat

A live-abroad sailboat that can navigate the Caribbean will cost at least  $20,000 to $25,000 . If you want a more luxurious cruiser, be prepared to pay anywhere from $30,000 to $90,000. This is one of the most significant expenses you'll be required to make for your Caribbean journey.

You also have an option to charter a sailboat for much less money. However, it won't give you a lot in the way of customization.  

Maintenance of the Boat

So you've bought your boat – great! Now, you have to think about how much you're going to pay to maintain it. You'll pay anywhere from a  few hundred to a few thousand dollars  per year on servicing your sailboat, depending on its size. If you're navigating in the Caribbean, you'll need a mid-size sailboat, which will be at least 30 to 40 ft. long.

Most sailors prefer larger boats. If you've never sailed on open water before, you'll want to get the biggest and most robust boat possible. Managing such a boat will certainly cost you several thousand dollars per year. If you live aboard your boat all the time, you'll need to change the sails every few years because they'll wear out with excessive use. The cost of new sails is, again, thousands of dollars.

Paying Your Taxes

It would be best if you also thought about how you'll pay taxes while you're in the Caribbean. You don't need to pay income tax in your host country if you're just visiting there for a couple of months and still nominally residing in the U.S. This isn't unethical or illegal if you're only staying a few months in between. However, if you're looking to live in one particular country for a long time, make sure you get registered with that country's government.

You should have all this sorted out before you depart; however, you can also do it once you reach your destination – or even online. You could always contact the American consulate if you're not sure how to do it. They should be able to assist you.

Food and Other Supplies

Living on a boat is like living in a tiny home without the availability of a store in many respects. You'll need to stockpile enough food to last at least a month at a time. Because buying supplies in the Caribbean can be costly, many sailors want to take sufficient bottled and canned meals for their whole Caribbean journey when they depart the United States.

Estimate how much you're currently spending on these food types, eliminate many other fresh items, and calculate how much you'd spend on a menu that's mostly made up of meals that can be preserved for a long time because that is what you will need in the Caribbean.

If you really want to enjoy fine cuisine, a plunge into a refreshing pool now and then, and other pleasures, you will have to pay significantly more.

Marinas that appeal to the affluent and luxury yacht locations will charge a premium for all of their facilities. Decide on the type of lifestyle you intend to live in the Caribbean. To enjoy the luxuries, make sure you have the extra funds required to afford them; otherwise, they will affect your budget and might make it difficult for you to manage the necessities.

Water and Gas

When you visit a marina every few months throughout your Caribbean voyage, you'll need to fill up on groceries as well as water and gas.

These expenditures might add up quickly based on how often you use your engine and how much clean water you consume. Water can be pricey in some regions of the Caribbean, so it is important to keep that in mind.

Cost Breakdown

Some reasons to live on a sailboat in the caribbean.

Living on a sailboat in the Caribbean has several advantages. First, it gives you the freedom to cruise about and go wherever you choose. The Caribbean Islands are all staggeringly beautiful, and immigration laws aren't too stringent. When you arrive on a floating island, you will be switching countries; however, many will not require a passport upon arrival, making it quite efficient and easy.

Staying on your sailboat might also provide you with the solitude and serenity you're looking for. You can drop anchor wherever you want, preferably in calmer waters, and simply relax and unwind. Furthermore, staying on your boat provides you with the adventure that so many of us seek.

Exploring those historical islands while following the itineraries of long sunken commerce ships from pre-industrial Europe is a once-in-a-lifetime experience. Lastly, the Caribbean offers a wide range of experiences. The presence of so many nations and tourists from all over the globe has resulted in a genuine multicultural nation. This is the spot to go if you want to meet folks from all around the world from the comfort of your sailboat.

This also implies a plethora of restaurants to visit and beverages to try. The islands attempt to satisfy everyone.

Tips to Reduce the Cost of Living on a Boat in the Caribbean

Based on where you're from, staying on a sailboat in the Caribbean can be costing big bucks every month. However, there are a few cost-cutting options available as well.

