yachting in the caribbean

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Find Your Perfect Yacht

Caribbean yacht charters - one resource for every luxury charter yacht

The proven resource for crewed yacht charter in the caribbean.

From the moment you contact us, you will be helped by an experienced and knowledgeable specialist who will take the time to understand your unique needs and preferences for your caribbean vacation. They will be your dedicated specialist and our exceptional personal service will answer every question.

The largest choice of crewed Caribbean yachts?

Absolutely, with our relationships built over decades we truly do have access to EVERY crewed private charter yacht based in, or visiting, every part of the Caribbean.

Whatever the type of yacht for your Caribbean charter, your vacation budget, or the size of your party, our specialists will guide you in choosing the ideal yacht for your Caribbean charter. It's your vacation to explore the islands the very best way possible - on a Caribbean charter yacht.

Browse different types of Charter Yachts in the Caribbean

Motor Yachts

This category of Caribbean yachts include mega yachts, super yachts, and all sizes of power yachts. With the maximum space for guests, both inside and out, these types of yachts offer excellent vacations. You can choose from a fast, agile yacht, one that is high-end and luxurious, a yacht with a classic design, or one that is contemporary. This is one of the many choices you’ll have when you plan your vacation. See some yachts:-

Crewed Catamarans are very popular in the Caribbean , especially in the BVIs. Catamarans offer ample deck space that allows everyone to relax together during their charter, sharing the same views throughout the voyage. Caribbean catamarans can typically accommodate between 6 and 12 guests. See some yachts:-

Sailing Yachts

If you are looking for a winter getaway, there is no better place to charter a sailing yacht than the Caribbean! Feel the warm, tropical breeze on your face. Experience the exhilaration as the wind fills the sails and the yacht is suddenly moved along by just the wind. Savor the magnificent beauty of the Caribbean as you sail silently from one island to the next. Although typically offering smaller spaces for guests, sailboats deliver a truly unique caribbean charter vacations . See some yachts:-

Sample Charter Yachts in the Caribbean

ODYSSEA. The 59' sailing catamaran Odyssea is ready to take you and your guests on your next adventure. Throughout she offers relaxing areas to lounge and enjoy the voyage, while enjoying the company of others or absorbing the serenity of the sea. Her spacious cockpit area offers large dining table, sun pad across the back, and wet bar. See ODYSSEA :-

OKTO. Get ready for adventure when you step on board the 217' mega yacht Okto. You and your guests will find plenty to do, as she offers plentiful spaces for lying out to enjoy the sun, enjoying a movie in the circular cinema, working out in the indoor gym with an amazing view, or enjoying the on deck Jacuzzi. See OKTO :-

NAMASTE. The immaculately maintained mega yacht Namaste offers 121 feet of opulence at sea. She features five well-appointed cabins, both a main salon and sky lounge, sundeck with Jacuzzi, gym equipment, and a long list of watersports including jet skis, wakeboard, fishing gear, and the list goes on. See NAMASTE:-

NENNE. The 67' sailing catamaran Nenne was launched in 2017 by Fountaine Pajot, and was given a refit in 2020. With five cabins, she accommodates as many as ten guests, and has an impressive list of water toys that includes water skis for adults and children, wakeboard, standup paddleboards, fishing gear, snorkeling equipment, and the list goes on. See NENNE:-

MARIAH PRINCESS III. The 77' Lagoon built sailing cat Mariah Princess III was built in 2020. She offers two queen cabins and two king cabins, all en-suite. The master cabin has a private deck, the flybridge offers an on deck Jacuzzi, and she has a generous complement of watersports, including onboard SCUBA. See MARIAH PRINCESS III:-

TRUE STORY. The 67' sailing catamaran True Story is ready to give you and your guests a fun and exciting charter in the beautiful waters of the Caribbean. She offers a spacious main salon, large cockpit with al fresco dining and lounge, and flybridge with conversational area. You and your guests can also enjoy a long list of water toys throughout your journey. See TRUE STORY:-

The British Virgin Islands include Tortola, Jost Van Dyke, Virgin Gorda, and more. There’s no better way to experience the waters and beaches of the BVI's than on a private Caribbean charter with a full crew to pamper you. Of all the islands in the Caribbean, the Virgins are furthest north. This makes them very convenient due to the proximity to San Juan and due to their direct flights from the United States. Catamaran sailing vacations and crewed sailing charters are very popular in the islands, and their protected waters make them a favorite spot for guests that are taking their first private Caribbean yacht charter. To learn more about them:

The U.S. Virgin Islands consist mainly of the three large islands of St. Thomas, St. Croix, and St. John. With lovely bays, long beaches, lush nature preserves, fabulous diving spots, and excellent, onshore evening entertainment, many choose to vacation in the USVI’s. Caribbean charters often visit both the BVI’s and USVI’s during the same week, as they are close to one another and the waters are generally calmer than in other parts of the Caribbean. They in general are also home to the largest fleet of crewed, all-inclusive, luxury catamarans. To find out more about them:

The Leewards are situated in the middle of the Caribbean Island chain. The major airports are located on St. Maarten and Antigua. Due to the English, Dutch, and French influences everywhere you look, they exhibit the best example of cultural sophistication anywhere within the Caribbean. If you are looking to see where the rich and famous go on vacation, you will want to visit the island of St. Barts; for many this is a must stop for a Caribbean yacht charter. Many mega yachts are available for rental in St. Maarten, as it has become a popular mega yacht Caribbean base for the winter. To learn more about the Leewards:

The Grenadines are also called The Windward Islands. Oftentimes our guests will choose a sailing charter over a motor yacht when in the Grenadines, due to the more constant tropical breezes that occur. The islands are much less developed than the rest of the Caribbean, and the inhabitants live on their own time schedule, which enhances the feeling of getting away. The northern most island accessible by air is ST. Vincent, while the southern tip’s major airport is on Grenada. There are fewer Caribbean charter yachts based here; however, occasionally some charter yachts are happy to relocate in order to offer a vacation that happens a little off the beaten path. To find out more about the Grenadines:

What Type of Charter Yacht?

There are all types of Caribbean yacht charters available, including mega yachts, power yachts, catamarans, and sailboats. We have helped countless clients choose the right charter yacht, learning what features and amenities make a difference on caribbean charter yachts. Learn more about different types of Caribbean yachts.

Where Can You Go?

Typically you’ll choose between the Virgins, Leewards, and the Grenadines to charter your yacht. Beyond the region, it is your Caribbean to explore. It’s important for you to remember that there is no cruise ship itinerary to worry about! Your itinerary will be custom designed specifically for you, with you, and is flexible to changes during your charter. We have put together some samples for you to get an idea of what you might like to do while on vacation in the Caribbean. Interested in seeing a sample cruise itinerary ?

Find Your Perfect Yacht for a Caribbean yacht charter

To see the Caribbean yachts we have in our online database, please select a yacht type and your budget below. Please keep in mind that we do not have every available yacht online. There are many more yachts available for you to choose from when you contact one of our specialists.

For your personalized selection including yachts not online:- Email us now

Caribbean Charters - When To Go.

One of the lovely things about the Caribbean is that the temperatures remain consistent throughout the year; however, there are some other weather considerations that you will want to factor in when making your caribbean yachting vacation plans. Read More....

Vacations here are most popular between November and July.

If you are thinking of a megayacht, you will want to keep in mind that many of these private yachts which are Caribbean based in winter leave in the late spring and early summer months. They will return again in early winter; however, this does limit their availability. To charter a mega yacht, you will want to make sure that you do so well in advance.

Motor, sail, or catamaran yachts, on the other hand, often have selections available year round. Holidays like Christmas, New Year’s, and Easter do need to be planned for as early as possible as these are very popular charter times.

The availability for Caribbean charters can also be affected by the weather in other climates, for instance, when the severity of the weather is bad in the United States or Europe, especially between January and February, the charters are often booked. This is due to many clients looking for a break from the cold.

What Do Our Clients Say About The Caribbean?

Are you excited yet? You should be! Our clients have enjoyed fantastic Caribbean vacations. There is an endless number of places to visit in the Caribbean, from smaller islands to absolutely must be seen locations like St. Barts. Read some of our Caribbean charter reviews from clients who booked a Caribbean charter with us.

Ready to learn more about Caribbean charters?

We are specialists who will make your trip a reflection of our expertise! We know clients need to be confident in their charter vacation plans, so we encourage our clients to benefit from the knowledge base we’ve been building for years. You’ll speak to an authority on Caribbean charters without any obligation on your end.

Test our expertise with your questions!

Contact a specialist - available 7 days a week.

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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

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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.

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Area Guide: Caribbean Charter Destinations

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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Best Sailing Destinations In The Caribbean

Last Updated by

Daniel Wade

August 30, 2022

The Caribbean is one of the most beautiful and favorable seas to sail, and there are numerous breathtaking islands to visit.

The best sailing destinations in the Caribbean Sea are Puerto Rico, Belize, the Cayman Islands, the U.S. Virgin Islands, Saint Lucia, the British Virgin Islands, Guadeloupe, the Grenadine Islands, Grenada St. Vincent, and Antigua.

In this article, we'll cover ten of the top sailing destinations in the Caribbean region. We'll touch on the destination's history, scenery, and sailing accommodations, along with other attractions unique to the islands.

We sourced the information in this article from travel guides and the testimony of sailors who frequent the Caribbean islands and the Gulf of Mexico.

Table of contents

‍ Sailing in the Caribbean

The Caribbean is a highly popular sailing destination, especially for sailors in the southern and eastern United States. The region is tourist and boat-friendly, and it offers some of the most picturesque islands and coral reefs in the world.

Caribbean sailing promises warm weather and gorgeous water, which is warm enough to swim in year-round. Hurricane season can be a challenge, but the threat is reduced thanks to modern weather technology and careful planning by the sailor.

Here are ten of the best and most beautiful sailing destinations in the Caribbean, along with some of the best attractions to visit.

Top 10 Caribbean Sailing Destinations

We researched the most popular and unique sailing destinations in the Caribbean and found ten countries and island chains that stand out. These locations are accessible to American sailors, and some are U.S. territories that don't require citizens to go through customs.

1. Puerto Rico

Puerto Rico is a U.S. commonwealth located in the northeast of the Caribbean. The island is inhabited by just over three million people, and it's one of the most populous sailing destinations in the region. Puerto Rico is a beautiful island with warm weather and luscious scenery, making it a great destination to sail.

As a populous territory, Puerto Rico has all of the modern infrastructure you'll need. It has full-service marinas, boat repair facilities, and plenty of local spots for food and drink. It's an excellent place to stop for supplies or to spend a week or two. It's one of the most pleasant tropical vacations you can have.

Additionally, Puerto Rico uses the U.S. dollar as its primary currency, so you won't have to deal with currency exchanges and other hassles. U.S. citizens don't need a passport to visit the island, and U.S. flagged sailboats have an easy time finding accommodations. You don't even have to go through customs. However, you will need to bring a U.S.-issued ID card.

