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• Sailing tours and trips
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Small groups, small boats, BIG adventures

Sailing holidays don't have to be an intimidating tangle of ropes, nautical jargon and sea monsters –  not with Intrepid.  Whether you're an old salt with callouses on both hands or you're just getting your sea legs, we've got a sailing trip to suit you. Enjoy cruising around the Phi Phi Islands with the sun on your face, or watch the stars come out over the Aegean Sea with a glass of champagne. Whichever adventure you choose, you can be as involved as you want; help navigate, tack, and steer, or simply kick back on deck with a copy of  Moby Dick  and let the world float by. 

Our sailing tours and trips

Greece sailing adventure: cyclades islands, 10 days from 2414.

See the best of the Cyclades on this 10-day Greece sailing adventure. From Athens to...

Montenegro Sailing Adventure from Dubrovnik

8 days from 2291.

Sail into the sublime waters of Montenegro, departing from Dubrovnik and exploring...

Croatia and Montenegro Sailing Adventure

15 days from 4215.

Experience Croatia and Montenegro’s coastline with this Split to Dubrovnik sail. Find...

Phuket Sailing Adventure

7 days from 1611.

Discover Thailand with this small group sailing trip, from Phuket to Koh Phi Phi. Enjoy...

Sail Greece: Mykonos to Santorini

8 days from 1783.

Embark on a sailing holiday to Greece. Explore the waters, islands, history and cuisine...

Tailor-Made trips

Take four or more on an exclusive trip and tailor your itinerary

Sail Greece: Santorini to Mykonos

8 days from 1386.

Set sail across the Mediterranean exploring Greece's heaven-sent islands. The spoils of...

Greece Sailing Adventure: Corfu to Kefalonia

8 days from 2261.

Take a sailing trip on the Ionian Sea through the waters of Greece. Sail from Corfu to...

Croatia Sailing Adventure: Split to Dubrovnik

8 days from 2306.

A lively restaurant scene, drop-dead gorgeous beaches, lush forests, intricate old...

Sardinia & Corsica Sailing Adventure

8 days from 1774.

Set sail across the clear blue waters of Sardinia and Corsica, exploring the Maddalena...

Amalfi Coast Sailing Adventure

8 days from 2766.

Sail Italy’s Amalfi Coast, exploring the Bay of Naples, Pompeii, Capri, Amalfi and...

Sail Italy: Amalfi to Procida

5 days from 1571.

Explore the Amalfi Coast on board a real yacht on this idyllic small group adventure in...

Sail Ko Phi Phi to Phuket

4 days from 833.

Set sail on Thailand’s waters between Koh Phi Phi and Phuket. Swim in clear blue waters...

Sail Italy: Procida to Amalfi

4 days from 905.

Sail Italy’s Amalfi Coast from the colourful village of Procida, through ancient worlds...

Sail Phuket to Ko Phi Phi

4 days from 882.

Take a Thai sailing tour between Phuket and Ko Phi Phi. Snorkel over a vibrant...

Croatia Sailing Adventure: Dubrovnik to Split

8 days from 1680.

Explore Croatia's beautiful Adriatic coast on this aquatic adventure from Dubrovnik to...

Greece Sailing Adventure: Kefalonia to Corfu

Take a sailing trip on the Ionian Sea through the waters of Greece. Sail from Kefalonia...

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Why choose Intrepid

Experienced skippers 

Our skippers have years of experience sailing the high seas. There’s no one better to show you the ropes (literally).

Best of both worlds

These sailing vacations aren’t confined to the ocean blue. There’s plenty of time scheduled on land to see the sights and check out the local culture.

Safety first, always

 Our yachts are well looked after and regularly maintained and on day one, the captain will also conduct a safety demonstration.

No experience needed

If you'd like to pick up some sailing skills, your skipper can show you how. If not, just relax, kick back on deck and soak up some ocean breezes.

Sustainable travel

We strive to use travel as a force for good. That’s why we choose to give back to the communities we visit, carbon offset all our trips and take our social and environmental responsibilities seriously. We’ve been officially certified as the world’s largest travel B Corp, which means when you choose Intrepid Travel, you can rest assured you’re travelling to improve the planet.

Sailing highlights by country 

Explore the unforgettable islands of Thailand

From the famous landscapes of Phang Nga Bay to the pristine beaches of Koh Phi Phi (and all of the remarkable islands in between), a sailing adventure through southern  Thailand  promises to produce some of your favorite travel memories ever. Relax on golden sand, take a dip in sparkling turquoise waters and cast your eyes upon natural wonders you’ve only ever seen photos of. 

Island hop your way through the Galapagos

There are some destinations in this world that were made for sailing, and the  Galapagos Islands  is one of them. Whether you want to spend your time spotting the islands’ diverse array of wildlife (think spiky marine iguanas and giant turtles) or simply relaxing on the boat with a drink in hand as the Pacific Ocean goes by, a boat tour around the Galapagos is sure to be one for the highlight reel. 

Get lost in the magic of Italy’s coast

Sailing your way down the  Italian  coast is guaranteed to be a unique adventure you’ll never forget, thanks to a variety of stops featuring pastel villages clinging onto rugged cliffsides, scattered ancient ruins from a lost empire, and tantalizingly blue waters you want to get lost in. From wandering through olive groves to laying out on pebbled beaches, cruise the sparkling Mediterranean at your leisure. 

Sail the Adriatic Sea around Croatia

On a trip to  Europe ,  Croatia  is a must-see, but when figuring out how best to explore this Mediterranean country, sailing is the way to go. Whether you want to wander through medieval towns, lose yourself in sparkling blue waters, explore lesser visited treasures or indulge in this epic country’s traditional cuisine, you’ll be in utter paradise from the minute to step foot onto your own private yacht – all aboard! 

In  Europe , we like to go classic. A single-hulled, 50-foot yacht gives you a taste of traditional Mediterranean sailing, not to mention it looks pretty spiffy in pictures too. A typical Intrepid vessel may come with three twin/double cabins, as well as a couple of single berths. You’ll have a recreation lounge, kitchen, three shared bathrooms and plenty of deck space for lazing around and looking fabulous.

When it comes to sailing in  Asia , catamarans are the way to go. They’re smooth, comfortable, and nimble enough to reach those out-of-the-way cays and little island inlets. The twin hull means there’s plenty of space to stretch out –perfect for those balmy evenings and lazy afternoons. Most of the catamarans in our fleet have four twin/double cabins, three shared bathrooms, a galley (that’s nautical talk for kitchen) and a small living area. There are even kayaks and paddleboards for those that want to get a little active (and bean bags on deck for those that don’t!)

Sailing COVID-19 requirements

Sailing faqs, do i have to help sail the boat.

You don’t have to lift a finger if you don’t want to (unless you need to turn the page of your novel or eat a grape). But if you’d like to learn the ropes, that’s fine too. Your expert skipper can teach you everything you’d like to know – from tying knots to unfurling the sails.

How much time is spent off the boat?

There’s about a 30/70 split between land-based and water-based activities on our Asia sailing trips. In Europe this is closer to 50/50 however, some evenings will be spent in port or a marina. Much of this depends on the weather conditions. There are usually at least a few hours each day spent exploring ports, trekking the surrounding areas or relaxing on beaches. Of course, depending on location, there will always be the chance to wine and dine at the local hot spots. 

What will my fellow travelers be like?

We have travelers of all ages and nationalities sailing with us. Approximately 60% of our travelers are flying solo, followed by a mix of friend groups and couples. The minimum age of travelers on our trips is 18, or 15 if accompanied by an adult. We don’t have a maximum age as we believe those choosing a sailing adventure are like-minded regardless of age.

Who decides the rooming configuration?

Your skipper will allocate rooms on arrival to the boat. Single travelers will be paired up with another passenger of the same sex as per the gender marker on their passport, and this may mean sharing a double mattress or twin mattresses side by side.

What are the sleeping arrangements like?

This is our most common question! People are often hesitant about the idea of sharing a double mattress with another traveler of the same sex. Sailing boats tend to be very compact (we use real sailing boats), but the close-quarters nature of this travel is part of the adventure.

Sleeping quarters are designed to utilize the minimum amount of space in order to keep the communal areas as big as possible. In fact, lots of travelers end up sleeping out on deck under the stars, as it’s warm and there’s no air conditioning on a sailing boat.

Our boats have a mix of double, twin (two separate beds or two separate mattresses side by side) and bunks. 

Can I get a cabin to myself?

Single supplements are available on all trips, subject to availability. A single supplement is normally twice the regular price, however, where trips have inclusions such as meals there is a slight reduction in the supplement price. If you are interested in having a single supplement, please contact us to check availability and price.

Do the cabins have ensuites?

On many boats, bathroom facilities are shared, however, some boats have ensuites in each cabin that allow two people to share one bathroom. Our monohull yachts in Europe will have no more than two cabins sharing a bathroom. Most of our catamarans have four cabins and four bathrooms, however, these bathrooms are shared between travelers and crew. Check the Essential Trip Information of your trip for more specific details about your boat. Fresh and hot water is available for showers, and toilets are either electronic or hand-pump.

Will I get seasick?

Seasickness comes in a variety of forms. Common symptoms include fatigue, uneasiness, dizziness, and headaches. The majority of these symptoms usually subside after taking some time to adjust (usually a few hours to a day). Tylenol or Advil can help ease the transition. Heavy seasickness, characterized by vomiting, is uncommon, and it can be treated using medication. There are also a number of other self-management techniques you can try – such as sitting out in the fresh air, drinking ginger tea or watching the horizon. 

For more information about beating seasickness, click here . 

What will I eat?