Keep the Engine Off

If you don't sail around too much, you'll cut down on the amount of money you spend on gas and prolong the life of your engine. Relax and enjoy your Caribbean holiday by waiting for the wind to blow in the location you would like to go to. Also, make sure to  change the oil  on time as it would affect the amount of fuel consumed by your vessel.

Find Your Own Food

The Caribbean is home to some of the world's most abundant edible seafood. You can catch a wide variety of tasty fish and seafood. Look into fishing licenses and make sure you're obeying the rules in your area. Using your own catch as a source of food might help you save a lot of money.

After preparing a few healthy meals, you may discover that you aren't as concerned with having lavish dinners. You can also consider purchasing fresh fish directly from local fishers as it might save you a great deal of money compared to going to the store.

Make Full Use of the Marina – but Don't Stay for Too Long

Marinas are popular among sailors for a variety of reasons. Numerous people, cafes, and bars are available as well as housing. You can get off your boat onto dry ground whenever you choose to stay at a marina. You can also have a good time without having to worry about your boat dragging.

It's wonderful to treat yourself to a marina occasionally, but if you need to save cash on your Caribbean vacation, you should not stay at a marina for too long. Do some research to find the most affordable marinas at your preferred destination. Also, only stay there occasionally. This allows you to save some money on your trip.

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I'm Michael Moris. I've been sailing my whole life, and it has taken me to places I never imagined. From the Caribbean to Europe, from New Zealand to South America - there's nowhere that hasn't felt like home when you're on a boat!

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U.S. Couple Vanish from Yacht in the Caribbean: ‘It Looked Like a Robbery, or Something Much Worse’

Kathy Brandel and Ralph Hendry are presumed dead. The three fugitives believed to be connected to their case have been arrested but are not formally charged

sailboat in the caribbean

A catamaran captain was paddle-boarding along the St. Vincent shore when he came across a ransacked yacht with a broken, unrolled sail last month.

“It was not a very typical place to drop anchor,” Bernat Buj tells PEOPLE in an exclusive interview in the latest issue, on newsstands Friday. “And that caught my attention.”

Concerned, he boarded Simplicity , calling out three times in the hope of finding someone on board.

There was “a great mess throughout the ship, and I thought it was the scene of a robbery,” Buj says. “But when I entered a cabin and saw blood, I thought it could be something much worse .”

Bernat Buj, captain of Two Oceans catamaran

He found two American passports belonging to Kathy Brandel and Ralph Hendry .

Kathy – a retired real estate agent who would have turned 71 on Feb. 21 – and Ralph – a 66-year-old financial advisor who worked from their yacht – had been cruising in Grenada when they suddenly stopped communicating with family on Feb. 18, according to their sons, who stayed in touch with PEOPLE throughout the search for their parents .

Courtesy of Nick Buro

For more on the unfolding case of the missing American sailors in the Caribbean, subscribe now to PEOPLE , or pick up this week's issue, on newsstands Friday.

After finding the couple’s abandoned yacht – 80 miles from their last reported mooring – in Wallilabou Bay, St. Vincent, the captain reported the "unoccupied sailing vessel" to the local Coast Guard Service Feb. 21. 

“The entire interior of the vessel and its decks were ransacked,” the Coast Guard’s commanding officer wrote in an internal memorandum – obtained by PEOPLE – to the country's police commissioner.

Missing from the internal correspondence was the working theory between police forces in Grenada and St. Vincent that three Grenadian inmates who had escaped their holding cell the same day the couple went missing, had allegedly hijacked their yacht and thrown them overboard en route to St. Vincent.

The three fugitives – sailor Ron Mitchell, 30, Abita Stanislaus, 25, and Trevon Robertson, 19 – who had been arrested for a violent robbery in December, were re-apprehended on St. Vincent on Feb. 21. 

Royal Grenada Police Force

Video of one arrest, published by local media, includes shouts of “Gun! Gun! Gun!” and an escapee in his underwear, blood streaming down his legs as an official rounds him into the back of a pick-up truck. 

An insider close to the investigation alleges to PEOPLE that at least two of the men have confessed to Ralph’s and Kathy’s murders. 

The men, who were deported to Grenada on March 4, have not been officially charged in the case.  Although the couple’s bodies have not been found, they are presumed dead. 