Belize is a country in Central America located on the western edge of the Caribbean. The country is known for its tropical forests and sparse population, making it an excellent destination for sailing adventures. Belize is also home to numerous ancient Mayan ruins, which are a major attraction with huge cultural and historical significance.

Belize also has numerous marinas and anchorages, as the country often caters to private boats along its coastline. The coast of Belize offers spectacular views of the ocean floor and marine life, with dozens of natural coves and inlets that serve as ideal anchor-outs.

The natural environment of Belize is stunning, but it's not the only attraction in this tropical region. Belize is home to several well-known resorts and coastal destinations, which offer luxury accommodations, food, drink, and lodging.

3. The Cayman Islands

The Cayman Islands were probably discovered by Christopher Columbus in 1503. The once uninhabited chain of islands, located south of Cuba, offers spectacular sailing and sightseeing. The islands include Little Cayman, Cayman Brac, and Grand Cayman (the largest). Today, the Cayman Islands are a British Commonwealth with about 71,000 inhabitants.

The Cayman Islands are home to spectacular anchorages and an occasionally rocky waterfront, with excellent beaches and marine life. The weather is tropical and warm, and the islands aren't far from the continental United States. Everyone here speaks English, so it's easy to find good accommodations and to socialize.

The Cayman Islands are home to several marinas, charter services, and even a sailing club. The shallow and clear waters surrounding the island make for excellent scuba and snorkeling, and the weather is almost always warm and favorable. Just watch out for hurricanes, which sometimes cross over the island during peak summer months.

4. The U.S. Virgin Islands

The U.S. Virgin Islands is a United States territory officially home to around 100,000 people. Like Puerto Rico, the U.S. Virgin Islands are an easy sailing destination for U.S. citizens. The small chain of tropical Caribbean islands uses the U.S. dollar as its primary currency, and English is the official language.

The islands have a total area of about 133 square miles, making them one of the smaller destinations on our list. The islands are located immediately adjacent to the British Virgin Islands, which are another top sailing destination.

Shallow waters along the coastline make the U.S. Virgin Islands an excellent place to dive, as the region is rife with marine life. There are dozens of smaller islands around the primary islands, which offer opportunities to explore secluded natural destinations.

5. Saint Lucia

Saint Lucia is a Caribbean nation that's known for its beautiful sailing conditions and majestic mountainous islands. The island is also home to luxury resorts and good services, along with protected anchorages for sailboats and yachts.

The official language on the island is French, but most sailing destinations have staff that speak English. The beaches on the islands are some of the best in the world, and the landscape is teeming with tropical plants, brightly colored flowers, and wildlife.

Like most Caribbean sailing destinations, the water around the island has shallow spots that are great for scuba diving and snorkeling. Saint Lucia is an excellent destination for photography due to its unique and iconic rock formations.

6. The British Virgin Islands

The British Virgin Islands are located right next to the U.S. Virgin Islands, and they offer some of the same excellent sailing that the U.S. Virgin Islands offer. This chain of islands is home to about 30,000 people. Sailing is a huge part of life here, and it's the only way to reach many of the most desirable locations.

These small islands are still a commonwealth of the United Kingdom. That means that English is the official language at all British and U.S. Virgin Islands sailing destinations. The official currency is the U.S. dollar, which makes transactions hassle-free for Americans. The islands host an annual regatta which is a great way to make friends from around the world.

The British Virgin Islands have excellent tropical scenery but also numerous coral reefs and rock formations to explore. For example, the Baths of Virgin Gorda are a mystical and popular natural wonder to explore on the islands.

7. Guadeloupe

Located in the Les Saintes archipelago, Guadeloupe is an excellent sailing destination with services and gorgeous spots to anchor out. The island is particularly popular with experienced sailors, and it offers plenty of opportunities to socialize without the crowding of islands that attract more tourists.

Guadeloupe is a French territory with luscious forests and a beautiful coastline to explore. The main island is almost entirely forested, which provides a rare and mostly untouched view of natural tropical life. The largest city, Basse-Terre, is home to the majority of the islands' 395,000 people.

French is the official language on the islands, though many people speak English, and there are facilities for immigration and customs work to be completed. Additionally, since the Island is controlled by France, it's part of the European Union and accepts the euro.

Note that on older charts, the regions of Saint Barthelemy and Saint Martin may be included as part of Guadeloupe, but these regions had a referendum and were detached in 2003. Nonetheless, these nearby destinations make for excellent sailing and exploration.

8. Grenadine Islands

The Grenadines are a world-class sailing destination, with several small islands making up the larger chain. These islands are known for their tropical beauty and seclusion, making them the perfect destination for quiet family trips to the tropics.

Many islands in the Grenadines were once privately-owned but are now uninhabited and rife with stunning scenery.

The rocky Grenadine Islands have numerous reefs and lots of places to anchor out, meaning that the islands can be a fun and affordable place to stay. The island of Carriacou is home to the majority of the population and offers some services to sailboats and other vessels.

9. Grenada St. Vincent

Grenada, a region home to numerous islands, including the Grenadines, is also home to St Vincent. This volcanic island is green and well known for its natural beauty. The capital city Kingstown is home to numerous hang-outs such as bars and restaurants, and it's just one of several seaside towns to explore.

One of the most popular tourist destinations on the island is the Botanic Gardens St. Vincent. The area, which is undergoing constant conservation work, is home to numerous tropical plants and animals, along with colorful and rare island birds.

10. Antigua

Antigua is a flower-shaped island that's known for its rare wildlife and beaches. The island, which has remained mostly isolated for centuries, is home to some of the world's rarest animals, such as the Antiguan Racer snake and the Griswold's Ameiva lizard.

Antigua is an excellent example of the weather and scenery that the Caribbean has to offer. It's a popular destination for sailing and yachting, and there are facilities around the island that cater to sailboats and help owners complete all the travel paperwork.

Antigua is home to a massive regatta that draws hundreds of fast sailboats annually. Antigua Sailing Week is a world-renowned event that's a blast to participate in and watch. During the rest of the year, the island hosts hundreds of boats throughout its many protected coves and inlets.

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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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Exploring the High Seas: A Guide to the Best Yacht Charter Destinations in the Caribbean

Embark on an enchanting voyage through the azure waters of the Caribbean, where hidden treasures await. Delve into the world of luxury yacht charters as we unveil the top destinations that redefine opulence and adventure. Explore the idyllic British Virgin Islands, where paradise meets the sea. Uncover the secluded gem of St. Lucia, a haven for those seeking solace amidst nature’s beauty. Sail through history in Antigua and Barbuda, and discover the untouched coves and pristine beaches of the Grenadines. Welcome to a world of innovation and exploration on the high seas.

British Virgin Islands: Paradise in the Caribbean

The British Virgin Islands offer an idyllic paradise for yacht charter enthusiasts in the Caribbean. With their pristine beaches, crystal-clear turquoise waters, and a multitude of islands to explore, this destination is perfect for those seeking beachfront luxury and unforgettable experiences.

One of the highlights of a yacht charter in the British Virgin Islands is the opportunity for island hopping. With over 60 islands and cays to choose from, each with its own unique charm, there is always something new to discover. From the lively atmosphere of Tortola to the tranquil beauty of Virgin Gorda, every island has its own distinct character and attractions.

For those who love underwater exploration, the British Virgin Islands offer exceptional snorkeling adventures. The coral reefs teem with colorful marine life, providing a breathtaking underwater experience. Whether you’re a beginner or an experienced snorkeler, there are plenty of spots to choose from, each offering a unique glimpse into the vibrant underwater world.

Sailing excursions are also a popular activity in the British Virgin Islands. With constant trade winds and calm waters, it is the perfect destination for sailing enthusiasts. Experience the thrill of gliding across the waves as you explore the hidden coves and secluded beaches that can only be reached by boat.

Please call or email Doug (our seasoned yacht travel specialist) today at (781) 679-1162 or email at [email protected] .

St. Lucia: A Secluded Yacht Charter Gem

St. Lucia offers a secluded haven for yacht charter enthusiasts in the Caribbean. With its stunning landscapes and untouched beauty, this hidden gem provides a unique experience for those seeking tranquility and luxury. Here are four reasons why St. Lucia should be on your yacht charter itinerary :

• Secluded anchorages : St. Lucia boasts numerous secluded anchorages, allowing you to escape the crowds and enjoy the serenity of the Caribbean Sea. From hidden coves to secluded bays, you can experience ultimate privacy and relaxation.
• Luxury resorts : St. Lucia is home to some of the most luxurious resorts in the Caribbean. After a day on the water, indulge in world-class amenities and pamper yourself at the exclusive resorts dotted along the island. Immerse yourself in opulence and unwind in style.
• Volcano hikes : St. Lucia is renowned for its dramatic landscapes, including the iconic Pitons. Embark on a volcano hike and witness the awe-inspiring beauty of the Soufrière volcano. Traverse lush rainforests, explore sulfur springs, and take in breathtaking panoramic views from the top.
• Local cuisine and marine life encounters : St. Lucia offers a blend of rich flavors and vibrant culinary traditions. Sample local delicacies, such as fresh seafood and tropical fruits, and savor the unique tastes of the island. Moreover, dive into the crystal-clear waters and encounter an array of marine life, including colorful coral reefs, tropical fish, and even sea turtles.

St. Lucia truly is a secluded yacht charter gem, offering a perfect blend of natural wonders, luxury, and adventure.

Antigua and Barbuda: Sailing Through History

Antigua and Barbuda offers a captivating journey through history for yacht charter enthusiasts. With its rich maritime heritage and historical landmarks, this Caribbean destination is perfect for those seeking a unique and educational experience. One of the must-visit sites is Nelson’s Dockyard, a UNESCO World Heritage Site that showcases the colonial architecture and naval history of the region. Built in the 18th century, this historic dockyard was once the headquarters of the British Royal Navy in the Caribbean and played a vital role in protecting the British interests in the region.

As you sail through the crystal-clear waters surrounding Antigua and Barbuda, you’ll be transported back in time, imagining the bustling activity of the naval base during its heyday. The colonial architecture of the dockyard, including the Georgian-style buildings and the historic forts, adds to the charm and authenticity of the experience.

In addition to the historical landmarks, Antigua and Barbuda also hosts various cultural festivals that celebrate the islands’ vibrant history and traditions. From the Antigua Sailing Week to the Antigua Carnival, these events showcase the local culture through music, dance, and traditional cuisines.

Embarking on a yacht charter in Antigua and Barbuda is not just about enjoying the natural beauty of the Caribbean, but also about immersing yourself in the fascinating history and heritage of the region. So, set sail and embark on a journey through time in this enchanting destination.

Grenadines: Discovering Hidden Coves and Pristine Beaches

When exploring the high seas in the Caribbean, yacht charter enthusiasts can uncover hidden coves and pristine beaches in the Grenadines. This stunning archipelago, located between St. Vincent and Grenada, offers a tranquil escape from the bustling tourist destinations. Here, visitors can immerse themselves in the beauty of nature while enjoying a range of activities and experiences.

