Top Caribbean Sailing Tours

I invite you to come and share my passion for sailing and navigation in one of the most beautiful bays in the world! I am a State Sailing instructor, I grew up on a boat around Guadeloupe and its islands, and I invite you today to come and discover the playground of my childhood!

Set sail for a one-of-a-kind adventure on the Caribbean Sea! Join us aboard our vibrant, high-energy Punta Cana party boat for an unforgettable day of sun, fun, and celebration. Whether you're marking a special occasion or just living life to the fullest, our crew is ready to make your experience truly legendary. LUXURY EXPERIENCE! Live your best VIP moment in Punta Cana! Celebrate your birthday, bachelorette, spring brake, anniversary, or special occasion aboard a private luxury boat with a 5-star captain & crew Exclusive Onboard & Water Activities: ️ * Cruise to a Natural Pool off the coast of Bávaro Beach – where the party truly begins! * Snorkeling Adventure at vibrant coral reefs * Scenic Cruise by Dolphin Island – Spot dolphins from the boat * Beach Stop – Relax and soak up the tropical vibes

What makes this tour truly unique is the perfect balance of adventure and relaxation in one unforgettable experience. You’ll explore the stunning waters of Carlisle Bay, home to some of the most accessible and fascinating shipwrecks in the Caribbean, giving you the rare opportunity to snorkel among history and vibrant marine life all in one place. Unlike typical snorkel trips, this experience goes beyond just the water. With a relaxed atmosphere onboard, complimentary drinks including rum punch and local beers, and our signature floating bed for ultimate comfort, you can seamlessly switch between exploring and unwinding. It’s a more personal, laid-back cruise designed to let you enjoy the ocean at your own pace—whether you’re snorkeling over shipwrecks, soaking up the sun, or simply floating your worries away.

What makes our Saona Island tour different is the perfect balance between relaxation, adventure, and authentic Dominican charm. Unlike standard excursions, we combine speedboat and catamaran so you experience both the thrill of a fast ride and the fun atmosphere of music and entertainment on the way back. Our tour includes a delicious Dominican buffet right on the beach, plenty of free time to enjoy the island at your own pace, and a stop at the famous Natural Pool, one of the Caribbean’s most iconic spots. With personalized attention, comfort, and a lively atmosphere, we make sure your day in Saona is not just a trip, but an unforgettable experience worth sharing.

Experience Bonaire’s Friday night from the water aboard our 80-foot Brazilian wooden schooner. Enjoy great music, drinks, a tasty bite, sunset views and a relaxed social atmosphere while cruising along Bonaire’s coastline. A unique way to meet people, unwind and start your weekend on the water.

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this public sail is a perfect outing for family and friends. All ticket proceeds contribute to the World Ocean School's educational programs, ensuring a meaningful experience on the water. Enjoy an enriching day while supporting maritime and experiential education.

In an intimate setting (max 7 people), come and discover the Saintes archipelago by sail! I'll take you to Terre de Bas to observe the pelicans and jump into the water in search of sea turtles! Together, let's hoist the sails, take the helm of the catamaran, and enjoy the silence of sailing.... The Baie des Saintes is classified by UNESCO as one of the most beautiful in the world, and follow the famous Pain de Sucre to the rhythm of the trade winds is simply spectacular!

Saona Relax is distinguished by its gourmet seafood paella lunch and exclusive access to Tao Beach Club, an experience superior to the typical island excursion with buffet lunch. Added to a snorkeling stop, the iconic Natural Pool and cocktails included, you will enjoy a premium Caribbean day, relaxed and unlike any other.

Visit Cayo Levantado (Bacardi Island) and El Limón Falls. Enjoy a true experience of the Eastern Coastal Plain of the Dominican Republic, traveling from different hotel zones in modern and comfortable buses.

Take in views of Basse-Terre Island’s dense mangroves and craggy reefs from a perspective that most travelers never get to experience on this small-group full-day sailing tour. Hop aboard the boat at Baie-Mahault and get ready for a day of relaxation, snorkeling, and wildlife-spotting as you explore coral reefs and protected waters teeming with marine life.

Join us aboard Be Happy for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private sailing experience with your group, discovering the island’s stunning coastline and crystal-clear waters in complete comfort and privacy. Our attentive crew will pamper you with refreshing drinks, delicious snacks, and warm hospitality while sharing fascinating stories and fun facts about the island along the way. To make your experience even more enjoyable, we provide snorkeling gear, swimming noodles, a paddleboard, and a floating mat, or should we call it a floating bar! Choose your preferred half-day charter: Morning Charter: 9:00 AM – 1:00 PM Afternoon Charter: 2:00 PM – 6:00 PM Come aboard Be Happy and create unforgettable memories on the water!

Visit St. John for the day on this easy tour from St. Thomas. Meet at The Ritz-Carlton beach to board the luxury Lady Lynsey. Enjoy lite breakfast bites before arriving at Cruz Bay, where you can stroll the beach, shop, and have lunch on your own. Afterwards, snorkel in Virgin Islands National Park, then relax with an open bar on the return sail to St. Thomas.