Buj says he is still holding out hope. “I wish this story could have a happy ending,” he says.

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2025 Member Cruise to the Western Caribbean

Embark on the 2025 Disney Vacation Club Member Cruise to the Western Caribbean! This 5-night, round-trip Disney Cruise Line sailing departs from Fort Lauderdale, Florida on August 2, 2025, charting a course for family fun in dazzling tropical destinations—plus a first-ever Member Cruise visit to Cozumel.

Along the way, delight in commemorative keepsakes and experiences created with Members in mind—including onboard entertainment planned just for the Member Cruise!

Booking begins April 13, 2024.

Set Sail for Adventure

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A Disney Vacation Club Member Cruise elevates the already spectacular Disney Cruise Line experience.

Disney Cruise Line sailings offer fun and excitement for everyone in the family, from Broadway-style stage shows and delectable dining to unique onboard activities and spectacular fireworks at sea.

And a Member Cruise brings this already exceptional experience to a new level. Some of the best and brightest from the incredible Disney family of studios and storytellers will come together to present amazing “insider” shows. Additional standout features include commemorative keepsakes, themed décor and more—all crafted with our Members in mind!

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Embark on an exciting sailing to the Western Caribbean, with visits to 2 tropical islands brimming with activities for the entire family. Plus, enjoy 2 delightful days at sea—with access to signature Disney Cruise Line entertainment, imaginative themed dining, Broadway-style stage shows, refreshing pools, surprises for Members and more.

Explore the scheduled itinerary for the 2025 Member Cruise to the Western Caribbean:

  • Saturday, August 2, 2025 –Depart from Fort Lauderdale, Florida.
  • Sunday, August 3, 2025 –Enjoy a day at sea filled with unique experiences and special shows created with Members in mind.
  • Monday, August 4, 2025 –Arrive in Cozumel, Mexico, an island paradise renowned for its beautiful beaches, turquoise water and protected coral reefs.
  • Tuesday, August 5, 2025 –Enjoy another leisurely day at sea filled with unique experiences and special shows created with Members in mind.
  • Wednesday, August 6, 2025 –Arrive at Disney Castaway Cay, a private island paradise exclusive to Disney Cruise Line.
  • Thursday, August 7, 2025 –Debark in Fort Lauderdale, Florida.

Before or after your cruise, consider adding a little extra magic to your vacation with a stay at Walt Disney World Resort in Florida—located approximately 3 hours from Fort Lauderdale.

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Dreams really do come true on the award-winning Disney Dream, where classic beauty and modern luxury blend seamlessly with legendary Disney storytelling.

Onboard Fun

There’s an almost endless amount of one-of-a-kind entertainment, recreation and dining offerings to keep the entire family smiling from sun-up to well after sundown.

  • Dining –Feast on casual fare and gourmet delights at wondrously themed restaurants. Adults can also choose to indulge in romantic dining experiences at Palo or Remy.
  • Entertainment –Be front-and-center at original Broadway-style live shows, enthralled by brilliant fireworks displays, delighted by greetings from favorite Disney Characters and more.
  • Youth Clubs –Kids will love Disney’s Oceaneer Club—with its larger-than-life spaces fueled by Disney storytelling—while tweens can enjoy videogames, music and movies at Edge and teens can get together in the Vibe lounge for karaoke and dance parties.
  • Pools –Make a splash on the exhilarating AquaDuck water coaster, cool off in 2 family pools or relax at the Quite Cove Pool—an oasis exclusively for adults.
  • Fitness Center –Stay shipshape at a workout facility offering top-of-the-line weight machines and cardiovascular equipment, plus aerobics classes, yoga and more.
  • Goofy’s Sports Deck –Don’t miss this open-air activity center featuring a miniature golf course, a basketball court and virtual sports simulators.

Choose a stateroom that fits your family’s need for style and comfort—from cozy private lodgings with extra space to grand and richly appointed suites boasting sweeping views.