• Exploring Marine Life : The Grenadines boast a rich marine biodiversity, making it a paradise for snorkeling enthusiasts. Dive into the crystal-clear waters to discover vibrant coral reefs, tropical fish, and even the occasional sea turtle or stingray.
• Snorkeling Adventures : Charter a yacht and visit the Tobago Cays Marine Park, a protected area with five uninhabited islands. Snorkelers can swim among colorful coral gardens and encounter an array of marine creatures, including friendly nurse sharks.
• Local Cuisine : Indulge in the flavors of the Grenadines by sampling the local cuisine. From fresh seafood dishes to traditional Caribbean delicacies, every meal is a culinary adventure. Don’t miss out on trying the national dish, Callaloo Soup, made from leafy greens and spices.
• Cultural Immersion : Get to know the locals and immerse yourself in the vibrant culture of the Grenadines. Visit the charming island of Bequia, known for its traditional boat-building heritage and lively regatta festivals. Engage in local traditions, such as dancing to calypso music and exploring the colorful markets.

For those seeking a luxurious experience, there are various luxury yacht options available for charter in the Grenadines. With their state-of-the-art amenities and expert crew, these yachts provide the perfect setting for a memorable Caribbean adventure.

Bahamas: Yacht Charter Haven in the Caribbean

The Bahamas, a yacht charter haven in the Caribbean, offers a captivating blend of pristine beaches, crystal-clear waters, and luxurious amenities for those seeking an unforgettable high seas adventure. With its stunning natural beauty and world-class facilities, the Bahamas is a dream destination for luxury yachting enthusiasts.

Bahamas yacht charters provide the perfect opportunity to explore the exquisite beaches that dot the archipelago. From the famous pink sands of Harbour Island to the secluded coves of the Exumas , the Bahamas offers a variety of beach experiences for every taste. Imagine stepping off your yacht onto powdery white sands, surrounded by turquoise waters and lush tropical landscapes. It’s a paradise unlike any other.

For those who love to explore the underwater world, the Bahamas is a snorkeling haven. The clear waters are teeming with vibrant coral reefs and a diverse array of marine life. Snorkelers can immerse themselves in an underwater wonderland, swimming alongside tropical fish, turtles, and even dolphins.

Fishing enthusiasts will also find their bliss in the Bahamas. The waters are rich with game fish such as marlin, tuna, and mahi-mahi. Whether you’re a seasoned angler or a beginner, the Bahamas offers ample opportunities for a thrilling fishing adventure.

In conclusion, the Caribbean offers a plethora of yacht charter destinations that cater to every traveler’s preferences . From the stunning beauty of the British Virgin Islands to the secluded charm of St. Lucia, and the rich history of Antigua and Barbuda, there is something for everyone. The Grenadines provide hidden coves and pristine beaches to explore, while the Bahamas offer a haven for yacht charters. Embark on a memorable journey and experience the wonders of the Caribbean’s high seas.

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Use our quick contact form to give us the basics about what you’re looking for and we’ll send you ideas and pricing. Don’t worry if it’s not grand enough or should be scaled back; we’ll take care of that too. When you love the plan, we put it into action. All you have to do is show up and enjoy.

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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. .

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.

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.

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

British Virgin Islands

US Virgin Islands

Puerto Rico & Spanish Virgin islands

Cayman Islands

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

Antigua & Barbuda

Martinique, St Lucia & The Grenadines

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

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Caribbean Yacht Charter: Everything You Should Know

If you’re thinking about someplace warm for some sun and sailing, the Caribbean may be the first places you might think of. But what’s involved in chartering a boat in the Caribbean? Where can you go, and how is the sailing?

Since there’s a lot to know about chartering a boat, we’ve put together your comprehensive guide to putting together your perfect getaway.

Where are the Caribbean Islands?

Why are the Caribbean islands so popular for yacht charters?

The Caribbean lures vacation travelers for so many reasons, but it’s very compelling for sailors. The region is steeped in romantic nautical history, and each island is a distinct cultural experience. And the weather, of course!

The Caribbean islands have warm and sunny weather all year round

Even in hurricane season, the weather is pretty nice. But when Europe and North America are buried in snow and ice during the deeps of winter, a white sand beach in the Caribbean becomes the clearest vision of paradise. At the worse, have a light sweater or sweatshirt on board for some cool but pleasant evenings. But it’s never cold , and days are always warm.

The Caribbean is a vast playground on a yacht

Most Caribbean sailing is easy and fun. Small islands lie within easy sail of each other, and most island nations are a day sail apart. The water is deep, the trade winds are consistent, and the sailing conditions are almost always perfect. Clear water and bright sun make navigation easy, and much of it is by line of sight.

You can have fun island hopping in archipelagos like the British Virgin Islands or St. Vincent and the Grenadines without changing countries. But sailing to another country, clearing in and out and getting a new stamp on your passport? That’s fun, too, and gives you an overnight change of scenery. Not just the landscape, but the entire culture and vibe can change with a few hours of sailing.

There are many beautiful resorts in the Caribbean where tourists come to stay for a week. But on a charter yacht? You get to see a lot of different resorts and gorgeous spots at your own pace.

Most Caribbean islands aren’t overrun by tourists

The mass tourism in the Caribbean is primarily from cruise ships, and in a charter yacht it’s easy to avoid them because you can get to places the cruise ships can not. Even with cruise ships plying the islands, there are very few highly built up and developed areas. And many places that are green, quiet, and inviting.

Certainly, there are resorts, hotels, and even some cities. But the islands also are places where people live , and there are wild places on all of them. Some islands have taken it further and leaned into ecotourism and preserving natural beauty. They build resorts to blend into the jungle and wilds or on the beaches, and the tours and activities get you out in nature.

Even at its most crowded, you’ll never have that packed theme-park experience. There’s always natural beauty and a calmer, more authentic pace of life.

Each island of the Caribbean has a distinct culture and unique history

People have lived in the Caribbean for thousands of years. Indigenous peoples like the Carib, Arawak, Taíno, and others settled the islands of the Caribbean long before the first Europeans arrived. Many of these populations didn’t survive the Europeans, but their cultural legacy still exists.

European colonization reshaped the Caribbean by establishing settlements, plantations, and military bases to further their government’s economic interests. Slaves imported in large numbers, along with European settlers and planters, swelled the population. The French, English, Spanish, Dutch, and Danish all established colonies (or tried to) and claimed various pieces of the islands. And every one of them left their mark.

The modern Caribbean has a mix of languages and cultures, with independent countries and territories from the U.K., France, and the Netherlands. A few islands are split, like Saint Martin/Sint Maarten, with its distinctive French and Dutch sides. People have mixed these histories to create their own cultural fusion, resulting in languages that combine native words, European languages, and other influences.

No matter which island you start on, every time you change ports, you’ll find something a little different.

There is a party-vibe in the Caribbean that you can’t find anywhere else

Getting to the Caribbean

Most of the Caribbean is easy to get to from Europe and the United States. Most flights from the U.S. connect through somewhere in Florida, to shorten the last flight. Direct flights are available from all the major European capitols, though you may need to connect on regional airlines for some islands.

Visas and paperwork

If you’re flying in to one country for your charter and not leaving it, you’ll do all your clearing in at the airport. Visa waiver treaties allow you to visit most Caribbean countries without a complicated visa proc’re from a participating country. Everyone in your party will need a passport, of course, but any visas or stamps will happen when you arrive.

If you plan to sail between countries on your charter, visas shouldn’t pose a challenge, either. Check with your charter company for specifics, as they may have restrictions and rules about sailing ranges. And they also have paperwork you’ll need to clear the boat in when you arrive.

Flying to the islands

Flights from the United States are shorter and more numerous, but there are plenty of flights from Europe even if they’re longer because of the distance.

No matter where you’re coming from, start looking at flights before you book your charter. Look closely when booking a major carrier headed to a smaller island. There’s a chance your last hop will be on a smaller inter-island plane. So make sure you meet all the baggage requirements and limits if you have to island hop.

Flying between the islands

Regional airlines connect all the islands, so check schedules for brief visits or extended stays. Most of the planes are smaller commuter planes, and may have limitations on baggage weights, so plan well.

Currency Conversions and Payments

Because there are multiple countries and legal jurisdictions in the Caribbean, there are also many currencies. While larger businesses take credit and debit cards, your bank may charge international transaction fees, even if the island nation uses the same currency.

Much of the Caribbean has standardized on the East Caribbean Dollar (XCD) which has a fixed conversion rate to U.S. dollars at $1.00 USD = $2.70 XCD. Other countries may use U.S. Dollars, Euros, or other currency.

Sometimes you can pay for things with different currencies on the spot, but don’t expect a good exchange rate. No one must accept foreign currency, and many don’t want the hassle unless you’re paying a lot more than you need to. So it’s a good idea to get a few local bills in your pocket when you arrive. It will ease your way and save you overpaying with big foreign bills.

What are the most popular destinations for yacht charters in the Caribbean?

The Caribbean has over 700 islands, reefs and cays grouped into thirty different political territories. Some are very easy and popular for chartering, and many are less accessible. Islands without charter bases are still interesting to visit. But some islands like Cuba can be logistically and politically difficult to visit for a vacation, especially on a U.S. passport.

The Dominican Republic and Haiti have difficulties because of their exposed coastlines and distance from other islands. It’s not that you can’t charter in these places, but there’s a reason other places are more popular.

The most popular destinations have visa waivers with the US, EU/Schengen areas, UK, and other countries. So pre-approved visas are not needed if your passport is from those nations.

You’ll find multiple languages spoken on most islands, including creoles and local dialects. So even if you don’t speak the language, there’s a good chance you’ll find someone who speaks a language you do.

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The Best Yachting Destinations In The Caribbean & How To Get There

Why the caribbean.

With the perfect mix of culture, pristine beaches and ideal sailing conditions, the Caribbean is a top yachting destination with racers, families and cruisers alike. Drawn by the steady NE trade winds, creole cuisine and infamous rum; visitors enjoy a tantalising tropical climate continuously hovering between 24C-32C.

As if that isn’t enough to tempt you, exhilarating racing regattas and diverse land and seascapes, mean that the Caribbean has something to offer everyone. Hosting over 25 island nations, each with their own unique draw, you would not be alone in struggling to decide where to take your next adventure!

Over the years, sponsoring events such as Antigua Sailing Week and the ARC; our Caribbean destination experts have gathered top recommendations from sailors just like you.

When is the best time to sail the Caribbean?

The Caribbean predominantly has 2 distinct seasons – a wet, and a dry season:

• Rainy season coincides with summer in the Northern Hemisphere – May to Oct
• Dry weather can be expected during the winter months – December to April

Though Hurricanes are known to sweep through the region from time to time, they occur between June and November meaning Peters & May’s regular Transatlantic Eastbound Sailings can get you back on home ground before Hurricane season begins.

