Yacht Charters

Sailing the Caribbean

One of the most popular activities in the Caribbean is sailing.

Because the winds are so consistent and the weather is rarely less than beautiful, this is a very safe sport so it is open to novices and experts alike.

Browse through the links below to find the sailing experience to suit your level of expertise and your pocketbook.

The sailing resources on this page are mainly for those businesses based in the islands.

St. John Yacht Charters
Sailing from St. John

Not all St John day-sail boats provide a snorkel guide. We are very knowledgeable of the surrounding area snorkel sites, their flora, and fauna and can be your guide while you're in the water.

For our Sunset sail and half day trip we have a minimum of 4 people. If you are in a group of 2 we usually can find 2 more to make the trip happen. Bring your I-pod, make a play list, and we can plug it in.

In the past a birth certificate and photo ID were enough to travel to the Jost Van Dyke in the B.V.I.

Well, the rules have changed and now a passport is needed to travel to the B.V.I. Call us for information about multiple day term charters.

CarTrawler possibly has the best prices
for Car Rentals...read more

Sail BilindaSail Bilinda
Sailing St Croix

Bilinda Charters specializes in private sails - the most popular being our Half Day Sail. Just let us know what you want your day to consist of, whether it's snorkeling, a swim with the tarpon or simply enjoying the calm waters off St. Croix. Enjoy sailing as much or as little as you'd like.

Take the helm yourself or relax and let the captain do the work.

The crew on Bilinda Charters is here to ensure you have a fun, safe, relaxing trip. We will cater to all your needs and will strive to make your sailing experience the best part of your vacation on St. Croix. A sailing charter is perfect for couples, families, a group of friends, or a company outing. People of all ages will love the experience.

Sail Bilinda operates within the boundaries of the East End Marine Park. The Park encompasses a mosaic of fringe reefs, mangrove forests, sea grass beds and nesting sites for endangered sea turtles.

Within the crystal waters, sunshine illuminates coral monuments and rainbow colored fish, hidden just beneath the surface.

Barbados SailingBarbados Sailing
Sailing Barbados

Ah, Island Life. We want to introduce you to our way of life. This is where we come in. Come sail with us and enjoy our fully equipped catamarans. Our flagship Why Not says it all.

After we have wined and dined you on our fine Barbadian Cuisine, we will take you snorkeling in our crystal clear waters where you will see the most colourful and friendly tropical fish or, swim with our local sea turtles.

When you are totally relaxed and fully into the "island life", let us cruise you down our west coast while you lie in the sun or just relax in the shade, cooled by the gentle Windward breezes while listening to the pulsating rhythms of our Caribbean music.

Puerto Rico SnorkelingExciting Sail and Snorkel excursions in Puerto Rico
Sailing Puerto Rico

 Join us aboard the beautiful sailing catamaran, Spread Eagle.

Explore white sand beaches or go snorkeling the crystal clear Caribbean waters and reefs.

Our sailing and snorkeling tours include sumptuous buffets, complimentary drinks and each guest receives a free snorkel.

Sea Spray CruisesSea Spray Cruises
St. Lucia

Step aboard Liana's Ransom for a swashbuckling adventure down St. Lucia's stunning West Coast. Sea Spray Cruises is one of St. Lucia's leading tour operators, and our Pirate Adventure promises the ultimate in excitement for the whole family.

Join Captain Wello and his crew of buccaneers as we first sail south to the picturesque town of Soufriere, then visit waterfalls, explore botanical gardens, witness the world's only drive-in volcano, hunt for treasure and fire the rigged schooner's cannons.

Drinks and lunch are included, and special Pirate Kits are available for purchase. Come see why children and adults alike call the Pirate Adventure 'a blast', "the best trip ever" and "excellent - 10/10."

Sailing Anguilla

The Anguilla Sailing Association - The Anguilla Sailing Association is resident on the beautiful island of Anguilla, the northern-most of the Leeward Islands.

Located just 8 miles north of the island of St. Martin/Sint Maarten, Anguilla offers some of the best sailing waters in the Northern Caribbean.

Sailing Anegada (BVI)

Spirit of Anegada - The British Virgin Islands (BVI) is one of the classic Caribbean yacht charter vacation areas and a great place for a sailing or motor boat vacation. If you like cruising to safe and beautiful anchorages surrounded by lovely waterside restaurants, then the British Virgin Islands is where to find it.

Sailing Antigua & Barbuda

Antigua & Barbuda Marine Association - The first Caribbean charter businesses were set up in Antigua in the early 1960's which came about as a result of Antigua being the ideal destination for trans-Atlantic sailors.