  • Concierge –Luxurious and spacious beyond compare, Concierge staterooms feature separate bedrooms, top-notch amenities and unparalleled service.
  • Verandah –Breathe in the ocean air from these richly appointed accommodations designed for families of 3 to 5—featuring a private balcony and sweeping sea views.
  • Oceanview –Relax in roomy quarters bedecked in a charming nautical motif with art deco flourishes—plus one or 2 portholes for admiring the scenery.
  • Inside –Sail away in a spacious stateroom fitted with a Magical Porthole for real-time sea views—and surprise sightings of animated Disney characters!

Learn more about Disney Cruise Line .

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Call Member Services at (800) 800-9800 or (407) 566-3800 † to book your spot.

Dedicated Support for Member Cruise Bookings

Member Services will be open from 10:00 AM to 6:00 PM Eastern Time on April 13, 2024 to book reservations for the 2025 Member Cruise exclusively —as well as to assist with any Resort arrivals occurring within 5 days of the April 13 date. Due to the popularity of the Member Cruise, you may experience longer-than-usual wait times.

Member Services will reopen with normal operations at 9:00 AM Eastern Time on Sunday, April 14 to support all Membership requests.

Simplify Your Booking Phone Call

We have adjusted this Member Cruise Booking Day process to improve our ability to quickly secure your stateroom and collect payment during your initial inbound call. To make your booking phone call go smoothly, please have the following information on hand about yourself and each person sailing with your party, including:

  • Member ID Number
  • First, second and third stateroom category choices, as popular options sell out quickly for this event
  • Special dietary needs
  • Special medical needs
  • Castaway Club Number (provided to repeat cruisers by Disney Cruise Line)

For each person sailing on the Member Cruise, please have the following information ready:

  • Legal name and middle initial, spelled as it appears in print on appropriate citizenship documentation
  • Physical home address (no P.O. boxes)
  • Home telephone number
  • Date of birth (mm/dd/yyyy)
  • Citizenship/nationality

To assist in your planning, you may wish to visit Disney Cruise Line  to view the ship layouts and general locations associated with the categories offered.

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Find out the booking information and general rules concerning this 2025 Disney Vacation Club Member Cruise. Please keep in mind that all reservations are subject to availability.

Please note:

  • Member Services will reach out to collect payment before May 13, 2023.
  • Booking requests will not be accepted by fax, email, live chat or Member Online Booking—or in person at the Disney Vacation Club Member Lounge at EPCOT or the Disney Vacation Club Star View Station – a Member Lounge at Disneyland Park. Call Member Services at (800) 800-9800 or (407) 566-3800 † to book your spot.
  • Additional fees may apply for recreational activities and Port Adventures.
  • Due to the unique nature of this special event, Disney Vacation Club has waived the policy of requiring at least one passenger to sail using Reservation Points for this Member Cruise voyage. If Members would like to pay by using both cash and Reservation Points, individual passengers must be paid for by using all cash or all Reservation Points.
  • Disney Vacation Club will waive the initial transaction fee associated with booking your Disney Cruise Line reservation for this Member Cruise voyage.
  • Disney Vacation Club will accept the following methods of payment for Members not using Reservation Points to book the cruise: Disney Gift Card, JCB, Visa, MasterCard, American Express or Discover. If paying by credit card, please have the credit card number, expiration date and the name that appears on the card available. Full payment is required at the time of booking.
  • For the safety of our Guests, women who have entered their 24th week of pregnancy as of the embarkation date or who will enter their 24th week of pregnancy during the cruise will be refused passage due to safety concerns. Neither a physician's medical statement nor a waiver of liability will be able to override the policy. Disney Cruise Line and Disney Vacation Club cannot be held responsible or liable for any complications relating to pregnancy at any stage.
  • Disney Cruise Line policy prohibits infants less than 6 months of age on the date of embarkation to travel.
  • Effective March 21, 2011, Members who do not purchase their ownership interests directly from Disney will not be able to use those Vacation Points to make reservations for the Member Cruise. If a Member wishes to pay entirely in cash, they must still own at least one Contract with ownership interests purchased directly from Disney Vacation Development, LLC. Effective June 3, 2021, to obtain a Disney Vacation Club Digital Membership Card, Members must accumulate a total of at least 150 Vacation Points purchased directly from Disney Vacation Development, LLC.
  • Members may book a maximum of 4 staterooms per Membership.