Antigua has been a top yachting destination for centuries with Falmouth Harbour often labelled as a ‘Mega Yacht Haven’. Bursting with colonial history, Antigua’s colonial roots make the island a historic treat for visitors. For those looking for a more active visit to the region Antigua is at the hub of Caribbean racing regattas throughout the year.

Currency:  Eastern Caribbean Dollars

Language:  English

MUST visits:

• Nelsons Dockyard and The English Harbour
• Stingray City – visit by boat this shallow pool, full off sting ray
• Frigate Bird Sanctuary – Barbuda

As the home of  Antigua Sailing Week  and the finishing point for the Christmas Caribbean Rally and independent crossings, Antigua is a yachters paradise. During April – May over 1500 participants take to the waters around Antigua, ready for the rally. Here at Peters & May we love Antigua Sailing Week attending it every year. As the main sponsor of the event, Peters & May in collaboration with Antigua Sailing Week host the  Peters & May Round Antigua Race  which kicks off the event every year. Titled the official logistics partner to the event, Peters & May provide bespoke mast up sailing solutions to many a participant every year. Another event not to be missed is the RORC Caribbean 600 which starts in Antigua before heading around 11 islands to the finish line.

Closest P&M port:  Antigua

St Vincent & The Grenadines

Lush rainforests, idyllic beaches and tropical lagoons epitomise these islands laying in the Southern proportion of the windward islands. With 32 to choose from, you can while away hours with plenty to get involved in.  Natural anchorages, protected waters and specialist marine services across St Vincent and the Grenadines make it yachting paradise.

Currency:  Eastern Caribbean Dollars

• The crystal-clear waters of Tobago Cays
• St Vincent Montreal Gardens & Vermont Nature Trail

One of the regions most renowned events is that of the Bequia (Easter Regatta) which occurs in April every year – full of sailing and street parades,  Bequia Regatta   is one of the most well attended in the Southern Caribbean region.

Closest P&M Port:  Martinique

Lying in the South of the Caribbean, St Lucia has a lot to offer visitors. Its volcanic interiors create some of the most dramatic scenery in the Caribbean, perfect for a unique yachting get away like no other. With a range of onshore and offshore activities to keep you occupied, you will be left wanting more!

• Diamond Falls Botanical Gardens
• Sulphur Springs Park – enjoy steaming pools on this dormant volcano.
• Rainforest Trekking – 19,000 acres of rainforest to explore!

The home of the  ARC  in the Caribbean, every year in December for the last 20 years ARC participants have been welcomed on shore at St Lucia’s Rodney Bay after their Transatlantic crossing from Las Palmas, Grand Canaria. Full of community spirit and exciting sailing, it’s an event not to be missed. As an  official logistics partner  to the World Cruising Club, you will always catch some Peters & May representatives there and ready to talk about shipping you home!

Closest P&M Port:  Martinique

Saint Barthélemy

Known for its slick glamour, St Barths is the place to be for superyachts and yachts seeking a touch of luxury. Sapphire blue waters line great beaches proving quite the attraction to thousands of visitors each year.

Currency:  EUR

Language:  French

• Snorkelling and diving in the nature reserve of Saint Barthélemy.
• St Barths Film Festival at the end of April
• Saline Beach – one of the best beaches in the Caribbean.

St Barths is renowned for  St Barths Bucket Regatta , which attracts some of the largest Superyachts in the world. This event is invitation only for yachts over 30.5m, held during March off the waters of Saint Barthélemy. Come April, the  Les Voiles de Saint Barth  kicks off, a high-profile regatta open to all with maxi yacht, multihull and CSA classes.

Closest P&M Port:  Antigua & Tortola

British Virgin Islands

Labelled as the sailing capital of the world, consistent winds and small distances between islands make the British Virgin Islands perfect for island hopping. Some of the Caribbean’s best bars, marinas and spas can be found here as well as numerous natural wonders.

Currency:  USD

Language:  English

• The Virgin Gorda Baths are the BVI’s most famous landmark, sea pools and grottoes make it a busy anchorage point perfect for snorkelling.
• Hike up Gorda Peak National Park
• Smuggler’s Cove in Tortola – an undeveloped patch perfect to escape to.

Every year the islands host the  British Virgin Islands Spring Regatta  and Sailing Festival at the Royal BWI Yacht Club. With over 60 boats participating it is known to be an unforgettable sailing extravaganza, with a brilliant mix of international crews and a range of boats. This Caribbean Regatta has something for everyone, whether that be racers, cruisers, or those just looking for a good time.

Closest P&M Port:  Tortola & St Thomas

Comprising of 700 islands, ranging from uninhabited paradises to bustling resorts the Bahamas is a strong contender on the top yachting spots within the region. Although not technically Caribbean, it’s too good to miss off our top yachting list!

Currency:  USD & Bahamian dollar

• Dean’s Blue Hole in Long Island – The second largest underwater chamber in the world sinks 663 feet surrounded by cliffs perfect for diving.
• The pink sands of Harbour Island beaches.
• Ardastra Gardens, Zoo and Conservation Centre – home to the famous Caribbean Flamingo.

Every year the Bahamas hosts a range of popular regattas. At the centre of these events are boat racing, good Bahamian food and traditional music. These great celebrations combined with thrilling sailing make the region an attractive destination for cruisers and racers alike.

Closest P&M Port:  Freeport

How can Peters & May help?

Once you have decided on your destination, as a global leader in  yacht shipping , Peters & May can arrange to transport your yacht. Whether you are looking to ship your boat over to the Caribbean ahead of the start of the season, or you have sailed the Atlantic and would like shipping home, Peters & May can provide a seasonal sailing to suit your schedule.

Providing East and Westbound sailings between Europe, USA and the Caribbean region there are numerous destination ports available to choose from. Mast up shipments from the region prove popular every year with some  record-breaking sailings .

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An insider’s sailing guide to the Caribbean

Insider sailing guide, the caribbean, frank ficken, captain of the oyster 65 latitude, has been cruising the caribbean for 25 years. here are his suggestions for the best places to cruise in the caribbean., an insider’s guide to  sailing  the caribbean.

The Caribbean is far more than an island playground. It’s a series of playgrounds, each with its own character. Some sailors spend a week at a time exploring here and there, while others spend entire lifetimes getting to know them all.

Capt. Frank Ficken of the Oyster 65 Latitude isn’t quite at lifetime status yet, but after 25 years of cruising from the Virgin Islands in the northern Caribbean to the Grenadines down south, he has learned a thing or two about the best destinations and experiences.

Here are Ficken’s suggestions for how sailors can enjoy the best of the Caribbean.

SAIL THE DREAM – GET THE INSIDE TRACK FROM ONE OF OUR CHARTER SKIPPERS' LIFETIME OF CARIBBEAN ADVENTURES AS HE SHARES THE MUST-VISIT LOCATIONS, THE GO-TO ISLANDS AND RECOMMENDATIONS FOR THE BEST PLACES TO EAT, DRINK AND SOAK UP THE CARIBBEAN CULTURE.

• THE VIRGIN ISLANDS
• LEEWARD ISLANDS
• WINDWARD ISLANDS

The Virgin Islands

There are three parts of the Virgin Islands: the U.S. Virgins, the British Virgins and the Spanish Virgins. The British Virgins tend to be the busiest, especially for charter boats, followed by the U.S. Virgins and the quieter Spanish Virgins.

“The general concept of the Virgin Islands is that God wanted to sit down and create a place where people could sail and have a great, protected harbour available to them no matter which direction the wind and waves are coming from,” Ficken says. “On any given day, you can decide whether you want to anchor in a hot spot and go to the beach and drink, or cruise five miles to another harbour where you’re one of maybe three boats in a quiet cove. That’s what makes the Virgin Islands special.”

One of the best things about sailing in the British Virgin Islands is that the islands are close together, making for easier navigation than in destinations where the geography is more spread apart. There are numerous ports of entry and exit for these islands, including Road Harbour and West End Harbour on Tortola; Gun Creek in North Sound on Virgin Gorda; Great Harbour on Jost Van Dyke; and Thomas Bay on Virgin Gorda.

Many sailors start at Road Town, which offers the largest natural harbour on the island of Tortola, as well as numerous marinas with transient slips, knowledgeable mechanics and provisioning. There also are some anchorages in this area with mooring fields. Getting there includes sailing up the Sir Francis Drake Passage to the buoys that mark the harbour entrance. Watch for the flashing green buoy that marks a reef on the east side, as well as for the flashing red buoy that warns sailors about Scotch Bank.

For sailors who want to enjoy the throbbing heart of the BVI, Ficken recommends Jost Van Dyke in the British Virgins. It’s home to the Soggy Dollar Bar at White Bay (sailors often swim here, hence the soggy dollars) and Foxy’s at Great Harbour.

“Those are two of the most epic beach bars in the world,” Ficken says. “They’re must-see spots for nightlife, and that includes nightlife during the afternoons.”

Virgin Gorda offers a quieter scene. There, the Bitter End Yacht Club recently reopened, with restaurants, bars, provisioning and water sports, after several years of rebuilding following the devastation of Hurricane Irma. This yacht club is a storied destination for sailors, who have been cruising to the location since 1969. It’s a family-friendly atmosphere that takes its name from the fact that it is “the end of the line” before the Caribbean Sea meets the open Atlantic Ocean.

For an even more subdued cruising ground in the BVI, there is Peter Island, near Norman Island in the British Virgins. The approach into Great Harbour is straightforward, and the southeastern corner offers the best protection from storms. There also is a mooring field to the southwest; it can be a bit choppier, but it offers lovely views of the sunrise.

“Peter Island is more upscale, there’s a very nice resort there, the Peter Island Resort & Spa. There’s a restaurant and a beach bar, but you go there to have a cocktail and enjoy a peaceful, quiet beach.”

In the U.S. Virgin Islands, Ficken is a fan of St. John. While many sailors provision and start an itinerary at the commercial hub of St. Thomas, the island of St. John is far less touristy. Caneel Bay on St. John is usually the sailor’s first stop and there are free mooring balls for transient boats. Some sailors recommend avoiding Cruz Bay as an anchorage because of ferry traffic, but they do take dinghies over to Cruz Bay for a look around town, which has colourful shops full of local arts and crafts.

“It’s a funky, laid-back vibe. Caneel Bay’s restaurant, ZoZo’s, do a fixed-price dinner that gets rave reviews.”

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Leeward Islands

As with the Virgin Islands, the Caribbean’s Leeward Islands each have something different to offer. St. Martin, for instance, is a hub of marinas, services and provisioning. Boats of all shapes and sizes tie up here before or after a Caribbean cruising itinerary.

“That’s a great place to get your boat worked on, to get any service you need. There’s shopping like you would find in America or Europe. You can provision anything you need for the boat or for yourselves. And, they have the international airport.”

St. Martin is actually two islands in one. The French section, known as St. Martin, is to the north while the Dutch section, called St. Maarten, is to the south. While they share an island, the two sections have their own cultures. Marigot is the capital in the French section and is where sailors can clear in. For arrivals in the Dutch section, clearance is at Great Bay or Simpson Bay, with access to the main town of Philipsburg and its commercial centre and shopping.