Caribbean Luxury Yacht Charters - We specialize in fully crewed yacht charters and can help you choose the most perfect Caribbean yachting vacation.

Ondeck Ocean Racing - From our base in Falmouth Harbour, we offer you a variety sailing experiences suitable for everyone from 8 to 80+.

Sailing from Aruba

Mi Dushi Sailing Adventures - Built in Sweden in 1925 of oak and mahogany this 80 Ft. windward vessel is one of the last great authentic sailing ships still operating in the Caribbean.

Morning Star - Enjoy a leisurely guided snorkel with the friendly marine life, work on your tan or enjoy a Five course gourmet meal on our sunset cruise. Your options are limited only by your imagination! All of our cruises are tailored to your desires.

Octopus Sailing Cruises - Captain Jethro Gesterkamp and his First Mate Jeff have been initiating delighted visitors to snorkeling and the relaxation of multi-hull sailing for over 25 years, the last 18 with Jethro's 40 ft trimaran sailboat, The Octopus.

Red Sail Aruba - What spot in Aruba offers a stunning view of Palm Beach from the open water? It's Red Sail Sports' fleet of three luxury catamarans. These custom-built vessels offer daily cruises along Palm Beach for snorkeling, sunset and dinner sails.

Tranquilo - Aruba's best family operated sail and snorkel cruises since 1977. Tranquilo was founded by Capt. Mike Hagedoorn, then carried on by his son, Anthony. He makes sure safety and personal attention are top priorities.

Wave Dancer Cruises - Enjoy the freedom of sailing and discover the thrill of Aruba's constant & soothing trade winds. Our Multi-Hull Yacht design offers you a smooth & stable ride. While you lounge on our spacious decks, experience our gracious hospitality and friendly Captain & Crew whose prime concern is your safety & comfort.

Sailing in the Bahamas

Amarok Sailing Charters - Take a captained sailing charter with Angela and Joe aboard the sailing yacht Amarok. Embark from Nassau, Bahamas from mid-December through early June for a sailing cruise to the Outislands of Exuma, Eleuthera and the Berry Islands.

Blackbeard's Cruises - Blackbeard's Cruises offers live-aboard scuba diving adventure travel vacations to the Out Islands of the Bahamas. Reef, wreck, wall, drift, night and shark dives are offered on each trip.

Blue Water Sailing School - Serious training for cruising sailors, and those who want to be.

Cat Ppalu Cruises - The Liveaboard charter yacht Cat Ppalu, offers scuba diving, snorkeling, sailing and adventure cruises. Each week we set sail from Nassau to the Exuma Islands on the 65' sailing catamaran, Cat Ppalu. This is the ultimate escape aboard your own private yacht.

Sailing Barbados

Action Charters - We provide that fun-filled Pirates of the Caribbean experience that will make your holiday extra special.

Barbados Sailing Association - The Bardados Sailing Association is the governing body of sailing in Barbados.

Cool Runnings - Welcome to Cool Runnings Catamaran Cruises, voted 2nd Most Popular Attraction by the globally recognised Zagat Survey as 'the Rolls-Royce of catamaran excursions' in Barbados.

El Tigre Sailing Cruises - Designed and built by one of the World's top Catamaran Designers, our 60 foot catamaran will excite the sailor with her exhilarating performance while soothing the timid with her stability and comfort.

Good Times Catamaran Cruises - We offer private charters (including crew) or various day cruises for groups up to 16 persons.

Sailing Barbados - After we have wined and dined you on our fine Barbadian Cuisine, we will take you snorkeling in our crystal clear waters where you will see the most colourful and friendly tropical fish or, swim with our local sea turtles.

Sailing Bermuda

Bermuda Charters - AJ's Wings is one of Bermuda's newest charter yachts and is captained by Anthony Mello, a prominent Bermuda captain with over 4 decades of seafaring experience, including countless Atlantic crossings.

Bermuda Windsail Charters - Our yachts are owner operated and maintained to a high standard. We arrange sailing regattas for convention groups visiting Bermuda. We can also book up to 10 other yachts to carry groups of up to 200 people for regattas or any other water based activities.

Bermuda Sailing Association - The Byte Class of Bermuda (BCOB) in conjunction with the Bermuda Sailing Association (BSA) has begun an intensive training program with the goal of making Bermuda a force in the Olympic sailing arena once again.

Sailing Bequia

Blue Star Yacht Charters - Escape with us on our fantastic 50ft Beneteau yacht, Polair Star, sailing through the Caribbean with your very own Captain.

Caribbean Schooner - Enjoy a day of sailing aboard the 100 ft. Friendship Rose.