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Important Information About Membership Extras:

Membership Extras—such as exchange options in the Disney Collection and options offered through hotel exchange, certain discounts, offers and special events—are incidental benefits. These incidental benefits are subject to change or termination without notice, may require the payment of a fee and cannot be combined with any other offers or promotions. Membership Extras are also subject to availability and blockout dates may apply, including high periods of demand such as Christmas and New Year's Day. To receive any Membership Extras, purchasers must present a valid digital Disney Vacation Club Membership Card along with a corresponding valid photo ID.  Effective June 3, 2021, to obtain a Disney Vacation Club Membership Card, Members must accumulate a total of at least 150 Vacation Points purchased directly from Disney Vacation Development, Inc.  Exchange options in the Disney Collection and options offered through hotel exchange are not available for ownership interests not purchased directly from Disney Vacation Development, Inc. after March 21, 2011 and, effective April 4, 2016, Members who have not purchased an ownership interest directly from Disney Vacation Development, Inc. will not have access to Membership Extras.

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sailboat in the caribbean

sailboat in the caribbean

Royal Caribbean passengers can ignore this serious warning

While cruise ships serve as sanctuaries while they're at sea, on port days they face any problems affecting their destinations. 

Those issues could be benign — like some Caribbean nations having many of their stores and restaurants closed on Sundays — or more serious.

Royal Caribbean and Norwegian, for example, both have suspended cruises that leave from or call on ports in Israel. That makes sense because the region is currently at war. In addition, multiple cruise lines have stopped sailing to Russia because of its unlawful invasion of Ukraine. 

Related: Carnival Cruise Line makes a dining change, asks customers to tip

Customers know (or at least they should know) that every cruise line reserves the right to change an itinerary. Sometimes this happens before a cruise sets sail, and on other occasions it can happen during a sailing.   

In some cases the changes are weather-related: A storm might require a ship to take a longer route, which forces it to arrive in a port late or even miss a stop. When that happens — whether it's before a cruise or during — passengers will get their port fees and any money spent on excursions refunded.

Canceled ports are simply part of cruising, but Royal Caribbean  ( RCL )  has made clear that it won't stop sailing to one of its private destinations even though the U.S. government has issued a do-not-travel advisory for the country.

U.S. government issues a severe warning

Currently, the U.S. State Department has issued warnings about a number of very popular cruise destinations. All the major cruise lines, including Royal Caribbean, Carnival, MSC Cruises, Norwegian, Disney, and Virgin Voyages call on various ports in the Bahamas.

That's an area where the State Department has issued a Level 2 travel warning.

"Exercise increased caution in The Bahamas due to crime," the agency said on its website.

The cruise lines have not stopped sailing to the Bahamas, but they have passed on the warning to their passengers and, in some cases, have urged them to stick to the port area or cruise-line-sponsored excursions.

In the case of the Bahamas, the warning includes specific areas to avoid.

"The majority of crime occurs on New Providence (Nassau) and Grand Bahama (Freeport) islands," the State Department posted. "In Nassau, practice increased vigilance in the “Over the Hill” area (south of Shirley Street) where gang-on-gang violence has resulted in a high homicide rate primarily affecting the local population."

A second warning, however, urges travelers to simply not travel to Haiti, an island where Royal Caribbean has its own private destination.

Royal Caribbean still sailing to Labadee

The U.S. Embassy in Port Au Prince, Haiti, recently posted an updated warning from the U.S. State Department about Haiti. 

"The U.S. State Department’s Travel Advisory for Haiti remains at Level Four: Do not travel to Haiti. The current security situation in Haiti is unpredictable and dangerous. We are aware that there are few or no commercial options to depart Haiti safely at this time. As they become available, we urge U.S. citizens to take advantage of them," the embassy shared.

Despite this warning, Royal Caribbean, which has canceled sailings to its Labadee private destination in Haiti due to political unrest, has not done that now. 

“The safety of our guests and crew is our top priority," the cruise line said in a media statement. "Our global security teams are closely monitoring the situation in the area. At all times, we remind guests to remain aware of their surroundings while ashore and follow all State Department guidelines. Should any changes be required, guests will be notified directly." 