Once the boat is provisioned, serviced and ready to leave this island, Ficken often sets course for St. Barths. It’s a great destination year-round—the restaurants are world-class and the shopping can compete with Rodeo Drive in Beverly Hills. The main port, Gustavia Harbour, has a first-come, first-served dock for tying up, as well as room in the harbour for about 40 yachts to anchor (depending on how big they are, since sailors and superyachts are often anchoring side-by-side).

The island of St. Barths is especially popular on New Year’s Eve. “New Year’s Eve in Gustavia Harbor is an event not to be missed.

Every major yacht in the world is there. It’s a couple of billion dollars’ worth of boats in one place in the Caribbean and it stretches all along the south coast of the island. It’s the most impressive gathering of yachts that most people will ever see.”

The laid-back counterpoint to that scene is the island of Anguilla, which minimises the number of yachts allowed. Visitors can sink their toes into the pink-sand beaches or spend a night or two ashore in a private villa at Rendezvous Bay. It’s straightforward to sail into this bay but note the location of Shaddock Point on the charts. That’s a shoal to avoid.

“If you want to go, you have to contact one of a handful of agents who process yachts in and out of Anguilla. They charge a fee to do that, but it limits the number of yachts, so you never get overcrowded.”

Not far from there is the island of Antigua and the historic Nelson’s Dockyard at English Harbour where Admiral Horatio Nelson lived in the 1780s.

Nelson’s Dockyard is another spot where cruising sailors can often find themselves docked shoulder-to-shoulder with mega yachts. There are 30 stern-to berths, along with modern services such as shore power, internet and cable TV hookups.

“It is the most historic harbour in the Caribbean. It’s the Caribbean home of Oyster. When someone pulls in aboard an Oyster in Antigua, the people in Nelson’s Dockyard treat them extra special,” says Ficken.

Antigua is also home to the annual Antigua Classic Yacht Regatta, which includes some of the best-known older yachts afloat.

“It’s a phenomenal opportunity for Oyster owners or charter guests to go out with these yachts. One of the races goes out straight toward Guadeloupe and comes back. On either side of that course, there’s a spectator fleet lined up. You see these massive, old, spectacular sailing yachts that were once owned by historical figures.”

Windward Islands

Compared with the Leeward archipelago, the Windwards have far less of what Ficken calls “yachting pressure.” There just aren’t as many boats in the Windwards, so cruising is a quieter, calmer experience.

“The Virgin Islands, St. Martin, Anguilla and even into Antigua—that’s a world where anyone coming from Europe or the United States will be very familiar with what they find,” he says. “When you head to the Windward Islands, you’re going to find something different. Geographically, the islands are huge. Many of them have rainforests. They have a lot less tourism, so when you go ashore, it’s more remote and less developed. You will find real people in real towns. It’s authentic.”

Guadeloupe is one of his favourite islands in the whole of the Caribbean. Specifically, he likes to visit a small island group near there called Les Saintes. Its bay is a horseshoe shape with a sheltered anchorage and about 80 mooring balls.

“It’s the coolest thing,” he says. “Terre-de-Haute is the name of one of the islands, and there’s a small, French village there. If you dinghy in from your boat, you can sit in a small French café. The vibe, sitting there, makes you feel like you’re in a town outside of Paris, but you’re in the Caribbean. There are old French forts that you can hike to. The snorkelling and scuba diving are phenomenal.”

Even more great scuba diving awaits about halfway down the west coast of Guadaloupe, in the Pigeon Islands—where there are a fair number of dive boats, especially during the prime months of December through to May, so sailors need to keep an eye out for scuba flags and people in the water. These islands are a reserve? sometimes called “Réserve Cousteau,” after the famed explorer Jacques Cousteau.

“He proclaimed that it was his favourite place to scuba dive in the world, and it really is phenomenal. It has, in a relatively small area, a wide variety of diving environments. There’s wall diving and there is an area that is very flat with coral that’s great for snorkelling, with a great variety of fish. It has some of the best coral and fish that you will find in the Caribbean.”

Another great island for getting back to nature is Dominica. Most sailors arrive at Roseau, on the island’s southern end, where boats can drop anchor or tie up to a mooring buoy. Another option up at the north end is Portsmouth. Outside of those two main anchorages, anchoring can be difficult on this island because of the steep drop-offs underwater.

But there is much beauty to be seen ashore after the boat is settled in. Part of the island is a UNESCO World Heritage Site and there is a rainforest that is unspoiled for hiking. Sailors who visit Dominica can do river-adventure tours that include rappelling down waterfalls.

“That was one of the best days we’ve had,” Ficken says. “It’s one of the most natural islands.”

St. Lucia, too, has pristine areas. It’s best known for the Pitons—twin volcanic spires that climb more than 2,000 feet skyward. Pitons Bay is the place where most sailors tie up, close to the town of Soufriere. The bay is smack in the middle of the two pitons, so wind gusts can be substantial and there is sometimes a strong current.

Even still, it’s worth watching the weather and cruising in when you have the chance.

“We have spent many happy afternoons and evenings anchored right underneath the Pitons,” he explains. “It’s hard to convey how impressive the Pitons are when you’re on a mooring and you’re 50 or 100 feet off the shore, and they just shoot straight up to the sky. They dominate you. You sit there and watch the sunset.”

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A whole other type of experience can be had at Mustique, an island that everyone should visit because its manicured atmosphere is so different. It's also important to pay attention to the weather here and time your arrival, as big swells can be uncomfortable in the anchorage. But in calm conditions, the location is a stunner, and at the right times of the year, it’s an island that is ideal for people-watching.

“It’s home to Basil’s Bar, one of the most famous bars in the world. Anytime you stop in, there’s a reasonable chance that some celebrity or political figure will be sitting there. The island is popular with that crowd because the island doesn’t get as many tourists.”

At the end of January and into early February, sailors can take in the Mustique Blues Festival.

“They start before the sun sets, so you’re sitting there in Basil’s overlooking the Caribbean sunset, listening to the world’s most famous blues musicians.” “If you happen to be staring out at the water and look to your right, that is the beach where all the fishermen drag their boats up. These are colourfully painted wooden skiffs. You are 75 or 100 feet from them. It is one of the most stunningly beautiful scenes in the Caribbean.”

Farther to the south, Ficken recommends a visit to the Tobago Cays. Many sailors use the approach that has day markers between Mayreau and Baleine Rocks. Be sure to keep the boat between the markers here; sizable coral heads lurk beneath the water’s surface. Also, look for mooring balls. In some parts of these islands, the currents can be strong, so a mooring ball is an easier bet than anchoring out.

All around in the Tobago Cays, wildlife dominates—both above and below the waterline. Sea turtles, colourful fish and coral are all around. There are also local boats that will come calling, offering to sell visiting sailors ice, lobsters, crafts and more. Some of them can help sailors arrange beach barbecues for the whole family.

A lesser-known spot in that same area is Chatham Bay on the west side of Union Island. It’s a quiet anchorage that usually has limited swell. And it’s a location that people will only see if they arrive by boat.

“It has a couple of wonderful beach bars that serve phenomenal, locally cooked food. They’re not at all fancy, but they’re the kind of place that you buy a yacht for,” he says. “Even in the Caribbean, where there’s a lot of sailboats and people visiting, Chatham Bay hasn’t been discovered much yet.”

Discovering all that the Caribbean offers can take sailors a lifetime, and Frank Ficken is on his way! It can also be done during a week of cruising now and then, or during entire seasons spent living on board. No matter how sailors choose to explore this region, memories of all kinds are waiting to be made. That’s the beauty of these islands: Each one offers something just a bit different and special.

A true sailor’s paradise, with over 5,000 stunning islands to visit.

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The Caribbean Yachting Season: Ultimate Guide

Whether you’re an experienced crew member or a newbie eager to set sail, this complete guide will help you chart your course through the Caribbean Yachting Season.

Here I delve deeper into the Yachting Season in the Caribbean, looking at where to go and when, crew agencies, marinas, visa requirements, and big events.

When is the Caribbean Yachting Season?

The Caribbean Yachting season occurs between November and May. This is also known as the Winter Season in Yachting, referring to winter in the Northern Hemisphere.

The timing of this season occurs during these months as this timeframe is outside of the hurricane season.

During the winter months, you can expect to feel slightly cooler temperatures of about 28°C, as well as windy conditions, ideal for sailing enthusiasts.

Main Events to look out for during the Caribbean Yachting Season

If you are hoping to secure a job on a Yacht in the Caribbean, then you are going to want to head over a few weeks before the season starts. This is the time that Yachts are getting ready for the season. Leading up to the season, Yachts may be hiring new crew members or simply needing extra assistance as they get ready.

Another great job opportunity is to position yourself in a location leading up to main events that will attract many yachts to one location:

• The Fort Lauderdale Boat Show (End of October) is an ideal time to find a job on a yacht. After the show, boats start getting ready to head to the Bahamas and the Caribbean.
• The Antigua Boat Show is a 6-day event in the 1 st week of December.
• The St Maarten Heineken Regatta is held in March.
• Christmas and New Year’s Eve. Now these may seem like obvious events to mention, but this is the Caribbean’s busiest time of year. Job seekers should attempt to find work before December, but equally as important is being available in January as many yachts make crew changes for those that didn’t make the cut during the busiest month.

Key Destinations in the Caribbean

The Caribbean consists of thousands of islands, however, there are a few key islands you would want to situate yourself in order to increase your chances of finding a job.

Antigua is a popular destination for yachting activities and a common starting point for most Yacht charters.

The Antigua Boat Show

The Antigua Charter Yacht Show in early December is a popular event for industry professionals and newcomers alike.

The show marks the start of the Caribbean yachting season and attracts impressive luxury yachts in the region. The main purpose of the show is for yacht brokers, vendors, Captains, and the Press to network.

It is an opportunity for yachts to be showcased before the season kicks off, in the hopes of booking charters and impressing charter brokers.

Marinas in Antigua

The 3 most popular marinas in Antigua are conveniently located within walking distance of each other.

• Nelsons Dockyard
• Falmouth Harbour
• Antigua Yacht Club

Crew Housing in Antigua

Crew housing is limited in Antigua so depending on your budget you would need to look into staying at hostels or an Airbnb.

Pineapple House

This Crew House accommodates a maximum of eight guests, dormitory style. Very basic but lovely accommodation located just above the Antigua Yacht Club.

St. Maarten/St. Martin

This island is a hub for Yacht Crew and a strategic location to look for job opportunities during the Caribbean Yachting Season. Its dual nationality means you have access to both the Dutch and French sides.

St. Maartens Key Event

Heineken Regatta (March) : Although the St. Maarten Heineken Regatta is mainly a sailing event, it also draws a significant number of Superyachts and luxury sailboats. Many crew members go to St. Maarten during this period in search of job opportunities.