Grenadine Escape - Visit Breath-taking islands like Mustique, Canouan, Bequia and Barbados. We have intimate knowledge on Villas Rentals, Yacht Charter and Real Estate deals.

Sail Relax Explore - Sail Relax explore will provide a full listing of available yachts.

Sailing the Cayman Islands

Cayman Islands Sailing Club - The National Sailing Centre is located at the Cayman Islands Sailing Club. Its purpose is to promote sailing and sailboat racing to all people in the Cayman Islands.

We offer sailing lessons, rentals, and camps for residents, visitors, and members of the Sailing Club and coaching and training for national team athletes. All lessons are taught by internationally certified instructors and coaches on dinghies and keelboats.

Red Baron Charters - Sailboats and Powerboats

Red Sail Cayman - What spot in Grand Cayman offers a stunning view of the island from the open water? It's Red Sail Sports' fleet of four luxury catamarans. These four custom- built vessels offer daily Snorkel Sails to Stingray City, Sunset and Dinner Sails.

Stingray Sailing - Once you have made a booking with us, we will take care of everything that is needed for you to enjoy a day swimming with the rays. We will meet you at the cruise ship dock, provide transportation to and from the our boat, provide you with snorkel gear and instruction. We then take you out to the sandbar and the reef, on our spacious forty-three-foot sailing catamaran, to swim with the stingrays.

Sailing Curacao

Sail Curacao - This sailing experience is for people who want to enjoy the Caribbean in the luxury of their own private yacht, complete with excellent food and tailored to each group.

Bounty Adventures - Whatever trip you choose from our tropical menu, you'll board an unforgettable experience, which includes our unmatched cuisine and fully stocked open bar.

Insulinde Sailing Ship - Whether you are celebrating your birthday in a big way, or impressing your best clients with an original networking reception, Sailing Ship Insulinde makes sure that you and your guests have a great day.

Sailing the Dominican Republic

Carib Wind - Cabarete, world famous for windsurfing and kite surfing is now ready for Laser sailors.

Sailing Jamaica

Sailing Jamaica Freestyle Experience - Sail the Clear Blue Waters of the Caribbean an enjoy your sailing experience to the fullest. It will be just the way you want it. Celebrate sailing with lots of music and dancing. We offer a Wet & Wild Sail and Snorkel Trip or Relaxing Sunset Tour. Music along with catering for Bar and Food is available.

Sailing Puerto Rico

Erin Go Bragh Charters - Erin Go Bragh Charters offers personalized day, overnight and longer term-charters to the lovely Caribbean Spanish (Puerto Rico, Vieques, Culebra), U.S. and British Virgin Islands aboard our beautiful 50-foot Gulfstar Ketch the Erin Go Bragh III.

Ventajero Sailing Adventures - Enjoy sailing the beautiful waters of Fajardo, Puerto Rico and its beautiful secluded islands on the Ventajero 4. A 52 ft. charter sailing vessel with all the beauty, comfort and attention you would only dream to experience on your visit to our island.

 Sailing St Croix (USVI)

Jones Maritime Company - Jones Maritime Company has a US Sailing Certified Sailing School in Downtown Christiansted, St. Croix, US Virgin Islands.

Sailing St John (USVI)

Cruz Bay Watersports - Island Spirit has two swim ladders, bow and stern with warm water showers, a fun waterslide for kids of all ages, and two restrooms. The cabin features a large U-shaped bar for beverage and food service, upholstered seating in both sun or shaded areas, and stereo throughout the vessel, making Island Spirit an extremely comfortable and fun yacht to sail on.

Outlaw - Sail farther and faster with Paul and Vicki on St John's largest and most comfortable charter yacht Outlaw. Let us introduce you to a level of sailing that you have never experienced before. Our Baltic 55 is U.S. Coast Guard certified for your group of up to 12.

Sail Safaris - Our sailing tours are like nothing you've ever experienced before. We are focused on getting off the beaten track. We go to hidden beaches, uninhabited islands and vibrant coral reef. So bring your snorkel gear, an appetite for adventure and dress to get wet.

Sail St. John - Offering day, half-day, sunset sails, private charters, motor excursions, weddings-on-board and a variety of other on the and in the water activities for Caneel Bay Resort and St. John guests.

Sailing St Lucia

Destination St Lucia - Conveniently located within Rodney Bay Marina in St Lucia, DSL Yachting is your ideal takeoff point for a sail through the Caribbean Windward Islands. Destination St. Lucia Yachting was founded in 1991 by Ulrich and Sandra Meixner, two Austrian sailing enthusiasts. The DSL charter fleet is small enough to be meticulously maintained while still giving the customer a good selection.