Labadee, while not an island like CocoCay, is actually part of mainland Haiti, about a seven-hour drive from Port Au Prince. It is technically part of Haiti, but it's a remote destination that's very far removed from the current fighting and political unrest.

Unlike a stop in Nassau or other Bahamas destinations, Labadee is a closed-off resort protected by military-like security. Passengers are not permitted to leave the secured area and the only excursions offered are within the area controlled and protected by Royal Caribbean.

Update: Royal Caribbean has sent a letter to passengers sailing on ships that dock in Labadee and has canceled some excursions.

"Out of respect to our local communities surrounding Labadee, Haiti, and to ensure our guest and crew safety, we're temporarily adjusting our tour offerings," read a letter sent to passengers and shared on Cruise Critic's community boards .

The cancellations effect jet ski and kayak trips as well as fishing excursions. Essentially, the cruise line wants to keep its passengers in its protected areas.

Refunds will be issued for all canceled excursions.

A Royal Caribbean ship leaves port. Royal Caribbean Ship Lead

Royal Caribbean cruises will no longer stop at a private beach in this Caribbean nation

  • Updated: Mar. 17, 2024, 1:05 p.m. |
  • Published: Mar. 15, 2024, 11:10 a.m.

Haiti

Royal Caribbean cruises will no longer stop at Labadee, a private beach in this Caribbean nation Canva

Royal Caribbean cruises will no longer set sail for Haiti, at least for the time being.

And it’s for safety reasons.

Royal Caribbean announced Thursday that its cruise liners won’t be stopping at its private beach in Labadee, Haiti, “out of an abundance of caution” as the country struggles with rampant gang violence and political turmoil.

“Due to the evolving situation in Haiti, and in an abundance of caution, we’re temporarily suspending our visits to Labadee for our entire fleet,” Assistant Vice President Aurora Yera-Rodriguez said in a statement . “We continue to monitor and assess the situation with our Global Security & Intelligence Team.”

The visit suspension will last for at least the next week, according to Michael Bayley, the company’s CEO.

“We have suspended calls into Labadee, Haiti, for the next 7 days and will continue suspension on a rolling basis with 3 days advance notification to our guests sailing on itineraries impacted and changed as we monitor and evaluate the situation in Haiti,” Bayley wrote in a Facebook post on Thursday.

Royal Caribbean describes Labadee as a private destination on Haiti’s northern coast with “pristine sands, coral reefs and jungle-covered hilltops nestling lagoon-like bays.”

“The safety and security of our guests, crew, and communities we visit are our top priority,” a Royal Caribbean spokesperson said Thursday in a statement to FOX Business . “Our Global Security and Intel Team is closely monitoring the evolving situation in Haiti, and in an abundance of caution, we are temporarily making adjustments to sailings visiting Labadee.

“We will continue to monitor and reassess calls as needed, and will communicate updates with guests directly,” the spokesperson added.

Royal Caribbean cited warnings from the U.S. government in its decision, which urged all American citizens in Haiti to leave the country last week. The U.S. Embassy in Port-au-Prince was also evacuated of nonessential personnel. A group of Marines were also deployed to protect the facility, The Hill reported.

The U.S. has urged people not to travel there as gangs have overrun the crime-riddled country since late last month after Prime Minister Ariel Henry left for Kenya to secure a United Nations-backed multinational security force and organized gangs broke out thousands of prisoners.

As a result, roaming gangs control about 80 percent of Port-au-Prince, according to the United Nations.

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3 escaped inmates from Grenada charged with murder after US sailing couple vanishes

Police transport escaped prisoners Atiba Stanislaus, far left, and Trevon Robertson who are handcuffed together in Kingstown, St. Vincent and the Grenadines, Monday, March 4, 2024. The men had escaped from a police holding cell in Grenada on Feb. 18 and are suspected of hijacking a catamaran while Ralph Hendry and Kathy Brandel, who disappeared, were aboard. (AP Photo/Kenton Chance)