All Asia and Galapagos Island trips feature an onboard chef who will prepare three delicious meals each day, plus snacks. In Europe, we operate with a trip kitty* (that everyone contributes to) because there’s so much great local produce to taste in each place that it makes a lot of sense to buy food at each stop! This kitty will cover some of your food and beverage costs. On all our trips, there will be an opportunity to enjoy a meal at a local port – we’ll be able to show you where all the good tavernas are. Please check your Essential Trip Information for more specific details.

*See below for information about your trip kitty. 

What about alcoholic drinks?

You are welcome to drink on board - in fact, nothing enhances a sunset more than cold local beer or a glass of wine. Alcohol is BYO (bring your own), so make sure you buy what you need before departure. Some of our boats have alcoholic drinks on board that are available for purchase at local bar prices. Drinking water is free of charge.

How much luggage should I take?

Due to the compact size of the boats and the sometimes rocky nature of a sailing trip, it is advisable that you bring fabric/canvas luggage. It’s a good idea to pack light as there will usually be a gap between the boat and pier. While the skipper or a fellow traveler can give you a helping hand, you’ll need to be able to lift your bag onto the boat.

What should I pack?

Sailing trips are a little different to regular group tours. There’s a finite amount of space on the boat, so it’s best to leave the grand piano, pet llama and foldout four-person mattress at home. The same goes for bulky suitcases, ten pairs of shoes and the surfboard.

This isn’t designed to be a comprehensive packing list, but it’ll get you thinking like a real sailor.   

• A medium-sized fabric bag that can be flattened or stored easily
• A small day pack for shore excursions
• Some sandals or deck shoes that can get wet
• Sunscreen, sunglasses and a hat
• Seasickness tablets (just in case)
• Bathing suit (don’t worry about the snorkel and fins – we provide those)
• Waterproof camera (for those sweet underwater shots)
• A light weatherproof jacket (just in case of high seas or seasonal showers)

For a more detailed packing list, please refer to the Essential Trip Information of your trip. 

What are the arrival and departure times?

These will vary from trip to trip – be sure to check your Essential Trip Information for more specific details. Some sailing trips will head out to sea on the afternoon of the first day. Others will remain in port overnight, however, we still ask that you join the trip at the requested time, as the skipper will need to deliver a welcome and safety briefing before organizing a visit to the supermarket to buy provisions for the trip. All travelers will have an input into the provisions, and this will be purchased from the kitty*.

Please note that due to sailing being a heavily weather-dependent activity, sometimes itineraries may need to change. We recommend allowing an additional night at the beginning and end of the trip to ensure nobody misses any onward flights.

*see ‘What is a kitty’ for more information on your trip kitty.

What is a kitty?

A kitty is a fund or pool of money that all travelers can choose to contribute to at the beginning of a trip. It’s not compulsory however, we’ve found pooling the group's money in one place makes it easier to arrange non-included group meals and tips where necessary. You'll usually eat most breakfasts and some lunches and dinners onboard the boat, so it's best to buy supplies from a nearby supermarket or grocery store at the beginning of each trip. For meals off the boat, our skippers will suggest locally-run restaurants that specialize in local produce and delicacies.  

What is the maximum group size?

The maximum passenger capacity on our boats changes depending on which country you are sailing. Here’s a quick breakdown, but you can always find more specific details in the essential trip information of each tour.

Greece: 11 

Croatia: 8 

Montenegro: 8 

Tips and advice

Aug 18, 2017

5 ways to stop seasickness.

Seasickness is never fun but thankfully it can be treated. Follow these five...

Nov 21, 2018

Everything you need to know about....

Visiting the Croatian islands via sailboat is one of the best travel experiences...

Sep 19, 2017

Your essential guide to sailing jargon.

If you’re just starting to cut your teeth on life at sea, here’s the essential...

Aug 30, 2017

How to protect your camera at sea ....

Nothing's worse than damaging your camera while on the water. Follow these tips...

Stories from the sea

Jun 29, 2023

A day in the life of a greek island....

I grew up surrounded by boats. I spent my summers at a cottage on a lake in Canada...

Jun 06, 2023

Greece vs croatia: where to travel next.

Got visions of the Med dancing in your head?

Apr 03, 2018

What to pack for a sailing adventure....

Croatia was made for sailing, with a gorgeous coastline, delicious Dalmatian...

Oct 15, 2014

Cruising the continent: we reveal....

When sailing in Europe, you have to slap yourself every once in a while to make...

Feb 06, 2020

From business suits to swimming....

“A skipper is more than a profession. You spend so much of your life on the boat,...

Feb 23, 2017

Meet the leaders: judy, bahamas....

This week we're proud to introduce our very first female sailing skipper, Judy....

Looking for more boating adventures?

Adventure Cruising

Ditch the commercial liners for our range of small ship cruises, offering more creature comforts while exploring destinations like Croatia, Greece and Indonesia.

Read more about Adventure Cruising

• Inspiration

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• Ticketed Cruises

Take to the water and fall in love with NYC from the decks of one of our classic yachts. Renowned for our hospitality and our beautiful and elegant yachts - you can find respite, romance and refinement on all our excursions.  Learn more »

Architecture Tours

Join us for a round-island tour of Manhattan with the American Institute of Architects (AIANY) as your guide.  This is the most comprehensive and elegant tour of the New York City skyline today. Learn more »

Private Charters

Host your own private event aboard a classic yacht in New York Harbor.  Office gatherings, client entertainment, weddings, birthdays for 2 to 120 guests across our fleet of 6 elegant USCG certified boats. Learn more »

Classically designed for a contemporary experience….

NYC Architecture Boat Tours»

Join us on an AIANY Around Manhattan Architecture Tour!

NY Harbor Sightseeing Cruises»

Join us aboard one of our classic yachts for a sightseeing cruise perfect for the family!

Solar Eclipse Cruise»

Join us for a magical solar eclipse event in NY Harbor April 8th!

Get out on the water for Spring Break»

Join us on the water for Spring Break! (Statue & Skyline cruises have a super huge discount for kids on them!)

SEE MORE TICKETED EVENTS

Classic Harbor Line: New York City’s Classic Style Charter Boat and Tour Boat Fleet

Dedicated to helping locals and visitors alike enjoy the unique wonders of New York City, Classic Harbor Line hopes for the privilege of escorting you on a relaxing, inspiring, and breathtaking NYC cruise through the waters we proudly call home. Our five classic yachts — the  Schooner  Adirondack  and the  Schooner  America 2.0  (our sailboats),  Luxury Yacht  Manhattan , Yacht  Manhattan II , Yacht  Kingston  and the Yacht Full Moon (our motorized yachts) are reminiscent of the classic boats that cruised the NYC waters in the past two centuries.

Whether buying tickets for one of our New York Harbor sightseeing boat tours to cruise out to see the Statue of Liberty or privately chartering one of our large sailboats or motor yachts for an office outing, you are sure to find yourself on a beautiful boat, surrounded by warm and friendly service, plying through the majestic New York City waterways.

We offer a wide range of ticketed sightseeing boat tours in New York City. Whether you are a fan of cruising on an elegant motor yacht to see the entire New York City skyline with comfort and speed, or if you are inclined to take a more adventurous escape on our swift, double-masted sailboats, you are sure to find a cruise that will suit you with service that treats you like royalty.

We offer a variety of cruises!

NYC Architecture Tours: We collaborate with the American Institute of Architects New York Chapter (AIANY), offering different Architecture sightseeing boat tours around the island of Manhattan. From the original AIANY Around Manhattan Architecture Tour to our brand-new NYC Climate Change Tour, you are sure to learn about the many iconic sights NYC has to offer. Enjoy one of these NYC Harbor cruises aboard our classic-style yachts. Learn More »

NYC Sunset Cruises: Watch the sun set behind the Statue of Liberty on one of our Sunset boat tours. Take in the sun's golden rays as they splash over the skyline of New York City, creating a wonderful collage of colors. These magical NYC sunset harbor tours are aboard our large sailing boats and motor yachts with plenty of space for passengers to move about along with premium customer service. Our NYC Sunset Cruises are relaxing, peaceful, and iconic! Learn More »

NYC Sightseeing Cruise When in NYC, you must do a sightseeing boat tour! Our yachts will bring you to see all of the major iconic sights New York Harbor has to offer. Crowd free, cruise with us in NY Harbor and grab some photos of the Statue of Liberty, One World Trade Center, Ellis Island, Governors Island, the Brooklyn Bridge, and more! Learn More »

NYC Fall Foliage Boat Tour Take to the water and join us for an epic Fall Foliage Boat Tour on the Hudson River. Cruise with us to the Grand Palisades for a sightseeing boat ride to take in the last leaves of fall. This is the perfect leaf-peeping cruise to enjoy a day on the water with friends and family. Don’t miss out on this Hudson River Fall Foliage boat cruise! Learn More »

NYC Holiday Cruises Everyone loves NYC in December! We host holiday shows and cozy sightseeing boat tours aboard our classic boats. Cruise with us on one of our heated yachts decked out in holiday décor and take in the NYC sites of the Statue of Liberty and the New York City skyline. Sit back and relax and enjoy the sounds of holiday jazz music, or grab the family and sing along with us on our Cocoa and Carols Cruise! Learn More »

Private Boat Parties Plan your next private NYC event and rent one of our boats! Our yachts are perfect for any occasion. Enjoy a private boat ride with us into NY Harbor as you and your guests take in the sites and sip on cocktails. Learn More »

Schooner America 2.0 »

Offering our most premium sailing experience in New York City, the Schooner America 2.0 is the newest, largest, and most elegant sailing vessel designed for our operation. Added to the fleet in 2010, America 2.0 offers the most exceptional day sailing one can find in New York Harbor. She is the fastest, most refined, and the most comfortable sailing vessel in our fleet and perfect to sail NYC!