St Maarten Crew Houses

Smilers Crew House is located in the central area of Cole Bay, making it easily accessible to all marinas. Some are within walking distance, while others are only a few minutes away by bus.

Shrimpy’s Crew Quarters is very basic accommodation ideally located in Marigot. Bookings are through Airbnb.

Marinas in St Maarten

Some of the top marinas to check out in St Maarten are:

• Yacht Club Port de Plaisance
• Isle de Sol Marina
• Palapa Marina
• Simpson Bay Yacht Club Marina

The Bahamas

While the Bahamas may not be officially considered a Caribbean destination, it remains a highly sought-after location during the Caribbean Yachting Season.

Most yachts will travel back and forth between Fort Lauderdale and The Bahamas in between charters. If you are hoping to land a job in the Bahamas, then it would be a good idea to position yourself in Fort Lauderdale or West Palm Beach.

For crew housing options in Fort Lauderdale check out my post on The Top Crew Houses in Fort Lauderdale.

Visa and Passport Requirements for the Caribbean Yachting Season

Many islands offer you a visa upon entry such as the Bahamas, Antigua, and the BVI’s.

If you are planning on starting your search from the USA, then you will need a B1/B2 visa . Even if a vessel flew you into the Caribbean from outside of the USA, that vessel will always make its way back at some point, so it is advisable to have your B1/B2 visa.

If you plan on heading to St Maarten you will need a Schengen visa . The island is split between the French side and the Dutch side. If you are not able to get a multi-entry visa, then your preference would be for the Dutch side of the island.

Crew Agencies in the Caribbean

Most crew agencies will have connections or clients in the Caribbean but their offices are in America or Europe.  

If you have chosen to start your journey into yachting from Florida or West Palm Beach, the top crew agencies you want to sign up for and meet with are:

• Luxury Yacht Placement
• Northrop and Johnson
• The Crew Network
• Hill Robinson
• Cotton Crews

For more detailed information on these agencies check out my post on the Top Fort Lauderdale Crew Agencies .

My Favourite islands to visit during the Caribbean Yachting Season

Whether you are on a Motor Yacht or Sail Boat, these are some of the top islands worth visiting in the Caribbean.

• British Virgin Islands
• US Virgin Islands
• St Kitts and Nevis
• Turks and Caicos

Hi, my name is Lisa, a Chief Stewardess in the yachting industry with 10 years of experience, as well as 8 years of hospitality experience prior to that. Being in the yachting industry has been a whirlwind of adventure, growth, challenges and some of the best experiences of my life, and I am excited to share my knowledge and experiences with all of you.

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Yachting in the Caribbean

Discover more, the yacht set.

We will soon offer a number of cruises around the Caribbean.

Luxury yachts for charter in the Caribbean   allow the most privileged insight into one of the most fascinating and most beautiful corners of the globe. There is no better way to land on a Caribbean island than by sea – no finer way to explore this pocket of glittering oceanic gems than by luxury yacht. Your crew is dedicated to ensuring that your Caribbean vacation exceeds all expectations, promising unparalleled comfort to you and your party whilst catering to your every wish and whim with equal parts professionalism and charm. This truly is what dreams are made of.

Welcome to the most blissful playground on Earth. One of the top cruising destinations in the world, the Caribbean comprises over 7,000 islands, reefs and cays in an area covering more than 2,000 kilometres of sea, reaching from the northerly Bahamas right down to the islands of Trinidad & Tobago off the coast of Venezuela, encompassing the islands of Antigua and Barbuda, St. Bath’s and St. Kitts, St. Vincent and the Grenadines, St. Maarten, and the Virgin Islands, among other delights all within striking distance of one another and navigable by boat. From your advantageous position onboard your super yacht charter, the entire Caribbean region is yours to explore: the world is your oyster. Where will your   Caribbean cruise   take you?

Ever since Christopher Columbus landed on the Caribbean in the fifteenth century, these glorious islands have been ardently fought over across the centuries, and with good reason. With its gleaming white sand beaches and shimmering azure waters, verdant rainforest, warm winds and year-round sunshine, the Caribbean is a true yachting idyll with something to delight explorers of all ages and tastes.

With calm lagoons and schools of tropical fish dancing beneath the surface, the Caribbean is a divers’ and snorkelers’ paradise, offering dozens of captivating wrecks and vibrant reefs to explore, flourishing with colourful marine life Easterly trade winds and plenty of line-of- sight sailing make for pleasant travelling around and between the islands, and the best time to visit is widely thought to be from December to April.

Although the Caribbean is typically known for its secluded white sand beaches with turquoise waters, coconut palms and coral reefs, the truth is that there is so much more to it than this. Each of its islands has its own distinct personality and a rich culture, deriving from an amalgamation of local traditions and colonial heritage. Spend your vacation sampling at leisure from this rich kaleidoscope of tastes, sounds, colours and sights – no island is quite like its neighbour. Immerse yourself in the cosmopolitan culture of St Maarten   and dance all night to calypso music at the Carnival of Antigua; explore the lush cocoa plantations and the vibrant spice markets of   Grenada , then retire to the Virgin Islands for some luxury retail therapy, fine dining and world-class cocktails. Sailing the Caribbean means you can experience all of this and more in one holiday – you truly can have it all with a Caribbean cruise, so why not charter a superyacht   in the Caribbean with THE YACHT SET !

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Yachting in the Caribbean

The Caribbean, turquoise green waters, white sandy beaches, tall elegant coconut trees waving in the gentle breezes. Imagine if this was your everyday view from your ‘office’? Sounds like paradise, doesn’t it? For some people this is their everyday view, at least for part of the year. The busy season for yachting in the Caribbean is from November, after the hurricane season, to July.

For many sailors, yachting is a beautiful adventure.

“It’s free spirited, constant fun and challenging at the same time,” said Josefa Valdez-Telfer.

However, it can only be fun if you have prepared yourself and your boat for any and all situations. Preparing your boat firstly to ensure its sea worthiness and then ensuring that you have your route well charted out. Up to date charts and GPS equipment are some of the tools necessary to ensure your safe passage and arrival at your port of call.

The Grenadines are a favourite port of call for these sailors. These islands cater for the “yachties” by delivering a fresh supply of items like bread, fruits and vegetables to the boat. Sailing is demanding and you have to ensure that you are in the best physical health to face the demands of being out on the ocean. Many “yachties” will agree that this is a favourite port of call. “The yachting industry bends backwards to make you feel at home and do make every effort to ensure your time there is comfortable.”

Leanna, from Go West T&T Yacht, loves yachting and the ease at which they are able to enter ports of call throughout the Caribbean makes the experience even more enjoyable. According to her, “Being processed at customs and immigration is very easy. The officials are very friendly and accommodating and this sets a positive tone for the rest of the trip.” Of great importance to her and other sea lovers is the reduction of non-biodegradable waste. “You can see the efforts being made in the islands to reduce their waste and keep the waters clean.” It is her hope that Trinidad and Tobago would start making bigger strides in the effort to reduce land and sea pollution.

While yachting may be an expensive sport or hobby, many people are willing to invest in it just as others would buy a car or house. For these adventurous spirits, visiting different countries is just more exciting when done by boat. However, for those who would like to sail the open ocean but cannot afford their own boat, websites like www.antlos.com , are cropping up. Antlos is an online marketplace that connects boat owners and holidaymakers. It is similar to Airbnb and Uber . Sites like this provide tremendous benefits for the boat owner and the holiday maker.

The Best Sailing Hot Spots in the Caribbean

Some of the most popular ports of call in the Caribbean are:

* Bahamas – with 700 islands to choose from this is a boating paradise.

* British Virgin Islands – consistent winds and distance between the islands makes this an ideal island hopping destination.

* Grenada and St. Vincent and the Grenadines – Grenada is a good launching point to enjoy the entire Caribbean chain.

* US Virgin Islands – made up of a host of hidden coves and private beaches that you can only get to by water.

* Antigua – this destination hosts one of the most prestigious sailing week in the Caribbean.

* Guadeloupe – many islands to explore especially Les Saintes.

* St. Martin / St. Maarten – two countries one island.

* Puerto Rico – a great place for sport fishing and a stopping off point for people cruising through the Caribbean.

* Turks and Caicos – great diving and snorkeling right off your boat.

* Belize – over 200 islands, beaches and cays to explore.

* Grand Cayman – known for its water sports, diving and fishing.

However, due to changing weather patterns and the damage and destruction caused at some of these traditional ports of call by hurricanes in 2017, islands in the lower Caribbean seem to be capitalizing on this new opportunity. The ABC islands, Aruba, Bonaire and Curacao, are increasing in popularity as ports of call.

No matter your route and destination, your own boat, a yachting charter or a shared yacht, if you have that desire to be on the ocean under the open skies, you can find a way and the Caribbean can be your paradise.

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Sailing the Seas – An Exhilarating Adventure

Immortalising ‘kitch’, the terror of hurricane maria in dominica.

This New Yacht Is Sailing to Gorgeous, Lesser-known Ports in the Caribbean Sea — and I Was on Board With 'Below Deck's' Chef Ben

E merald Cruises' new Emerald Sakara ship brings guests to smaller ports in the Caribbean and Mediterranean, with an onboard marina and the occasional Bravo-lebrity.

With a couple dozen guests looking on, chef Ben Robinson was showing how to slice and dice a fresh red snapper. “You kind of feel him — but you don’t fondle him,” said Robinson, the fan favorite from the Bravo reality show Below Deck, who’s always ready with a quip. As he pulled a perfect filet off the bone, he explained how to salt the fish and that there’s no more important relationship than the one you have with your fishmonger. “My advice is to always be friendly,” he noted. “I like to support my mom-and-pop [businesses]. If you become familiar with them, they’ll say, ‘Hey, I got this in this morning.’”

The cooking demo, which also featured a ceviche how-to and tips on knife sharpening, was one of many “Chef Ben” moments on my trip aboard Emerald Sakara . It’s the newest 100-passenger vessel from Emerald Cruises, which launched in the fall of 2023, a sibling vessel to the Emerald Azzurra .

During an eight-day voyage in March from San Juan, Puerto Rico, to St. John’s, Antigua and Barbuda, the reality personality was definitely one of the star attractions. Robinson spent several evenings in the galley, creating special dishes such as a panko-crusted veal striploin stuffed with pesto.

He also hosted a well-attended Q&A about his life in the kitchen — and spent plenty of time connecting with fans, many of whom booked the trip specifically to chop it up with Below Deck alum.

“We definitely booked because of Ben,” said Shannon Welnel , a Montana-based travel advisor who had lots of praise for his cuisine — and the yacht-like atmosphere on board the 100-passenger ship. Other guests I spoke with admitted they hadn’t seen much Below Deck, but were intrigued by the chance to chill with a Bravo-lebrity.