Police transport escaped prisoners Atiba Stanislaus, far left, and Trevon Robertson who are handcuffed together in Kingstown, St. Vincent and the Grenadines, Monday, March 4, 2024. The men had escaped from a police holding cell in Grenada on Feb. 18 and are suspected of hijacking a catamaran while Ralph Hendry and Kathy Brandel, who disappeared, were aboard. (AP Photo/Kenton Chance)

The yacht “Simplicity”, that officials say was hijacked by three escaped prisoners with two people aboard, is docked at the St. Vincent and the Grenadines Coastguard Service Calliaqua Base, in Calliaqua, St. Vincent, Friday, Feb. 23, 2024. Authorities in the eastern Caribbean said they were trying to locate two people believed to be U.S. citizens who were aboard the yacht that was hijacked by the three escaped prisoners from Grenada. (AP Photo/Kenton X. Chance)

  • Copy Link copied

SAN JUAN, Puerto Rico (AP) — Three escaped inmates from the eastern Caribbean island of Grenada were charged in the killing of a U.S. couple whose catamaran they hijacked, police said Thursday.

Ron Mitchell, a 30-year-old sailor; Atiba Stanislaus, a 25-year-old farmer; and Trevon Robertson, a 23-year-old unemployed man, were charged with capital murder, escaping lawful custody, housebreaking, robbery and kidnapping. Stanislaus also was charged with one count of rape, according to a statement from the Royal Grenada Police Force.

The men appeared in court on Thursday and were ordered held in prison until their hearing in late March.

They were accused of escaping from a police holding cell on Feb. 18 and hijacking a catamaran owned by Ralph Henry and Kathy Brandel while they were aboard. Authorities said they believe the couple was thrown overboard as the suspects sailed to nearby St. Vincent, where they were arrested on Feb. 21.

The three men were ordered deported from St. Vincent on Monday.

The nonprofit Salty Dawg Sailing Association described Hendry and Brandel as “veteran cruisers” who participated in last year’s Caribbean Rally from Hampton, Virginia, to Antigua, and had planned to spend the winter cruising in the eastern Caribbean.

Their bodies have not been found.

sailboat in the caribbean

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    The Cayman Islands offer excellent boating infrastructure, clear waters, and a well-maintained coastline. St. Lucia boasts a picturesque coastline with beautiful anchorages and safe harbors. Antigua and Barbuda are known as the "Sailing Capital of the Caribbean.". These islands offer a wide range of anchorages, marinas, and services for ...

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    Sailboat Rental in the Caribbean. The Caribbean is an idyllic island destination with a vibrant and authentic culture. With a warm tropical climate through winter, steady sailing winds and a range of some 7,000+ outstanding islands to hop between, you can choose everything from uninhabited and remote outcrops to bustling port towns with a swinging nightlife for your sailboat rental in the ...

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    June 15, 2022. The best time to sail the Caribbean is during the beginning and end of summer when the weather is warm, and conditions are stable. The Caribbean is an extremely popular offshore sailing location, as conditions are usually manageable and accommodations are affordable. Most sailors spend time in the Caribbean during the summer ...

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  25. Royal Caribbean will evaluate canceling more visits to Labadee, Haiti

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  27. Royal Caribbean passengers can ignore this serious warning

    Update: Royal Caribbean has sent a letter to passengers sailing on ships that dock in Labadee and has canceled some excursions. "Out of respect to our local communities surrounding Labadee, Haiti ...

  28. Royal Caribbean cruises will no longer stop at a private ...

    Royal Caribbean cruises will no longer set sail for Haiti, at least for the time being. And it's for safety reasons. Royal Caribbean announced Thursday that its cruise liners won't be stopping ...

  29. Royal Caribbean International suspends sailings to Labadee, Haiti, for

    Royal Caribbean noted itinerary changes may vary by sailing. The cruise operator's stock was trading at $129.26 at noon, up 0.43% from the previous day's closing price. More Royal Caribbean ...

  30. 3 escaped inmates from Grenada charged with murder after US sailing

    Police say that three escaped inmates from the eastern Caribbean island of Grenada have been charged in the killing of a U.S. couple whose catamaran they hijacked. ... The yacht "Simplicity", that officials say was hijacked by three escaped prisoners with two people aboard, is docked at the St. Vincent and the Grenadines Coastguard Service ...