The past meets the future aboard Classic Harbor Line’s Schooner America 2.0 . She is modeled after one of the most famous maritime icons of all time, the winner of the first “America’s Cup” of 1851, Schooner America . The “2.0” aspect of the vessel refers to the eco-friendly aspect of her cutting-edge construction by the designers at Scarano Boat Building, of Albany, New York . Rather than finding a diesel-consuming engine room below decks, you find a large battery bank providing electric propulsion. If you peeled away her hull, you find an extremely durable 3-layered composite of a light wood sandwiching an aluminum honeycomb instead a heavy, all wood vessel built from 100’s of trees. In place of a heavy wooden rig aloft, you find carbon-fiber masts, booms, and gaffs. Together, these strengthening and lightening components of construction help America 2.0 sail effortlessly and with less environmental impact.

From hoisting the sails, to serving beverages, to taking the time to answer your questions about the sights you are viewing, our crew aims for you to leave our boats feeling like you were always in great hands, and having made some new New York friends. We offer public trips for individuals, couples, families, and small groups, as well as private boat charters where you can customize the route, experience, and dining options for your guests.

The Yacht Manhattan & Manhattan II»

For power boat fans, the luxurious Yacht Manhattan & Manhattan II are the real gems amongst the New York Harbor boat tours . They are 1920s style, mahogany-trimmed “commuter” yachts that cruise with far fewer passengers than any other Manhattan sightseeing tour boat. Their ticketed harbor cruises average only about 20-100 guests per cruise. They have two regular routes on their ticketed cruises. One of the most unique is a 2.75 hour cruise that encircles the entire island of Manhattan, passing under 18 different bridges, and stopping briefly at the Statue of Liberty. The shorter 1.5 hour cruise is offered regularly during the afternoon, at sunset, and for stellar city lights cruises. This cruise on the Manhattan and Manhattan II captures all the key waterfront sites of the New York Harbor: the Statue of Liberty, Ellis Island, Battery Park, the Financial District Skyline, the Brooklyn Bridge, the East River and the United Nations Building, along with the numerous other landmarks of the Upper New York Harbor.

All of these cruises include a complimentary beverage from the teak and mahogany bar within the climate-controlled, sky-lit solarium. You can ride indoors or outdoors in absolute luxury and comfort year round. Aside from the yacht Manhattan’s regular ticketed schedule, you can also take advantage of many unique special event cruises. Each year there is a Mother’s Day Brunch Cruise, a Fourth of July Fireworks Cruise, a series of Fall Foliage boat rides up the Hudson River, a Wine Tasting Series, cruises offering specialty tours of New York Harbor, the only Around Manhattan Architecture Tour, and let us not forget a series of “Full Day Cruises” offering full day excursions to destinations on the Hudson River. Also, look for themed cruises to pop up throughout the year in the special events section of this home page.

Schooner Adirondack »

For the sailing enthusiast, a great way to take advantage of the New York Harbor sights is by sailing, aboard the elegant schooner: The Schooner Adirondack , our 80-foot wooden boat sails daily from Chelsea Piers May through November. She most commonly offers 2-hour day sails and sunset sails throughout the day with guaranteed passes by the Statue of Liberty. The Day Sails are perfect for families and guests interested in seeing the sites. These sails will always feature great views of the Lower Manhattan Skyline and Ellis Island, as well as complimentary beer, wine, Champagne and sodas. Wind and tide permitting, you may find yourself encircling Governor’s Island, or doing a short pass up the East River to get up close to the Brooklyn Bridge. Our Sunset Sail on the Adirondack is great for couples or co-workers looking to unwind after work. Another great NY Harbor sail for the romantic couple or a group of friends looking to have a fun night out on the water is the Schooner Adirondack’s City Lights Sail. This sail is truly magnificent and a local favorite. These sunset sails and city lights sails feature complimentary soda, water, beer, wine, and Champagne.

Yacht Kingston »

Yacht full moon », private charters ».

Private Boat Charters in New York City are an extremely popular choice for corporate entertainment or friends and family gatherings. Classic Harbor Line’s Private Events are perfect for 2 to 100 guests. The Boat Charters on the yacht Manhattan & Manhattan II can be accommodated with a wide range of services including full in-house catering, entertainment, and destination-oriented cruises. Please check out our Private Charters page for more information.

*****Tours not taxable, Food and Beverage served aboard are subject to NYS & NYC sales tax which is included in the cruise fares and beverage prices.

JOIN OUR MAILING LIST

Gift certificates, see our calendar of events, private charters.

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

• Private Yacht Charters
• America 2.0
• Manhattan II
• Architecture
• Romantic Sails/Cruises
• Sightseeing Cruise
• Around Manhattan
• Sunset Sails/Cruises
• Holiday Cruises
• Fall Foliage
• Press/Video
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2024 Sailing Season is coming! See you April 13, 2024!

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

Make your sailing experience a memorable one! Sail away with us!

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The Yacht Experience

Discover an experience unlike any other aboard our fleet of superyachts, Evrima , Ilma , and Luminara .

Epicurean Delights

Experience a culinary journey unlike any on land with innovative menus capturing cultural traditions of each port visited.

Luxurious Suites

Designed for the comfort of luxury travelers and each with its own terrace, the yacht's suite experience is unparalleled at sea.

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With nearly as many staff members as guests, our unwavering commitment to service takes to sea.

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Feel at ease in your private oasis at sea, with included service and amenities that set a new standard for luxury travel.

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The onboard spa is the ultimate in relaxation at sea, inviting guests to indulge in scents and delights from around the world.

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Amenities Abound

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Luxury Cruises Aboard

A voyage with The Ritz-Carlton Yacht Collection offers an unprecedented opportunity to be untethered. Here, freedom and flexibility allow immersion in life's exceptional experiences; exploration of earth's exquisite and unexpected hideaways; and stirring of passions and curiosities that create new and deepened connections.

All of this delivered in an intimate setting with a heightened level of care and attention. Enlivened and enlightened, marvel at the beauty of the world through fresh eyes. Live untethered, live fully.

Luxury Caribbean Voyages

The turquoise waters of the Caribbean beckon to sun-drenched islands where history, culture and traditions combine.

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Experience the romantic beauty and history of the Mediterranean Sea's colorful coasts and hidden harbors.

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Sail Yorktown Charters

Yorktown boat tours, va cruises, explore our sail yorktown charters.

• our most popular!
• Sailboat Schooner Alliance II
• Hour Glass 1 hour and 30 minutes
• User All ages

Schooner Alliance II: Yorktown Sightseeing Day Sail

Enjoy a daytime cruise aboard the Tall Ship Alliance II on the York River from the Riverwalk Landing Pier. Immerse yourself in 300 years of history and enjoy the village streets and paths overlooking the York River before you board the ship. Book online!

• Hour Glass 2 hours

Schooner Alliance II: Yorktown Scenic Sunset Sail

Take a scenic sunset cruise aboard the Tall Ship Alliance II on the York River from the Riverwalk Landing Pier. Come aboard and enjoy the evening views of the York River while enjoying a beverage from our ships’ galley.

Yorktown Pirate Ship Adventure Sail

Bring the kids to Captain Mayhem’s School of Piracy and watch them set the sails, steer the schooner, and learn sailor skills! This sail is our kid-friendly cruise, recommended for kids 10 and under. Older kids may prefer Sightseeing Day sail.

July 4th Fireworks Cruise

What could be more patriotic than watching the July 4th Fireworks from a tall ship at Yorktown’s waterfront? This trip departs after the sunset sail and returns after the fireworks.

Explore Our Yorktown Sailing Charters

Yorktown Sailing Charters | Williamsburg Sailing

Set Sail for a By-Gone Era with Yorktown Sailing Charters

Step back into history when you join the crew of the Yorktown Schooner Alliance or Schooner Serenity. Lend a hand at setting sail, take the helm and steer the ship, or look for dolphins and osprey as you glide along the shores of the York River. You will relive sailing’s Golden Age as you cruise past the Victory Monument and Battlefield where our country won its independence. Book your Yorktown cruises online today!

For those who love history, yearn for romance, or have dreamed of a true sailing adventure,

Your Yorktown Ship has just come in!

Setting sail on the historic waters of Yorktown, VA is a magical experience. Let yourself fall into the rich surrounding history and the majestic ship you’re aboard while amongst family and friends – a fresh breeze pulling it all together. It’s our passion at Yorktown Sailing Charters to introduce you to the beauty of the waters we’ve been sailing for over 30 years, give you lifelong memories and keep you coming back for more.

Whether you’re looking for things to do in Williamsburg, VA or searching among the best sailing charters on the Chesapeake Bay, your journey stops with us.

Yorktown Cruises & Sailing Specials

Special events are welcome as we are pleased to offer private sailing charters for weddings, corporate cruises, our own exciting pirate cruises and more. Among the popular pirate cruises you will watch as the kids raise the sails, learn sailors skills and truly experience what it was like years ago aboard a schooner! Catering services and beverages for purchase are available options for your convenience.

For the ultimate enjoyment of a day of sailing come join Yorktown Sailing Charters. After boarding the Schooner Alliance II (48 passengers max) or Schooner Serenity (6 passengers max) you will understand why so many satisfied customers have raved about our sailing cruises for years! We look forward to introducing you to the history, romance and beauty found in and around our boats.