Emerald Sakara

• With a max of just 100 passengers, Emerald Sakara feels at times like a private yacht, with no lines and no crowds, and outstanding service from a highly experienced crew.
• Minimalist rooms recall the stripped down aesthetic of Miami Beach or Mykonos, Greece, with pops of color from Missoni Home accents and a sleek-yet-functional bathroom with plenty of storage space.
• While this small ship has but one restaurant and one poolside cafe, there’s plenty of choice when it comes to meals, whether you’re hitting the breakfast or lunch buffet or choosing from the dinner menu.
• The onboard marina, which is open in favorable weather conditions, offers watersports and swimming off the stern of the ship.
• Easy to understand and mostly inclusive pricing covers meals, beverages at mealtime, many tours, and surprisingly speedy Wi-Fi.

The intimate-ship vibe was also one reason the chef wanted to hop aboard. “This definitely has more of a yacht vibe than any other [ship] I've been on,” Robinson told me one afternoon. “A hundred passengers is not a lot,” he said. “I've been on boats with 2,500 passengers, and you really do feel like you're anonymous. But here, the service is great, and you really are treated as an individual and someone important. And you kind of lose that on the big boats.”

While Robinson doesn’t have immediate plans to join another Emerald cruise, he told me that there were plenty of parallels between his life on megayachts and what the Sakara offers its guests. “It’s been incredible,” he said.

I had to agree. The Sakara certainly has much to offer, both in spite of its smaller size and because of it. While it’s available to book by the cabin, like any cruise ship, it still manages to feel at times like a private yacht, particularly when it sails to less-commonly visited ports such as Culebra, on Puerto Rico, or St. Bart’s. In the latter, we dropped anchor near Eric Schmidt’s yacht, Whisper , and had the whole day to explore the glitzy island and its capital, Gustavia. (After a drive around in the morning, I managed to catch the beautiful sunset from the lovely little Shell Beach, right in town.)

“The benefit of being on a small cruise ship like this one is that we can enter small ports and areas where others can’t,” said Robert Kuznin, the captain of Sakara , who previously worked with several cruise lines, including Paul Gauguin, Seabourn, and Virgin Voyages. “For example, when we dropped anchor in Esperanza Bay,” he explained about our stop at the island of Vieques, “there were only two meters under the keel — and that was the shallowest I’ve ever been!”

The ability to go places that larger ships can’t was also on display one morning on St. Kitts, one of the final stops of my trip. It was still early in the morning, but already four mega-ships were docked in Basseterre, the island’s capital. Instead of tying up next to them on the busy cruise pier, we dropped anchor just off the beach in South Friar’s Bay, a long sweep of sand in the island’s southern reaches. There were no crowds to contend with, no paperwork hassles, no touts offering dodgy cab rides. A five-minute tender ride to the beach was all it took to meet our local guide. Time from leaving the breakfast buffet to our first stop? About 25 minutes. Even the most efficient mega-ship would struggle to make that happen — and they can’t drop anchor right off the one of the best beaches on the island. 

Other moments aboard Sakara felt like something out of Below Deck . One afternoon, I made my way to the yacht’s marina, a platform at the stern stocked with lounge chairs, refreshments, and water toys such as a floating trampoline and inflatable sea kayaks. I jumped off the stern into the Caribbean and then tried out the ship’s Seabob, a floating gadget that’s like a cross between a Jet Ski and an electric scooter.

As I continued my joy ride, I could see another vessel anchored just north of us. Turns out, it was David Geffen’s private yacht , Rising Sun . Of course, we were there first.

Here’s a closer look at all the amenities of the Emerald Sakara , which sails seasonally in coastal waters in the Caribbean and the Mediterranean Sea.

The Staterooms

Welcome to your starship: the stripped down, white-and-gray cabins on Sakara feel sci-fi chic, particularly when the accent lighting is switched on. They’re also, thankfully, spacious and super functional, with ample storage space (including a safe), a small minibar, a coffee station, and a clever headboard built-in that’s a great spot for your charging devices and water bottle. Most of the 50 rooms and suites have verandas; ocean-view staterooms are the exception. Bathrooms are just big enough, with plenty of storage, and are stocked with Espa products and a hair dryer. My cabin, 421, was a 300-square-foot balcony suite toward the aft of the ship on deck four: I never once heard noise from the surrounding cabins or in the hallway, though I did occasionally notice sounds and vibrations from the vessel, something that is common on even the largest of ships. A note on power plugs: my stateroom had U.S.-style outlets throughout as well as USB-A charging ports on either side of the bed, a nice touch.

Bars and Restaurants

Because Sakara is smaller than most cruise ships, it can’t compete on sheer volume of bars and restaurants. Still, the food on board is solid. La Cucina is the only true dining room, with both indoor and outdoor seating; it has somewhat limited hours compared to the round-the-clock dining options on bigger vessels. That being said, I certainly didn’t go hungry: a breakfast buffet is complemented by traditional à la minute options such as omelets and pancakes; lunch is also buffet style with a carving station. Dinner is more restaurant style, with options from an ever-changing daily menu plus always available classics such as Caesar salad, shrimp cocktail, grilled salmon, and spaghetti bolognese on offer. (Many dietary restrictions and preferences can be accommodated.)

On my voyage, chef Robinson put together several special plates, including what might’ve been the best dish of the week: a sesame-crusted seared yellowfin tuna with celeriac puree. The Below Deck star also put together a panko veal striploin roulade one night and, another evening, offered a citrus-cured hamachi with, in a touch of molecular gastronomy, “mango spheres.” Elsewhere on board, a poolside cafe, Aqua Café, has quick bites like burgers and flatbreads, as well as sweets and coffee pulled from a Cimbali espresso machine. The cocktails served in the Amici Lounge and the Sky Bar were consistently excellent, mixed by a talented team of pros who’ve previously worked on Seabourn ships and in some of Dubai’s top hotels. One weaker spot was the selection of wine on board: pours at mealtimes are included, but they didn’t rock my boat. A short list of “chairman’s wines,” available at extra cost, included a couple by-the-bottle finds such as 2013 vintage Cristal ($650) and some mid-tier Bordeaux and Burgundy options.

Where Emerald Sakara Sails

Though small, this ship isn’t an expedition yacht. Rather, it’s specifically designed for warm-weather coastal cruising, meaning it spends the lion’s share of its time in places such as the Caribbean and, in the Northern Hemisphere’s summer months, the Mediterranean. My trip aboard was spent entirely in the Leeward Islands of the Caribbean, where passages between ports were short and the seas were often calm. (We did occasionally encounter some swells of up to two meters, or 6.6 feet. I saw many guests wearing medicated patches to prevent motion sickness throughout the trip.) Sakara typically spends a season of several months in a given region, with a variety of cruise lengths offered, ranging from six to 24 days. In 2024, the ship will spend April through November in the Mediterranean. Sakara will return to the Caribbean at the end of the year, through April 2025.

Shore Excursions

Tours off the ship were a strong suit for Emerald, at least on my voyage. Most stops offered a variety of activities, ranging from a simple transfer to a nearby beach to a full-on, multi-hour tour. Usually, I found myself ashore with a very small group of folks — fewer than a dozen — and all the guides Emerald arranged were true pros. Passengers raved about a kayak paddle through the bioluminescent bay on Vieques, something I sadly didn’t try myself. I did, however, enjoy a short guided hike on the island of St. John, to the pristine beach along Salomon Bay, which was all but deserted. The organization of excursions felt flawless to me, thanks no doubt to the crew and shore excursion manager, Pilar Atencio. Worth a mention, too, were Atencio’s detailed briefings on what to expect each day. While these sorts of “port talks'' are common on ships of all sizes, they felt particularly useful on Sakara because of how intimate our groups were; many passengers made a point of attending the pre-dinner talks every night, for info on what to expect about our anchorage, historical background on each island, and detailed info about what each tour offering would entail.

Amenities and Entertainment

Call it small but mighty: Sakara has all the essentials, which is a bit of feat for a ship this size. A cozy spa has wellness and beauty treatments, as well as a small hairstyling and facial studio; morning yoga and stretching are available on deck. The fitness center, with a few cardio machines, a Peloton bike, and a variety of weights and other gear gets the job done. The smallish pool and a top-deck whirlpool were lovely — though I spent most of my time in the ocean: the Sakara ’s marina deck is a key feature, and it was open several afternoons during my trip. It’s like the greatest pool party you’ve ever been to, complete with piña coladas, sea kayaks, stand-up paddleboards, and a trampoline, right off the stern of the ship. It is, truly, as much fun as it sounds like, though it is subject to the whims of weather and ocean currents. Also available in some destinations are e-bikes from Gocycle, which are available on a first-come, first-served basis; during my trip, several guests gave them a spin on the island of Vieques. Sakara also carries a ton of snorkeling gear and beach towels, which passengers can borrow whenever they like. In terms of performances, this isn’t the vessel for Broadway-style shows, but guitarist Jamie Ferguson and voyage director Nathalie Millet added plenty of live music to the trip.

Family-friendly Offerings

The youngest passengers I spoke with on my cruise were in their 20s — and they were traveling with their parents. Sakara is perhaps the perfect ship for families traveling with adult children, since it offers such a diverse array of activities to suit different tastes and activity levels, while visiting intriguing destinations. The ship is also intimate enough that everybody can gather easily for meals — or a swim off the stern — without fighting the crowds common on larger vessels. On the other hand, Sakara is probably not the best choice for families with younger children: there’s no kid-specific programming, and you’re likely to be the only ones aboard with little ones. “Emerald Cruises yachts are recommended for people aged 12 and up, and they must be accompanied by and share a cabin with an adult aged 18 or [older],” a spokesperson shared with T+L.

Accessibility

Sakara is probably best described as somewhat accessible: the ship has elevators to all decks and the crew was, on my trip, very accommodating to those with mobility challenges. There are handrails throughout, and bathrooms feature shower grab bars. That being said, several areas of the ship — the outdoor dining terrace, for example — require navigating at least one step even once you’ve reached the deck in question by elevator. “Due to the nature and size of the ships, wheelchairs and scooters are not allowed to be used on board,” a spokesperson told T+L. When the ship is at anchor, it’s only possible to go ashore by tender or Zodiac, both of which could be challenging for those with limited mobility. As Emerald’s FAQ explains: “Guests with limited mobility will require help from a companion, since the crew is limited.” Also of note: many announcements are made only by loudspeaker with no hearing-impaired alternative.

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Memory Making Western Caribbean Family Vacation Ideas

Going wild in roatán my oh my, costa maya crazy for cozumel your perfect day at cococay®.

By Heidi Sarna | Published on March 19, 2024

With pools and restaurants, cruise ships are their own destination. But a cruise on a fabulous kid-friendly ship sailing a Western Caribbean itinerary is a family vacation to remember.