Sailing St Maarten/St Martin

Any Way Marine - A small fleet of boat is available for day charters. We offer bare boating and crewed vessels at very attracting prices. All the boats have been bought for personal use so they offer the best equipment and are rigged for comfort.

Celine - Celine is a 40 ft catamaran built in South Africa by her Captain Neil Roebert. She goes out for daily cruises and conducts a glorious Sunset Cruise around the lagoon on Thursdays. Three times a week she goes out for a Pub Crawl, visiting three popular bars in Simpson Bay to sample their food and drink and affording seldom seen views from the water. Celine also does birthday parties, weddings and private charters.

Eagle Tours - Eagle Tours is a charter company located on the Dutch side of the Caribbean island of St. Maarten. With great facilities and fantastic crew on all the vessels, the tours are a fun and enjoyable way to see a side of the island that most visitors would miss.

Island Water World - Island Water World is a chain of marine stores serving Caribbean sailors and water sports enthusiasts for over forty years. We carry a wide range of quality products from boats and motors, anchoring and docking equipment, sail and deck hardware, general maintenance, onboard comfort, marine electronics, navigation and safety gear to general marine chandlery.

Sailing St Thomas (USVI)

Blue Tang Yacht Charters - Come aboard the Blue Tang and experience a day of luxury and adventure. Island-hop with our certified captain and experienced crew while enjoying great food, snorkeling, and a yacht full of fun.

Captain Max - Join the famous Captain Max on the S/V Lou for an unforgettable day of sailing, snorkeling and fun on St. John and the surrounding islands. S/V Lou sails with a maximum of six guests. Private parties always welcome. She has a full bar and a fantastic Mediterranean lunch. Come for the sailing and stay for the laughter.

Day Sail Fantasy - Voted #1 Daysail on St. Thomas by The Virgin Islands Daily News. Cruise Ship guests take a short 15 minute cab ride (tour) of our beautiful Island to St. Thomas' east end marinas, shops, and gateway to the protected waters of St. John and the British Virgin Islands. St. John guests take a short 15 minute ferry ride across Pillsbury Sound to Red Hook, St. Thomas. Enjoy the many great shops, restaurants, and ice cream parlor in Red Hook after the sail.

Fury Charters - Experience the Caribbean like you never have before. Whether you are staying on St. Thomas, or coming to us by cruise ship, sailing aboard the Fury will be the highlight of your vacation.

Sailing Trinidad and Tobago

Sand Dollar Sailing Charter - Sand Dollar Sailing Charter is a locally owned, family run, yacht charter business that has been running in Trinidad and Tobago over the last 5 years. We encourage sailors to explore the beauty of the Caribbean Sea and to teach the skills of sailing to those on holiday interested in a little bit more.

Sailing Tortola (BVI)

Aristocat Charters - Aristocat is available for Private Charters, Beach Weddings and other Special Events. We currently offer two Day Sail Excursions. One heads South visiting Norman Island and the surrounding snorkel sites and the other heads West visiting Jost Van Dyke, stopping for swim and snorkel on route.

Barecat yacht charters - Barecat yacht charters in the BVI from Manuel Reef Marina in Sea Cows Bay, Tortola in the British Virgin Islands. Come to BareCat for a Caribbean sailing charter yacht vacation in Tortola and either charter a crewed or bareboat beautiful, spacious catamaran.

Kuralu - Visiting the British Virgin Islands? Come sailing on Kuralu, our 50� luxury cruising catamaran. With over 1,000 square feet of deck space, there's plenty of shade, an open bar all day and our famous buffet lunch, which is served onboard.

Tortola Bareboat Sailing Charters - Safety, cleanliness and boat maintenance have played a major role in our sailboat selection from several, Tortola based, bareboat charter companies.

White Squall II - When you are visiting the beautiful British Virgin Islands, a day spent sailing in the azure waters of the Caribbean aboard a beautiful classic Schooner, built in 1936, will be the most unforgettable day of your life.

Virgin Gorda (BVI)

Bitter End Yacht Club - Bitter End Yacht Club is the Caribbean's premiere luxury water sports resort, hosting family fun vacations, romantic getaways, and idyllic escapes for all.

Antigua and Barbuda Sailing

Aruba Sailing

Bahamas Sailing

Barbados Sailing

Cayman Islands Sailing

Curacao Sailing

St Croix Sailing

St John Sailing

St Lucia Sailing

St Maarten Sailing

St Thomas Sailing

Tortola Sailing

Tobago Sailing