Yorktown Cruise Ships & Sailing Charters Events

Thank you for checking out our website. Continue browsing around for more information on our Chesapeake Bay and Yorktown, VA sailing and boat tours. If you have questions about any of our tours or how you can book a tour, give us a call today at 888-316-6422 or send an email . We look forward to hearing from you and taking you on your next sailing tour!

What Our Customers Have To Say! ★★★★★

Delightful Sail!

A wonderful afternoon with friends sailing out of Yorktown. It was a delightful 90 minutes on the water aboard a two-masted schooner.

Great Experience!

It was our first time visiting Williamsburg Yorktown and Jamestown and the sightseeing sail was definitely something we wanted to do and we were not disappointed. The Captain and crew were very friendly and we learned a lot of history of the area. Overall it was a wonderful time and very relaxing afternoon. Would definitely recommend!

Yorktown Sailing Charter!

We had a great time. Wish there would have been a little more wind. The commentator was very well versed in his local history.

We had a blast!

We thoroughly enjoyed our sunset cruise. The crew was excellent and we especially enjoyed the history lesson. We highly recommend Yorktown Sailing Charters.

It was very informative and fun. Would do it again.it was not crowded like other tours. The crew was very friendly. You definitely get what you pay for.

Buy 3 and get the 4th FREE - Holiday Gift Certificate Special Nov 1-Feb 29!

Santa Cruz Sailing Charters

Offering Daily Cruises

Santa Cruz and Monterey Bay Charters

Public charters.

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Private Charters

Featured tours.

• Most Popular Tour
• Clock Time vary based on season
• User All Ages
• Hour Glass 2 Hours

Sunset Sail in Santa Cruz

Watch the beautiful sunset in a Santa Cruz sailing charter! Enjoy complimentary wine, beer, pizza, soft drinks, and take in the amazing views with family and friends.

Pizza Cruise in Santa Cruz, CA

The afternoon is the most exciting time to be out on the water! Aboard Chardonnay Sailing Charters, enjoy complimentary pizza from Upper Crust, wine, beer, soft drinks, and more.

Learn how to sail at our sister company,

Pacific sail.

The design of the Santa Cruz ’70 sailing yachts is very popular with sailboat racing enthusiasts. Although the hull and sail are designed for speed, the inboard amenities are many, unlike other racing yachts. There is plenty of safe and comfortable topside seating to view the sights and the wildlife of Monterey Bay. Chardonnay Sailing Charters has been able to create a highly-touted experience that caters not only to families, locals, and tourists but to seasoned sailors alike.

Our company is thrilled to be offering the public a genuinely unique experience viewing Santa Cruz and the Monterey Bay Marine Sanctuary from a different perspective.

A SNAPSHOT OF OUR 5-STAR EXPERIENCES ★★★★★

These folks go out of their way to make you feel safe and comfortable during these trying Covid times. I totally felt safe. Then the added fun of just has a great fun crew. We had great weather and water. It also helped of in the distant we whale breaching.

Wonderful crew, Our Orthodontic Team s Doctors went out on the sail as a team-building event. It turned out perfect we had the best time on the water together. I would recommend it for a large or small group. I want to do it again with my family. Highly recommend the sail.

Celebrated my birthday with friends on the BYO night. It was lovely! Vitamin sea, great music, great views, friendly and fun staff! It’s my second time sailing with them and will continue to book with them! It’s great for any occasion!

We had so much fun got to see wildlife. The captain and his crew were awesome. it was a beautiful sunny day. It was safe and kid friendly. The captain let my niece steer the wheel all by herself it was one of her "best day, ever"!

We had so much fun, the weather was perfect and the crew couldn't have been better!! We went for a birthday and were able to spend time together and the kids were excited to "drive" the boat. We will definitely be back again!

• Ticketed Cruises

Take to the water and fall in love with Boston Harbor from the decks of one of our classic vessels . Sailing on a schooner or cruising on a motor yacht you will take in all the sights that Boston has to offer. Learn more »

• Special Events

Join us for a Boston Harbor Sightseeing Boat tour aboard one of our classic yachts. Whether you want a narrated tour or just want to relax on a day sail you are sure to enjoy your time with our most hospitable crew and captains in Boston Harbor. Learn more »

• Private Yacht Charters

Our yachts are classically designed for contemporary experiences.The fleet is historically inspired by turn-of-the-century style yachts designed with classic elements to create and elegant atmosphere for you to host a Nautical Wedding, Corporate Outing, Graduation or Team Building . Learn more »

Classically designed for a contemporary experience….

Boston Harbor Cruises»

Join us for a sightseeing cruise in Boston Harbor!

Sunset Cruises»

Grab your friends and family and join us for a beautiful Sunset Cruise in Boston Harbor!

Boston Brunch Cruise!»

Brunch in style with your friends on the weekend aboard the yacht Northern Lights!

Give the perfect gift»

Give the perfect gift for any occasion this year and gift a Classic Harbor Line Cruise!

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Classic Harbor Line: Boston’s Classic Style Charter Boat and Tour Boat Fleet

At Classic Harbor Line, we are dedicated to providing the most impeccably luxurious and hospitable sailing experience in Boston. Our guests can look forward to the privilege of being escorted on a breathtaking excursion aboard the most elegant sailing vessel in Boston Harbor, the schooner Adirondack III or a relaxing cruise aboard the motor vessel Northern Lights If you are a first time visitor or a seasoned local, an excursion aboard one of Classic Harbor Line’s yachts will provide you with a new perspective on the city of Boston. While aboard our stylish boats, you will be treated to views of the spectacular Boston skyline, historical sites, harbor islands, and perhaps a glimpse of some of our elusive wildlife, such as: the harbor seal. So, come on out and experience the best sightseeing adventure in Boston! And please, kick up your feet because we’ll do all the heavy lifting (and drink pouring)!

There are two ways to cruise or sail with us, you may purchase tickets for one of our public events aboard the schooner Adirondack III or motor yacht Northern Lights or you may privately charter either boat. Tickets aboard our schooner are available for purchase on a Day Sail , Sunset Sail , City Lights Sails , Boston Harbor Island Picnic Sail , or our Sails & Ales featuring Harpoon Brewery . Northern Lights offers tickets on our One-Hour Inner Harbor Cruise and Sunset Cruise .

Consider the schooner Adirondack III or yacht Northern Lights if you are looking for a new and exciting experience to host your next company outing or celebrate a milestone such as: a wedding, anniversary, or birthday. Adirondack III is certified to carry groups of 40 or less, while the yacht Northern Lights is suitable for groups of 149 or fewer. To get more information on privately chartering the schooner Adirondack III or Northern Lights for your next event, go to our Private Charters page . Either way you choose to experience Boston Harbor with us you will be pleased to find our vessels in excellent condition, with comfortable seating, and the most hospitable crew in Beantown.

Classic Harbor Line is known for operating some of the most stunning sailing boats and classic yachts in New York, New York; Newport, Rhode Island; Key West, Florida; and Boston, Massachusetts. In addition to our beautiful vessel, we are also renowned for our excellence in hospitality and customer service.

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Gift certificates, see our calendar of events, private charters.

Sail out from Rowes Wharf and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

• Schooner Adirondack III
• Northern Lights
• Day Sails/Cruises
• Family Friendly
• Food Cruises
• Holiday Cruises
• Romantic Sails/Cruises
• Sightseeing Cruise
• Fireworks Cruises
• Harbor Cruises
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• Our Boston Location
• All Locations
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• Places to Stay in Boston
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• Things to Do in Boston
• General Information: 617-951-2460
• Purchase Tickets Now: 617-951-2460

Copyright © 2024 Classic Harbor Line, 60 Rowes Wharf, Boston, MA 02110 | Powered by Diedrich RPM.

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SV First Light

Set sail with us, philadelphia, pa.

First Light is a luxury 32′ sailboat based in Philadelphia offering private charters, history tours, and sunset cruises.  Our lovingly cared for sleek and modern O’Day 322 is available for up to six guests.  Come and learn about the history of the Delaware river, relax on the water away from the noise of the city with the wind in your sails, or check out the sunset over the city from one of the most unique perspectives available.

We’re excited to bring you the majesty and beauty of the powerful Delaware river and the peace you can experience with just a step off a dock on to our deck.

Ready to sail?

What's included.

Every tour comes with:

• USCG required safety equipment including personal flotation devices for all passengers
• A USCG Licensed captain
• Ice, Soft drinks, and water
• Pre-packaged individual snacks
• Cups, plates, utensils
• A beautiful and unique perspective on the city of Philadelphia

What should I bring?

Always bring a sense of adventure and be ready for fun!  There are some practical considerations though:

• Flat, soft soled shoes (sneakers or sandals)
• Sunglasses, a hat, sunscreen (non spray), and light cover up or jacket
• Camera if you’d like to take photos
• Passengers age 21 and over may BYOB

Sail down the Delaware river during this unique history tour!

Sunset Sail

Golden hour sun glistening off glass skyscrapers and rippling waters…

Private Charter

Sail the Delaware River on a 32′ luxury sailing yacht with a float plan of your own design…

Other Options

Engagement Photos? Marriage Proposals? Gift cards?

Sailing Returns Spring 2024! Click Here and Give the Gift of a Cruise with MBS.

MANHATTAN BY SAIL

Gift a nyc sailing experience, sail nyc and see new perspectives, daily sailboat tours around ny harbor, jazz at sunset on the harbor, celebrate autumn in nyc with fall fest, most popular excursions.

• Users 48 Passengers
• Clock 1 hour & 45 minutes
• User All ages

Sunset Sail - Shearwater

Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantage point of the harbor. The perfect way to kick-start your evening.