Cruising round-trip from sunny Miami, Icon of the Seas'℠ Western Caribbean itineraries, for example, call at four ports with tons of personality. They're some of the region's best spots for die-hard beach bums, nature lovers and heritage buffs. Embrace the wild side of Roatán's jungles and spectacular coral reefs. Pack your beach bag for a Western Caribbean family vacation to the beautiful stretches of sand that grace Mexico's Costa Maya and Cozumel — or maybe you'd rather lace up your sneakers to climb the ancient Mayan ruins of Kohunlich. At fun-in-the-sun Perfect Day at CocoCay®, it's all about taking full advantage of the beautiful beaches and exciting water sports conveniently offered at Royal Caribbean's private island paradise in The Bahamas. Combine the dazzling new Icon of the Seas℠ with these dazzling destinations for a top kid-friendly vacation.

Going Wild In Roatán

If your idea of having the best family island vacation means a walk on the wild side, Roatán is one of the best places for nature lovers in the Western Caribbean.

At almost 40 miles long, Roatán sports a mountainous backbone surrounded by the world's second-largest barrier reef — the Mesoamerican Barrier Reef system — which means excellent snorkeling and diving are in order. (Go aheaf and tick that off your bucket list!)

Head over to the island's West End and West Bay area, where Roatán's fringing coral reef is just a short swim from the beach. Don your mask and snorkel and float above the labyrinthine reefs to mingle with tropical fish of every imaginable color. It's also likely that you'll see brilliant brain coral, pretty sea fans and other marine life like sea turtles and nurse sharks. Divers will want to head to the West End Marine Reserve at Sandy Bay for some of the world's best diving ,with 38 unique sites, all no more than a 15-minute boat ride away from the shore.

You can also opt for a cruise through Roatán's mangrove trees or hike the verdant heliconia-lined trails of the Gumbalimba Park nature reserve to see (and hear!) the resident macaws and white-faced capuchin monkeys. See this natural wonderland, alive with black spiny-tailed and red iguanas, on solid ground or go for the bird's-eye view on a zipline through the rainforest canopy.

If some of your family members would prefer to dig their toes in the sand, Roatán's soft, white-sand beaches are another great way to spend your day. Head to West Bay and Half Moon Bay to set up camp. There, cool off in the refreshing surf or go for another round of snorkeling along the reef. When you're ready to dry off and explore, check out the restaurants, bars and souvenir shops just steps from your beach towel.

When the hunger pangs hit, try local fare, such as a baleada, a folded tortilla filled with refried beans, crema fresca and crumbled farmer's cheese.

My Oh My, Costa Maya

About 100 miles south of Cozumel, near the fishing village of Mahahual, Costa Maya sits along the Mexico-Belize border. This port offers something for everyone and seamlessly links the past and the present. The best Western Caribbean family vacations are all about choice, and a day in Costa Maya offers it in spades.

History enthusiasts in the family will appreciate the opportunity to explore the ancient Mayan ruins outside of Costa Maya at sites called Kohunlich and Chacchoben, each more than 1,000 years old. Beautifully mysterious, many of the temples and structures have become partially or fully covered in vegetation over the centuries, becoming one with the natural environment. Some ruins appear as mounds of earth (they're underneath) and others have co-mingled with the tangled roots of trees and foliage. One day they might be restored, but there is splendor in their natural state, too.

Kohunlich dates back to the third century; its most notable feature is the pyramid-shaped Temple of the Masks, built to honor the Mayan sun god with a central stairway flanked by large stucco masks.

Similarly, it's believed that by 360 AD, the Chacchoben community was an important destination for ceremonial rituals. Today, you can see remains of the site's Great Plaza and the Gran Basamento, a sacred area where religious rites were once practiced.

Those who prefer living in the moment can check out the stunning undersea life of the very same coral reef that runs along Roatán, Honduras and Belize. It's the second largest in the world after Australia's Great Barrier Reef, and it's easily accessible from the beaches of Costa Maya. Grab a mask and some fins and hop in the water to witness the magic of marine life. There are more than 65 species of stony corals, 350 species of mollusks and some 500 species of fish!

Other colorful underwater sites to explore from Costa Maya include the pristine Banco Chinchorro. A spectacular ring-shaped coral island encircling a lagoon, it's the biggest platform reef system in Mexico and a UNESCO Biosphere Reserve. Another must-see bucket list item for water babies? Taking a dip in the sparkling blue waters of Cenote Azul, a freshwater swimming hole.

When it's time to relax and refuel, head back to the port village of Mahahual for a cold drink. Why not try a refreshing michelada , a spicy beer cocktail? And if lunch is on your mind, the restaurants of Costa Maya's resorts and boutique hotels are reliable spots to sample traditional favorites like cochinita pibil , a delicious slow-roasted pork dish and agua de jamaica , a sweetened hibiscus drink.

Crazy For Cozumel

Marrying heritage with a modern festive vibe, the island of Cozumel promises one of the best family vacation days you can imagine. With something for the whole family to enjoy, Cozumel is a thriving port that makes a Western Caribbean family vacation truly memorable.

If you're set on checking off ancient Mayan temples from your travel list, Cozumel gives you access to several impressive sites. The Mayas lived in the area for 12 centuries and left their mark at the gorgeous walled city of Tulum on the Riviera Maya. Tulum was one of the last cities built and inhabited by the Maya; its heyday was in the 13th to 15th centuries.

Further afield, if you're willing to put in the two-and-a-half hours of travel time. you'll marvel at the spectacular Chichén Itzá, the largest and most fabled of the Yucatán ruins. Founded in 445 AD, the city had about 50,000 residents at its height. By the early 13th century, Chichén Itzá was deserted and relinquished to the surrounding jungle until it was rediscovered in the 19 th  century. Its star relic is the magnificent El Castillo pyramid, which was inspired by the Mayan calendar. There are 365 steps to the top, representing the days in a single solar year.

You might prefer to check out Mayan ruins closer to the port at the small San Gervasio archeological site on the island of Cozumel. This way you'll have more time to hit a powdery white-sand beach. Near the town, you'll find the popular Playa Mia, among the best beaches for families on the Yucatán peninsula, with water sports, slides and lots of dining opportunities.

For snorkeling and swimming, the best spots here are the saltwater lagoon, offshore reefs and underwater caves of Chankanaab Beach Adventure Park.

If your focus is more on drinks and eats, go local and sample Mexican dishes like panucho (fried tortillas stuffed with refried black beans and piled with pulled chicken, tomatoes, pickled red onions, avocado and jalapeño peppers) or pescado frito  (fried fish). Wash it all down with a chilled bottle of cerveza ; you'll find international beer brands alongside local microbrews.

Your Perfect Day At Cococay®

Offering a classic beach day with all the trimmings, Royal Caribbean's family-focused island vacation destination in The Bahamas is a white-sand winner for all ages, from toddlers to teens, mom and dad, and for grandparents, too. Still, there's so much more to do than laze around a dreamy beach all day (though that's not a bad idea!).

Perfect Day at CocoCay® offers many complimentary experiences. Pick your passion: swim in the Oasis Lagoon, the largest freshwater pool in the Caribbean, or watch the kids splash around the water cannons and slides of shipwrecked Captain Jill's Galleon. Grab free beach chairs and umbrellas at the powdery sands of Chill Island℠ and South Beach — two of the best beaches for families in The Bahamas.

For an extra charge, kids and young-at-heart-adults will be grinning ear to ear at CocoCay's Thrill Waterpark® , which has a floating trampoline, a wave pool and 13 crazy waterslides, including the tallest one in North America. For even more adrenaline-fueled fun, whirl across the 1,600-foot-long zipline and try a helium balloon ride for out-of-this-world views.

In between all these adventures, you can fuel up at five complimentary dining venues throughout the island. But if you're craving a day of luxury, then you should head straight for Coco Beach Club® , with its floating cabanas and stunning sea views. The entry fee includes access to a gorgeous infinity pool, an exclusive restaurant and more.

Written By HEIDI SARNA

"Heidi Sarna, a freelance writer who specializes in cruising, is a contributor to Frommer's, Travel Weekly, CNBC.com and The Points Guy, among others. Heidi has taken more than 125 cruises and has visited 78 countries and counting."

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Grenada Prison Escapees Are Charged With Murder of American Couple

The couple, Ralph Hendry and Kathy Brandel, went missing while sailing off the coast of Grenada.

By Aimee Ortiz

Three men who had escaped from a prison in Grenada and were accused of hijacking an American couple’s yacht to flee have been charged with their murder, the police said on Thursday.

The couple, Ralph Hendry, 66, and Kathy Brandel, 71, went missing while sailing off the coast of Grenada . They had been spending the winter cruising in the Caribbean in their catamaran called Simplicity, which was found abandoned in neighboring St. Vincent and the Grenadines on Feb. 21.

There was no indication in the latest police statement that the bodies of the couple had been recovered as of Thursday.

Trevon Robertson, 23; Atiba Stanisclaus, 25; and Ron Mitchell, 30, face two counts of “capital murder by intentionally causing the death of Ralph Hendry and Kathleen Brandel,” the Royal Grenada Police Force said.

The authorities from police forces in Grenada and St. Vincent and the Grenadines have given different ages and name spellings for the escapees.

The men were also charged with escaping lawful custody, housebreaking, robbery and two counts of kidnapping; Mr. Stanisclaus is also facing a rape charge, the police said, but no details were offered on those accusations. The three men made their first court appearance on Thursday, and are due back on March 27. The Royal Grenada Police Force did not immediately respond to a request for comment.

The police had said in a statement released on Feb. 22 that three men who escaped from a prison in Grenada on Feb. 18 and made their way to St. Vincent using a yacht that had been docked in the St. George area of Grenada.

The prisoners were recaptured on Feb. 21, the same day that the couple’s yacht was found. At the time, the police said they were “currently working on leads that suggest that the two occupants of the yacht may have been killed in the process.”

At a news conference on Feb. 26 , Commissioner Don McKenzie of the Royal Grenada Police Force that “information suggests that, while traveling between Grenada and St. Vincent, they disposed of the occupants.”

During a Feb. 26 news conference , Junior Simmons, superintendent of the Royal St. Vincent and the Grenadines Police Force, said the joint investigation into the disappearance with Grenada police was ongoing, and he said the couple was presumed dead.

The investigation revealed that while sailing from Grenada, “the suspects committed several criminal acts including bodily harm to the couple,” he said.

The couple, who were married for 27 years, were “veteran cruisers,” according to the Salty Dawg Sailing Association , a nonprofit that brings together a community of sailors engaged in long-distance cruising on their boats. The couple were longtime members, the organization said in a statement, and “they both contributed to building the S.D.S.A.”

In a joint family statement posted on the association’s website on Feb. 27, Nick Buro, the son of Ms. Brandel, and Bryan Hendry, the son of Mr. Hendry, said that “if we have learned anything from this tragic event, it’s that we know they left this world in a better place than it was before they were born.”

“Ralph and Kathy lived a life that most of us can only dream of,” the message said. “Sailing the eastern coast of the United States, living on their home Simplicity, making friends with everyone they encountered, singing, dancing and laughing with friends and family — that’s who Ralph and Kathy were and that’s how they will be remembered in our hearts.”

Aimee Ortiz is a reporter on the Investigations desk. She was previously a general assignment reporter on the Express Desk. More about Aimee Ortiz