First, we sail to the paradise Island of Icacos aboard the modern, 51 ft. sailing catamaran,  SPREAD EAGLE II!  The brisk 40 to 50-minute sail to the protected anchorage off of this uninhabited Spanish Virgin Island is beautiful. Sparkling beaches and crystal clear snorkeling waters await. We think you deserve the best, don’t you? Over 65% of our guests are repeats or referrals. The reefs are teeming with parrot fish, foureye butterfly fish, sergeant majors, and wrasse. The variety is too long to list, so you should just come see them all for yourself. Ask one of the crew to see the Fish, Coral, and Shell Identifying Charts on board. SPREAD EAGLE II even provides lunch for the fish. With a little patience, you can get the fish to eat bread right out of your hand.

Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating areas, bar, and restroom for the enjoyment of passengers. Scenic Coastal Routes: Allowing passengers to enjoy the picturesque coastal area, the perfect snorkel-populated stop. Knowledgeable Guides: Experiences and knowledgeable guides who are passionate about the marine environment. Snorkeling and Marine Activities: The opportunity for snorkeling and engaging in various marine activities. Explore vibrant coral reefs, with tropical fish, and sea turtles (protected). Exceptional Cuisine: Delicious local lunch on board or on the beach in Nevis, open bar with refreshing beverages. Commitment to Sustainability: Committed to responsible tourism and sustainable practices. Prioritizing the protection and conservation of the marine environment, minimizing the footprint. Providing exceptional catamaran tours combining adventure, knowledge, comfort, and sustainability.

On this 4-hour sail we have combined the excitement of Sailing on a great trimaran, Swimming/Snorkeling in turquoise waters of a calm bay on the west coast of St.Maarten and to top it all off the sail back to home port is during a Caribbean Sunset. On this sail there is no music other than the wind in the sails, water against the hull. On each of our experiences 16 guests is the maximum capacity.

Sailing has sensation. Come live an unforgettable experience on a sailboat. A timeless adventure aboard our sailboat. Come hoist the sails on the Caribbean Sea and guide the boat according to the wind. Come hold the helm of the ship with the assistance of the captain! Enjoy a monohull type ship and enjoy gliding on the seas.. Experience adventure aboard a sailboat from Fort Louis a Marigot Saint Martin Marina.

Enjoy a relaxing day out on the water in Granada without having to share a boat with crowds of strangers. This private catamaran cruise is just for you and your private party. Sail from Halifax Harbour along the southern coast of Granada and admire the views. Bring your own picnic or arrange for catering to be provided on board. Kayaks, stand-up paddle boards, and snorkeling gear are provided to use.

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the luxuries for a comfortable, safe, and sustainable cruising experience. This all-inclusive sailing package is a boutique experience complete with your own captain and crew catering to your every need. It's pure luxury every step of the way. From the moment you slip off your sandals and step aboard Freedom’s sprawling teak deck, you’ll be warmly welcomed with a cool scented towel and nibble a decadent handmade chocolate as you head over to one of the luxurious lounge areas to begin a leisurely morning sail. With a sparkling mimosa in hand, you set the vibe while your experienced captain and crew take care of the rest.

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from your hotel to Negril. Once you arrive in Negril, you will be escorted to the Catamaran for you to start your excursion. You will get to experience the famous 7 mile Beach, party boat vibes and also the world's famous Ricks Cafe at the end of your activity. You will not regret booking this excursion with you. Make your vacation the best one yet.

Set sail along the Caribbean coast during a 6-hour boat tour around Martinique. With maximum eight passengers on board, your day away from shore is sure to be relaxing. Visit a secluded bay where you can swim and snorkel with the local sea life. Lunch is prepared using local ingredients and can be made to accommodate dietary restrictions. Be sure to try an authentic Creole cocktail made with local rum.

Be as active or as relaxed as you like on this full-day cruise around St. Maarten aboard the “Hakuna Matata” catamaran. Families, couples, friends, and solo travelers are all welcome aboard. Stop at many beaches along the way—including places you wouldn’t reach any other way—and enjoy swimming, snorkeling, or just relaxing on the beach. Food and drinks are provided on board so you don’t need to bring your own.

Discover BVI’s legendary Anne Bonny—a classic 60ft sailing yacht with pirate soul! Snorkel the iconic Caves & party at The Willy T floating bar. All-inclusive: gear, open bar (mimosas, rum punch), fresh lunch. Expert crew tailors every Thursday’s shared adventure to weather & guest vibes. Intimate groups, flexible fun—perfect for couples, friend groups & solos (12+). Book now & live the BVI dream! ⛵

Enjoy a relaxing and fun day on the water on this half-day cruise along the Punta Cana coast. Snorkel along a coral reef filled with tropical fish and visit a unique natural pool. When the bar opens, it’s time for an island party with music, dancing, entertainment, and swim-up service. The festive atmosphere continues on the return trip to the marina.

Tiami Catamaran Cruises offers more than just a cruise—it delivers an authentic Barbadian experience. Renowned for its warm hospitality, experienced crew, and spacious catamarans, Tiami blends relaxation, adventure, and exceptional service on every sailing. Guests can indulge in a delicious Bajan buffet lunch, snorkel among colourful tropical fish and sea turtles in crystal-clear waters, and unwind on spacious decks with a fully stocked open bar available throughout the day. Whether you're seeking adventure or simply looking to relax, Tiami provides the perfect escape. Ideal for families, couples, friends, and groups, Tiami's commitment to quality, safety, and genuine Bajan hospitality has made it one of Barbados' most trusted and iconic catamaran cruise experiences.