• Bestseller!
• Users 134 Passengers
• Clock 1 hour & 30 minutes

Day Sail – Clipper City

Take a step back in time on New York’s only passenger tall ship. Enjoy the sailing experience of a lifetime while taking in the Statue of Liberty, Ellis Island, and more!

Gift Certificates

Are you looking for the perfect gift that combines adventure, romance, and breathtaking views? Look no further! Manhattan by Sail is thrilled to introduce our exclusive Gift Certificates, your golden ticket to a magical sailing experience in the heart of New York City.

at North Cove Marina

The Shearwater is a graceful Newport-style schooner built in 1929, perfect for groups up to 49 passengers . Have your wedding, birthday, or corporate event on board this classic, Gatsby-era sailing ship as she makes her way to the Statue of Liberty and around Manhattan, taking in the sights and sounds of the harbor. If your party is larger than 49, consider our larger boat, the tall ship Clipper City.

CLIPPER CITY

The original Clipper City was built as a cargo schooner in 1854, just prior to the Civil War. Rebuilt and refurbished from the original plans which were borrowed from the Smithsonian Institution, at 158 feet, the Clipper City is an epic venue to host up to 149 guests on a sailing adventure around New York Harbor. Parties and events on our historic tall ships are absolutely breathtaking.

Your Manhattan by Sail Experience Includes

Sailing is About Prevailing.

At Manhattan by Sail, we’re your venue… and so much more. Today, aboard the Shearwater  and  Clipper City , we share the joy of sailing our beautiful harbor with visitors and New Yorkers alike. Offering an incomparable setting for your outing, we’ve developed into a world-class venue. On board during our specialty sails, you can enjoy the sweetness of live jazz music , local craft beers , spicy performances from some of NYC’s premier burlesque performers, and much more. But some things have remained the same since the beginning: our passion, commitment, and our caring, enthusiastic crew who sail each day with their whole hearts.

At Manhattan By Sail, we welcome you aboard to share in our joyful culture and to join us in falling in love with NYC, over and over again.

This is an experience I highly recommend and I'll definitely do again with friends. I booked this for a corporate group outing. It was a great summer Friday excursion with the best view of the city and statue of liberty you won't get on land. Drinks, lite bites, and the Hudson. If you're visiting NYC - Add this to your Things to Do list. If you live in the city, do yourself a favor and experience it in a new way. You'll leave feeling happy to live in such a majestic city.

Absolutely brilliant. Booked the shearwater lady liberty cruise through my New York Explorer pass so wasn't sure what to expect. When we got there was greeted by informative staff and the boat is truly beautiful a restored 1920s schooner. When on board the staff are lovely, gave us blankets and ponchos as it was slightly chilly and the odd spot of rain. Pointed things of interest out to us while on board and kept the great selection of drinks flowing. Brilliant, would recommend.

If you’re going to do a boat trip to see the Statue of Liberty why wouldn’t you choose a historic sailing vessel rather than one of the uninspiring motor boats? Being on a sailing ship with the sails up really adds to the experience. The crew are friendly and engaging and will encourage you to get involved in raising the sails, if you want to.

What a perfect way to enjoy the Upper New York Bay. Great company and both my girlfriend and myself were amazed that all the other boats were so over crowded and ours was perfect. Best way to see the bay and Statue of Liberty. No horrid motor sounds nice music played and drinks on hand friendly staff. Trust us go with this company and you won’t regret it. All the other boats had a frantic experience but ours was heavenly.

Both the ship and the crew were awesome! We especially liked the freedom to move around the entire ship from start to finish. Also not having it narrated turned out to be a plus - it was much nicer to just have informal talks with any of the crew members - they were all very nice and very knowledgeable. They engage volunteers to help and my son really had a great time helping to hoist the sail!

This boat was recommended by some friends & they were spot-on. Loved every aspect of the cruise & enjoyed having a chat with one of the crew members. Had a few cold beers on board too. By far the best value of anything we did in New York, which we found a very expensive city.

Despite being in the nearby area for the past three years this was my first time doing a sail around NYC. I bought tickets on a whim to surprise my boyfriend on a romantic excursion and it was honestly so much fun. The day was really cloudy and cold, but they provide blankets, which is convenient for those who didn’t come prepared. We purchased tickets for the cider tasting/sail, the drinks were good and we were also provided food. The staff were friendly and accommodating and we got really amazing views of the city, I was very happy with our experience.

This has to be the best way to have an enjoyable sail past Statue of Liberty and Ellis Island. You can take the incredibly cost-effective Staten Island ferry which zooms past or the organized and rammed tourist boats from Battery Park, which aren’t much slower. Only the clipper yacht passes closely in a duration which gives everyone plenty of time to stare in amazement and get all the photos you need. Our next visit will be with these guys on another one of their sailing tours. A must-do.

Excellent, relaxing cruise around the harbor including a great view of the Statue of Liberty! The weather was perfect and it was a fantastic way to end a hectic day of traveling. My daughter and I enjoyed wine as we sat on the deck and let the gentle breeze overtake us!

We've been on the Shearwater Brunch Cruise 3 times, & once on the Clipper City Beer/Lobster Roll Cruise. Excellent quality food & beverages, friendly & professional staff. I prefer sailing on the Shearwater since it's smaller & I like the more "intimate" experience. Can't say enough good things about Manhattan by Sail & I can't wait to go on another sail!

The Clipper City schooner cruise should be on every NYC visitor's list! We four travelers took a leisurely, exciting, and informative sail around the Statue of Liberty and can't wait to do it again. The captain and crew were personable, professional, and took excellent care of their passengers. It's also really easy to find. What a great experience and it was my 16 year old grandson's very favorite activity during our July trip! It's tops in customer service, communication, and it's TOPS on my to-do list for our next NYC trip!

A friend of ours suggested we try this and it did not disappoint! We had taken a ferry trip last time we were in New York and I have to say the sail boat is definitely the way to go! The staff were all so friendly and work SO hard. Views of the Statue of Liberty and Manhattan were incredible! A really super experience!

Boarding Locations

North Cove Marina at Brookfield Place New York, NY 10280

GET DIRECTIONS

Pier 17 at 89 South Street New York, NY 10002

The best journey of your life. Tulum, Cancun, Isla Mujeres and Pto. Vallarta.

The only private yacht-experiences company. Set sail, and be amazed. Discover Tulum, Cancun or Pto. Vallarta by sea

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Yacht Private Luxury Experiences

Enjoy an unparalleled experience on board with our unlimited premium bar and the expertise of our onboard chef and host. Our a-la-carte menu is designed to surprise your tastes. Have fun with our water toys, while our top-notch crew ensures that your every need is met with exceptional service.

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Savor experiences we created just for you. Choose your ideal features!

TYE PRIVATE ISLAND

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Riviera Maya / Cancún, / Puerto Vallarta

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Tulum & turtles akumal, isla contoy.

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Set off from the Mexican Caribbean’s best destinations.

Our exclusive, exceptional service will amaze you

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Top-shelf bar with cutting-edge mixology

Menu á la carte, handpicked and market-fresh, prepared onboard by our chef

Luxurious fleet of premium yachts and catamarans

Up to 5 crew members that provide world-class service

Unique secluded beaches and private spots

What our customers say

Discover why we are the Number 1 preferred company in the Mexican Caribbean.

alexandralT5068GK

This yacht trip made my bachelorette weekend! Not only because 12 of my closest friends were there, but the entire Kattu staff was AMAZING! Darwin y Ramon, Ricardo, Sofia, Riqo, and Victor were top notch. They made it so fun, kept the drinks flowing and the food coming (delicious by the way). Hands down would recommend this and especially this crew!!!

494betianac

Increíble experiencia tanto el viaje en el yate cómo practicar snorkel en el arrecife muy muy recomendable ….. la tripulación un diezzzz toda la onda la mejor energía y al servicio de nosotros !!! Volvería mil veces más 🤗💫 el servicio de bebida y comida fue impecable estaban atentos a cada detalle. Hermoso día de disfrute diversión y relax!!! Gracias ☺️

Did the 9 hour tour of El Cielo with YE. The 51’ Leopard was beautiful. Super stable for the long ride and quite fast for a cat. Crew was attentive and professional. Food was gourmet and over the top good. I had 10 people and we had plenty of room. Boat was very clean. Most of my group had never enjoyed a yacht experience. They were blown away!!! Perfect day. Perfect crew. Highly recommend

Nicwoodhouse

Absolutely incredible!! We loved our birthday celebrations on this yacht and had the best time ever! Many thanks to Geremias, Victor, Simon, Octavario & Lola. Amazing team ❤️

ViajeHabana

Una experiencia increíble, es de destacar la profesionalidad y excelente atención de los tripulantes, el Capi Reyes, la hostes Michele, el marinero Jorge y el chef simon!!! Insuperable presentación del yate y el mejor lugar para degustar el riquísimo catering, como así también el lugar elegido para disfrutar el mar!! Superó ampliamente nuestras expectativas

W4760QPalexy

The crew was fantastic. Took care of us all throughout with drinks and the beach destination. Food, food, food... uh-mazing! Drinks-a-flowing and perfect day on the water.

williamwW7046VN

Easily the best part of our trip to the area. Food was delicious, served in a variety of styles, and the drinks were fantastic. Shout to to Christina, Reyes, Erick, and Manuel for curating a date we'll never forget. Can't wait to come back, I hope we have the exact same crew.

I found Yacht Experiences on google when we were staying at a hotel nearby. We had friends coming in to stay and we wanted to surprise them with something fun. When I saw the reviews they had, I requested a boat. I was able to communicate with them through Whatsapp and it was extremely convenient and easy. Everything was up front and pricing and everything was clear. They picked us up from our hotel and brought us to the marina. We were greeted by a full staff on the Wingman with Captain Reyes, Chef Abimel, Bartender Marciel, Hostess Marina, and Colocho! All of them were amazing and professional. Every one of them were there for us constantly asking us if we were ok. Captain Reyes recognized that I looked a little seasick and quickly took us to an area where we anchored away from any waves. It was AMAZING. The food was top notch, much better than even our hotel food. Thank you, Chef Abimel! The drinks were great, thank you Marciel! Marina was constantly watching us to make sure we had everything we needed. Colocho took us snorkeling for a little bit and was very attentive. Colocho was also swimming us out shots of tequila and food to eat on the paddle board! We will definitely come back, and I have recommended them to anyone traveling to the area! Such an amazing experience!

GuillaumeWesterholt

au petit soin pour nous, une attention de tous les instants... Merci au chef Israel qui nous a concocté des plats délicieux (c'était vraiment super bon et surprenant), merci au capitaine Jorge pour la voile et l'attention portée aux enfants, merci à l'accueil et à la bienveillante présence de Christina et merci pour les cocktails de Jorge :-)... Top !

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North America

Central america & caribbean, south america, north africa & middle east.

Few travellers make it to this icy continent, but the lucky ones who do get to explore a frozen Eden ruled by the elements and teeming with wildlife.

G Adventures Land

G adventures sailing & cruises, g adventures private travel.

Whether it’s a family retreat or a girls trip, you can surround yourself with a hand-picked crew and customize a tour that fits you all perfectly.

The Geluxe Collection

Our new line of premium active adventures is officially here. With perfectly paced itineraries, one-of-a-kind accommodations and elevated dining, this is adventure at its finest.

National Geographic Journeys

Go deeper into the cultures and habitats of the places we explore. More is included and you’ll enjoy greater hands-on exploration, interactions with local experts, and freedom to roam.

National Geographic Family Journeys

Are you an adventure-loving family in search of meaningful ways to discover the world together? These tours are specially designed for travellers seven and up and their inquisitive families.

Jane Goodall Collection

Step deeper into the animal kingdom while respecting all of its inhabitants. Our incredible collection of 20 wildlife-focused tours is endorsed by the world-renowned ethologist.

Roamies by Hostelworld

The thrill of adventure. The awesomeness of hostels. Get ‘em both on these immersive small group trips for 18 to 35-year-old travellers.

Why choose us

As the leader in small group travel for 30 years, we know how to do it right: flexible itineraries, freedom to roam, safety, peace of mind, and locally based guides.

Change the world just by having the time of your life. When you travel with us, you become a force for good by acting responsibly and creating positive impact.

Together with our non-profit partner, Planeterra, we ensure local communities touched by our tours benefit from our visits in as many ways possible.

Trees for Days

Leave your destination even greener than you found it! For every day on tour, we’ll plant a tree in your honour and ensure that our forests get to live their best lives.

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Looking to have the time of your life in the next 90 days or so? You can save big if you’re ready to book now.

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The greatest adventures on surf

No matter how far inland we live, there’s something about the sea that calls to us. It’s wide. It’s deep. It’s blue. It’s a canvas upon which we can paint adventures we otherwise can’t do on dry land. Okay, so you probably don’t have your own private yacht waiting to spirit you away to distant shores. But we do. Plenty of ‘em. (And a couple of catamarans, too.) Climb aboard and explore the Greek Islands, the Turquoise Coast, the Adriatic, the Andaman Sea, and other exotic places with a small group of fellow adventurers and a skipper who knows your destination’s every isolated cove, pristine beach, and secluded coastal village. Billions of years ago, we emerged from the sea. Isn’t it time you went back?

Where can I sail with G Adventures?

Canary Islands

Sail for seven days aboard our 15m (52 ft) yacht, with time for hiking, snorkeling and relaxing.

Croatia & Montenegro

Featured sailing posts.

Sri Lanka and the Maldives: A match made in heaven

From the tea and spice scents of Sri Lankan countrysides to snorkelling from 'home' on a dhoni boat

Written by: Pippa Brumwell , 20 Sept. 2022 10:45 a.m.

Cruise through our Insta-worthy European sailing pics

Set a course for your next adventure with inspiration from our Instagram posts featuring Croatia, Greece and Greenland marine adventures

Written by: G Adventures , 10 Feb. 2021 06:21 p.m.

Top 5 moments on the Greek Islands

It’s the place to slow down a fast-paced lifestyle for a while - and what better way is there to soak up the Greek Islands than by sailboat?

Written by: Robin Wu , 11 Sept. 2020 01:53 p.m.

Sail the high seas from your sofa

Join CEO James for a virtual sailing tour of the Greek Islands!

Written by: G Adventures , 3 Sept. 2020 05:12 p.m.

What’s life like at sea?

Adventuresome days.

Squeeze the most adventure out of every port stop. With no fixed itineraries, you’re free to explore on your own terms and at your own pace. Each stop will bring you to great restaurants, scenery, lively entertainment and closer to the culture as it’s lived everyday.

Relaxing nights

By night, our boats anchor in the most beautiful bays and picturesque harbours you’ll find. Sleep in your bunk or camp out on the deck under a blanket of Mediterranean stars. The choice is yours.

Small groups

We believe that small is best when it comes to group size on our yachts, so that you can get the attention and service that you deserve. No more than nine people will be on any boat, including the skipper.

Sample the fabulous fare of the local tavernas, or maximize your travel budget by pooling your cash with your shipmates and preparing your own meals on board.

Celebrating 11 years in Business

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Private New York City Sailing Charters

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Our classic sailboat, named Tara, can accommodate up to a maximum of six people. Tribeca Sailing opened in 2013.  We have the most experience providing the best sailing, boat tours and service in all of NYC. We never charge additional fee’s for a captain or picking up in Manhattan. We also do not charge a booking service fee. The price quoted is the price you pay!

Join us for a two or three-hour private sailing charter of the New York City Harbor. Tribeca Sailing sets sail five times each day, seven days a week.  Feel free to bring any food or drinks onboard our boat.

Where We Go

Sail from North Cove Marina into NY Harbor for unparalleled views of the Freedom Tower, Governors Island, Ellis Island, Brooklyn Bridge and the Statue of Liberty.  This is a boat tour you will remember!

Private Sailing Charters

Staycation and grab your friends for a unique off the beaten path experience.  Celebrate birthdays, anniversaries and other special occasions.  As all of our charters and boat tours are private that means it is just you and your guests on the boat.

The team at Tribeca Sailing prides itself on our awe-inspiring sails and impeccable service and a boat tour for creating memories. Incorporated in 2013 we have the most experience to provide you with the best sailing and service in all of New York City.

Positive Reviews

Rated #2 in all outdoor activities in NYC on TripAdvisor. Winner 2022 Travelers Choice Award.

Sails Per Year

Hurry because we sell out quickly!

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We aim to please!

Tour Options

Including Daytime, Sunset or City Lights private sailing charters and custom sailing lengths.

Classic Sailboat

Our sailboat named Tara is one of only five 1964 Hinckley Custom Pilot 35s.  Tara is the prettiest sailboat in all of New York City.

Your Hosts and our Captains

Captain david.

Captain David learned how to sail at the age of 16 on the south shore of Long Island. David started Tribeca Sailing in 2013 to share his passion for sailing with the world. He fills his sails with facts about New York City, stories about personal experiences, and expert sailing techniques. In short, Captain David wants you to enjoy your boat tour and sail. He is a United States Coast Guard Licensed Master.

Captain Clark

Captain Clark joined Tribeca Sailing’s team this year and has quickly become a valued member.  Captain Clark has an extensive sail training record and a history as a video producer.   He has an extreme passion for sailing and loves to share that passion with our guests.  He is a United States Coast Guard Licensed Master.

Captain Matt

With a sailing resume too long to post, it is fair to say, “What hasn’t Captain Matt done!”.  From offshore experience to captaining large schooners, he has done it all.  We are proud to have Captain Matt on the Tribeca Sailing’s team.  He could work anywhere but loves sailing our boat Tara where he really gets to shine.  He is a United States Coast Guard Licensed Master.

Our Reviews

Our Location

North Cove Marina 225 Liberty Street Corner of Liberty St. & South End Ave.

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Sailing Tours & Trips in Croatia

Get ready to hoist the sails on a sailing adventure of Croatia. Whether you are island hopping or gliding along the coast, with 189 sailing holidays lasting from 4 days up to 17 days, we have made finding the right sailboat tour a breeze! Click here to see all sailing vacations .

189 Sailing trips in Croatia with 1,260 reviews

Dubrovnik – Split, M/S Mama Marija 2024

Sailing Croatia - Split to Dubrovnik

Captain was amazing. Great food and great company Lots of sailing when weather permitted Very well organized

Croatia Sailing Adventure

I had an amazing week on the boat. Ivan was a great tour guide, he felt like a friend and was always willing to help and always up for partying with us! Despite the weather being bad on some of our trip days he still made sure we didn’t miss out on anything. The lunches on board were three courses and consisted mostly of soup to start and stews. The rooms were quite small just to be aware of but there are lots of communal areas where we spent most of our time. You need to bring luggage that can fit under the bed. The boat crew were also great and had banter with us!

Sailing Croatia - Dubrovnik to Split

Great scenery, lovely small group and friendly and helpful skippers. Wonderful holiday with one special moment after another.

CROATIA SAIL - Split to Split (The Dalmatian Voyager)

This was such a beautiful way to see Croatia! Great mix of chill time, swimming, adventuring and activities, and wining, dining and partying together. I went as a solo female traveller and felt very welcomed. The meals catered on board were fantastic (even with a dietary restriction that I have), no complaints!

• €100 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Croatia Sailing Adventure: Dubrovnik to Split

The guide/skipper was great. Informative about where we were going and the plans for each day. All dinner restaurants he took us to, were amazing!! The group was much older than I expected, wanted to travel and meet younger travellers. Price was worth the value of the trip.

Croatia Sailing Adventure: Split to Dubrovnik

Best sailing trip ever! Good captain/guide, great sailing for experienced and beginners, great town/ports stopovers and overnights with incredible sights and food. I loved the night at anchor where we cooked food and had a few drinks under the stars!

Croatia Sail Adventure

Had the best time, trip of a lifetime. Becca was amazing could have asked for any more from her! She was very organised day to day & her proactive approach made the trip flow with ease! It was my first solo trip & having her as the leader made me feel more relaxed.

Pearls of Adriatic cruise

Excellent cruise staff were amazing

Pearls of Adriatic Deluxe cruise

we had wonderful time with our friends on this cruise. we saw some amazing places, Croatia really is beautiful. we loved Hvar and Dubrovnik tour especially. the ship was newly build so we had all the comfort you need.

• Coach / Bus

Croatian islands cruise + Land tour with Plitvice - from Zagreb

First of all I want to thank you for a wonderful vacation. Plitvice Lakes is a must to see place!We loved the ship and the amazing crew. The food especially the fish dishes were excellent. The room/cabin assigned was comfortable and spacious. Recommended trip and company!

5-day Dubrovnik to Split one-way cruise - Classic Plus above-deck, 20-35s

Absolutely Happy to have joined the Tour. Amazing crew and team /group ...heaps of fun and nice chats along the way! Spectecular sea and sights at land. Will do again sometime and can recommend to anyone! Thanks again!

New Croatia One way Deluxe Cruise Split - Dubrovnik

Everyone was friendly, kindness, very professional and excellent service, appreciated for your kind services...recommended !!!

Sail Split to Dubrovnik / Premium Boat, Above Deck Cabins

Andre is one of the best tour leaders I encountered. Andre is professional, nice, humorous and made me at ease from day 1. Split boat tour is one of the most memorable things to do during 2022 Croatia itinerary! This is a place you have heard about in YouTube and now it is your turn to explore it all with fellow travelers which becomes friends. I highly recommend travel tour with Andre.

• €150 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Sail Dubrovnik to Split / Premium Boat, Above Deck Cabins

Croatia is beautiful. The boat has no actually sails. The rooms were small. The food on the boat was decent enough but quite unimpressive. The group was pretty chill but with a positive energy for exploration and adventure. Our guide Missy was always friendly and helpful despite barely knowing a word of Croatian. The crew great although did upset 2 american girls with a culture/personality clash. I liked the country and the people i met but wished i was taking ferries and staying at hostels or hotels.

Croatia Sailing Tour Reviews

Amazing trip, tour guide Dom was sensational, did a very good job at showing us all the landmarks and being an all round good host.

Sailing Tours

• Sailboat (17)
• Motor boat (13)
• Croatian Islands (175)

Regions in Croatia

• Croatian Islands (176)
• Dalmatia (152)
• Kvarner (14)
• Central Croatia (9)

Travel Styles

• 10 Best Sailing Holidays & Trips 2024/2025
• Croatia Travel Guide | All You Need to Know
• Best 7 Day Croatia Itineraries 2024/2025 (with Reviews)

International Versions

• Deutsch: Kroatien Segelreise Rundreisen
• Français: Croatie : Circuits navigation 2024/2025
• Español: Vela Circuitos en Croacia
• Nederlands: Zeilen Rondreizen in Kroatië

10 Incredible San Diego Sailing Tours to Get Your Sailing On

S ometimes we just want to ditch the on-land attractions and head out to the ocean for a sailing adventure. Whether you’ve never been on a boat before or you’re a seasoned sailor yourself but couldn’t get your boat down to San Diego and still need your fix of the sea breeze. Thankfully, plenty of companies offer San Diego sailing tours.

Greg and I got into sailing a few years ago. We currently don’t have our sailing certification but love spending time on the water. So until we can safely maneuver our own sailboat, we either head out with one of our friends (Big shout out to Joe! Thank you!!!) or go on a sailing tour.

Here is a list of our most loved San Diego sailing tours to get you in the mood to hit the San Diego Bay and the Pacific Ocean.

The Best San Diego Sailing Tours

🥇best rated san diego sailing tour.

Don’t have time to read the whole article? Book the highest-rated San Diego Sailing Tour with 380+ ⭐️⭐️⭐️⭐️⭐️ Star ratings on Viator! Book this tour

Small Group San Diego Sunset Sailing Excursion

This three-hour San Diego sunset sail tour brings lovers of the sea out on a Catalina-style sailboat to watch the last of the sun rays fall behind the ocean. The idea of this excursion is to create an intimate feeling, only allowing six guests on board.

There will be beer, soft drinks, and snacks provided by the captain during the ride. Additionally, warm jackets will be on standby in case the wind off the sea becomes too much.

Pass by San Diego’s private marina Point Loma, the USS Midway Museum, and under Coronado Bridge to the island.

The sailing boat has a modern sound system, so if anyone would like to play their favorite songs for some added ambiance, they’re free to do so.

Before you head off, meet at the Sail San Diego Office on Shelter Island. You need to receive a physical paper ticket to board the ship. It will be given to you upon check in.

Sunset Sailing Experience On San Diego Bay

Sunset is, without a doubt, the best time to take a boat out to sea. Watching the dramatic orange colors explode throughout the sky from a top deck is a blissful experience.

Hop on board a classic sailing yacht and make your way down San Diego Bay, catching glimpses of military ships and some of the city’s key sights from a unique perspective.

Take advantage of the many photo opportunities while watching the California sun slowly fades away. As well as an unforgettable sailing experience, you get some white wine, chocolates, soda, and water with your booking.

This fantastic two-hour tour is popular among those looking to celebrate something, e.g., engagement or proposal. This sunset sail in San Diego is one you won’t be soon to forget.

A maximum of six people can reserve a space on the ship which departs from Harbor Island. It’s recommended that you arrive 20 minutes beforehand, so you have time to find the gate. The company is not able to wait for anyone.

Book here San Diego Whale Watching Cruise

Would you like to see some whales? Head out to sea with an expert guide who will provide interesting knowledge about grey whales, dolphins, and other animals that roam around San Diego.

They’ll bring you to several areas where they have spotted whales in the past. This exciting 4.5-hour whale-watching tour takes you aboard a ship modeling a sailing schooner that won a prize at the world’s first America’s Cup sailing competition in 1851. 

This outstanding whale-watching tour includes drinks and snacks, sightings of whales guaranteed, and a no-sickness promise.

Check-in is at the Next Level Sailing office. It opens an hour before departure and closes 30 minutes before. If you’re looking for a small private tour, this isn’t the one for you. The ship can hold up to 77 passengers.

Book here Small Group Afternoon Sailing Excursion

Board a Catalina-style sailboat for six people and embark on a semi-private sailing tour of San Diego.

Get your binoculars ready because you’ll see an array of sights like the San Diego Convention Center, Seaport Village , the USS Midway , and much more.

The boat’s crew members will take good care of you for the duration of the tour, offering complimentary beer, wine, soft drinks, and snacks. If the sun gets too much for you, sunscreen will be on board too. 

Check in for this activity is at the Sail San Diego office. The captain will meet you there and bring you to the ship, where the fun will begin!

San Diego Bay Relaxing Sailing Tour

Step aboard a luxuriously designed Beneteau sailing yacht and cruise around San Diego Bay VIP style. Pop your head inside the spacious cabin kitted out with cushioned seats, soft blankets, pillows, and bean bags to relax on the bow of the boat.

The 2.5 tour starts by taking passengers to catch some gorgeous harbor views of the military ships parked up, including the USS Midway and the Star of India. After, they’ll be taken under the Coronado Bridge to see San Diego Seaport area.

The boat will then venture over the bay to the Naval Air Station and a couple of other notable attractions before making the return to land.

The tour will leave from the Claire Sailing office, only a few minutes from downtown. Beverages are provided by the company, e.g., beer and soda, and passengers can have a shot of driving the boat once given the go-ahead from the captain.

Private Sailing Charter on San Diego Bay

Enjoy a 2.5-hour private sailing charter tour along San Diego Bay.

This is different from other excursions where the company chooses the itinerary. Instead, you decide what you want to see. Whether you want to go whale watching, swimming, or lay an anchor somewhere, the sky is the limit. Additionally, if you’d like the captain to plan your time out carefully, that can be arranged too. See sights like Tijuana , Hotel del Coronado, or Point Loma Lighthouse.

Make sure you arrive outside Clayton’s Galley 10 minutes before departure time. That’s where the captain will meet you beforehand.

Look out for dolphins, sea lions, and whales when you’re out at sea. If it’s the season, you can see them.

Again, this charter sailboat tour of San Diego is private. It will only be your group on the boat with the captain and their team. Snacks and water are included with the tour.

Book here Luxury Catamaran Sailing Charter of San Diego

Take on the San Diego waves on your private catamaran sailing charter that can hold up to 12 passengers.

Set off from the Hyatt Regency Mission Bay for an eight-hour cruise to see exciting attractions like Sunset Cliffs Natural Park , Ocean Beach Pier, La Jolla, and Pacific Beach. Soak up stunning seascapes while trying to spot aquatic animals. The captain can help you out with that one.

The crew on board will be looking after you for the day and will provide five-star, personalized service. This is the perfect tour if you have a big family and want to celebrate fashionably.

Private Luxurious Sailing Cruise in San Diego Bay

This is arguably the fanciest sailing tour you can book in California. It’s a private excursion that tailors to passengers’ needs.

Fancy a sail and swim in Glorietta Bay? Or a romantic cruise along Coronado? Pick where you’d like to see. It’s your three hours. Let the crew do the hard work while you relax, sipping on an ice-cold drink.

The tour is limited to you and 5 other guests. You’ll depart from Harbor Island at 5 pm and have three hours out at sea.

When you see inside this yacht, you won’t want to get off. Its elegant design creates a warm, homey feeling. You’ll forget you’re out on the sea.

The captain and his team are attentive and will look after your group in whatever way they can. To top it all off, alcoholic beverages are included, so grab a beer and watch the sun go down with those you love.

There’s no doubt, this is definitely one of the best sailboat tours in San Diego.

Book here Private Sail Yacht Experience on San Diego Bay

Grab some lovely photographs of San Diego Bay on this two-hour private sailing tour.

Have a 37-foot (11.2 meters) yacht all to yourselves while you kick back with a bottle of champagne, and the captain brings you to see dolphins and other sea creatures along the coast.

The tour is suitable for a maximum of six people and comes with some luxuries such as champagne, white wine, chocolates, and soda. You’re free to bring your own food and drink as well.

Book here Sterling Sails 2-Hour Private Sailing Experience

Did anyone ever tell you that San Diego looks better from the water? See it for yourself on this two hour private sailing experience with your own private yacht and a captain who’s well versed in handling navigation.

Sail all along San Diego Bay, scouting out sea lion hideouts and old military ships like the USS Midway.

The ship can hold six people, making this tour ideal for small families or groups on vacation looking for an ocean escape. Captain Liz will meet your group at the benches beside Marina Cortez 15 minutes before the ship’s sailing time.

San Diego is an amazing place for a sailing tour, with stable winds and a balmy climate; it’s no wonder boating enthusiasts love it here. 

When choosing a sailing tour, you’ll have to ask yourself some questions:

What’s your budget? 

Which attractions would you like to see? 

How much time do you have?

Once you’ve determined this, you’ll be on the boat, ready for your San Diego sailing tour!

Looking for more ideas? Check out these San Diego Whale Watching Tours .

Last Updated on August 2, 2023 by Maria Haase

The post 10 Incredible San Diego Sailing Tours to Get Your Sailing On appeared first on San Diego Explorer .

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Set sail on our fully-inclusive, 7 days skippered SailWeek tours

Party, relax and explore the best European destinations

Party vibe routes

As part of Party & Ultra route in Croatia you’ll explore and party in different locations every day, use your swim stops to reset from the night before. Sail. Party. Repeat. Meet like minded people and become a part of the biggest floating festival in the World.

• Organised parties
• SailWeek Regatta
• Circle & line raft parties
• Extra activities
• Scheduled swim stops

Balanced vibe routes

Dubrovnik (Croatia) and Athens (Greece) routes are perfect choices for sailing holidays. Enjoy spectacular sunsets, white sands, crystal clear waters and beach BBQ party nights. Learn how to sail. Explore ancient coastal towns. Enjoy world famous Mediterranean cuisine and locally handpicked wines.

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• Local cuisine/wine tasting

Pick your destination

Set sail on our fully-inclusive, skippered SailWeek tours where you can experience the best of Croatia and Greece

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Croatia Party Route

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Come live your best life

A trip like no other.

Spend unforgettable 7 days at sea with your crew at your own pace

Active Vacation

Indulge yourself in dozen of parties and activities on your trip

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Traveling solo, with a friend or with the whole crew, we got it all covered

Book a single spot and share a bunk bed cabin with a person of the same gender. We have a lot of single travelers just like you. You’ll be placed on a mixed gender yacht with like minded people of the same age.

Book a cabin or spots on a mixed gender yacht and share your yacht with other spot bookers. Each cabin accommodates two people in shared beds.

All our boats have between 3 and 6 cabins and accommodate 6 to 12 guests excluding the skipper. Host and AC options available.

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NOTE: Only applies to bookings made a minimum of 95 days before the trip. For bookings made within 95 days before the trip, see our Terms and conditions.

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River of Grass Airboat Tours

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Miami, FL 33185

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Enjoy the best private airboat tour in the Florida Everglades with River of Grass. Call us to schedule your adventure today …

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Captain Mike was super great, patient, and informative! We enjoyed our first experience touring the Everglades a s would recommend River of grass airboat tours to our friends! Thanks for a fun filled tour with lots to see!

I had an incredible experience with The River of Grass tour led by Captain Joe. From the start, the communication prior to the tour was exceptional, providing clear and precise instructions for reaching the boat launch. The airboat itself was a standout, impeccably maintained and noticeably cleaner compared to neighboring tour boats. The ease of entry and exit from the boat, along with the comfortable seats equipped with storage space underneath, made the journey even more enjoyable. Captain Joe's thoughtfulness was evident as he provided us with cold bottled water and hearing protection, ensuring our comfort throughout the adventure. As we cruised through the serene grassy glades, Captain Joe's deep understanding of the ecosystem and his passion for the wildlife and flora were truly captivating. His explanations were not only informative but also delivered with an engaging enthusiasm. The boat ride itself was a revelation - remarkably smooth even at high speeds and during those thrilling sliding turns. The encounter with the diverse wildlife was a highlight, with the breathtaking sighting of alligators stealing the show. Observing a mother and her baby gators up close was unforgettable, and meeting the impressive female gator was a surreal experience. Captain Joe's ability to coax her right up to the boat using his calls and splashes allowed us to take stunning photos and savor an extended, intimate encounter with this majestic creature in its natural habitat. I wholeheartedly endorse this company and Captain Joe for their exceptional service. For anyone considering this adventure, I strongly recommend opting for the 2-hour tour - the one-hour option might just leave you wanting more of this awe-inspiring journey into the Everglades' wonders.

See all photos from Eric K. for River of Grass Airboat Tours

Joe was an amazing captain- was informative, polite and educational. He pointed out the eco system and found us some gators too!!

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Yachtapalooza Sets Sail This Weekend, Aiming To Get South Siders Excited About Boating

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EAST SIDE — A day-long open house for local boaters of all experience levels this weekend in East Side aims to be an accessible, fun draw for newbies to the nautical world, organizers said.

Yachtapalooza takes place 8 a.m.-4 p.m. Saturday at Crowley’s Yacht Yard , 3434 E. 95th St.

The free, indoor event celebrates its 25th anniversary this year. It features free seminars and demonstrations, a pig roast, live music, a flea market Friday and Saturday and a three-day sale on nautical items from Boater’s Closet Friday-Sunday.

Organizers hope to draw 1,000 current and future mariners out to this year’s event, said Nick Fugate, sales manager at Crowley’s Yacht Yard.

Yachtapalooza will also include a boat showcase by Nautical Donations , Crowley’s charitable arm, featuring several rehabbed, budget-friendly boats for sale.

Proceeds from the boat sales will support nonprofits like the Chicago Maritime Society and the Judd Goldman Adaptive Sailing Foundation, Fugate said.

The Chicago Boat Show dropped its sailing portion in recent years and is planning a move to the suburbs next year , so this weekend “is probably the closest thing to a sailboat show that we’ve got in Chicago,” said Charles Szymanski, a Yachtapalooza organizer and president of the nonprofit Rainbow Races .

With a few dozen vendors and free seminars on topics like marine pumps and toilets, splicing line and rope, and applying epoxy and varnish, Yachtapalooza offers “anything you would need” to maintain a boat, Fugate said.

The seminars give attendees “the chance to use the products, put their hands on them and feel them, and learn a little more than watching a powerpoint on a screen,” he said.

The event is “the perfect opportunity for anyone looking to get into sailing, [with] questions about sailing or [wanting] to check out a sailboat for the first time,” Szymanski said.

Rainbow Races is one of Yachtapalooza’s featured vendors, and its members will host one of the day’s seminars. The group aims to erase barriers marginalized groups may face in getting into sailing, Szymanski said.

It’s the only U.S. Sailing-sanctioned, LGBTQ+ sailing school in the country, and the only LGBTQ+ sailing organization in the Midwest, he said.

Rainbow Races’ first day of sailing school begins May 18. The group is offering a $50 early-bird discount on sailing classes through the end of April with the discount code “hydra50.” To register, click here .

The sailing world struggles with homophobia, misogyny, elitism and other forms of discrimination prevalent in other sports, Szymanski said. Rainbow Races creates a safe community around the sport which tries to counter those problems, he said.

Despite its issues, due to the collaborative nature of sailing, it’s also “probably the most friendly sports arena I’ve experienced,” Szymanski said.

“Sailing is a true team sport,” he said. “You have to trust your crewmates with your life, and you also have to support each other.

“Sailors are aware if we don’t evolve, we die … If the wind changes, you have to change with it.”

Chicago’s sailing community is robust, particularly with groups like the Park District, local yacht clubs and Rainbow Races encouraging new people to explore the sport, Fugate said.

But with a massive lake as Chicago’s backyard and “a very strong maritime history” in the city, the community could definitely stand to grow, Szymanski said.

Yachtapalooza is a free “casual meeting of the minds” that can help spread the joy of sailing and boating and change a misperception that the community is only for the ultra-rich, Szymanski said.

Million-dollar yachts “are great to look at and to dream about, but when you get down to it, Chicago is a blue-collar city,” Szymanski said. “A lot of the folks trying to buy boats are probably younger and more [budget-conscious]. It makes this a really unique opportunity to bring people in, in a very casual, unencumbered way.”

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