Top Caribbean Sailing Tours - page 9

Where golden skies meet calm seas — sunset cruising along the south side of St. Maarten on our luxury sailing catamaran, Be Happy.

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.

Embark on a sleek powerboat for an unforgettable 3.5-hour adventure that combines snorkeling, delicious bites, and a stunning sunset experience. Begin with a vibrant snorkel stop at a pristine reef, where all snorkel gear and instruction is provided and our crew is ready to help you explore the underwater world. After snorkeling, relax as you cruise into golden hour and enjoy fresh, hot pizza—cheese or pepperoni—delivered from the famous Pizza Pi boat, paired with drinks from our open bar. This trip is perfect for anyone seeking relaxation, great food, and breathtaking views of the Virgin Islands. 3.5-hour trip featuring snorkeling and a scenic sunset cruise Snorkel at a hand-picked site known for clear waters and abundant marine life Enjoy fresh cheese or pepperoni pizza from the iconic Pizza Pi boat

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical Sailing will provide you with the memory of a lifetime! This boat charter is private! You are special enough to deserve all of our attention! We sail on your schedule! When you charter with us, we will work with you to provide unsurpassed flexibility and excellent service.

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.

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! ⛵

Create unforgettable memories with this exclusive private sailing experience in Curaçao. Our elegant 48-ft sailing yacht Galaxie is reserved entirely for your group, allowing you to enjoy the island’s stunning beauty in a relaxed, intimate and crowd-free atmosphere. With exceptional attention to detail and a strong focus on personalized service, we are proud to receive outstanding reviews and the Travelers’ Choice Award from Tripadvisor and Viator guests. Your spacious yacht is fully equipped for a smooth and comfortable experience on the water, with your safety, comfort and enjoyment always our highest priority. As owners and experienced crew, we personally host every tour to ensure a laid-back and memorable experience from beginning to end. Your Curaçao sailing and snorkeling adventure starts here!

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.

Enjoy smooth sunset sailing on one of our catamarans along the coast of Bonaire. Let us get you spoiled with luxury snacks, drinks and chill background music onboard while watching the sunset.

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!

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!

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.

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.

What makes our experience unique is the perfect mix of Caribbean rhythm, crystal-clear waters, and true Dominican hospitality. Our goal is always your happiness — that’s why our catamarans are safe, spacious, and full of fun energy. This experience is for travelers who love great music, friendly hosts, tropical drinks, and unforgettable vibes under the Punta Cana sun. Whether you’re celebrating a birthday, wedding, bachelor party, or simply want to dance and relax, our crew makes every moment special. You can book it privately for your group or share the adventure with other guests — either way, it’s always a great party at sea!

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.

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 en route to 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.

This is a small group tour with only a maximum of 12 guests. We depart from American Yacht Harbor in Red Hook and sail to world famous Pizza Pi, where you will have a chance to enjoy a quick snorkel and pizza from Pizza Pi. We will depart Christmas Cove and you will have the best seats in the Virgin Islandst. There is not a better place to watch Mother Nature show off her beauty than the bow of a catamaran sailing through the Pillsbury Sound with a cold drink in your hand. Experience the most relaxing time of the day and lets celebrate the end of a lovely day in paradise together!!

1. An exceptional natural setting: crystal clear waters and preserved beaches offer an idyllic setting. 2. Marine richness : snorkeling allows you to explore a rich and colorful marine biodiversity. 3. Friendly environment : catamaran excursions promote interaction and sharing between participants. 4. Gastronomic meals : tasting of local specialties and fresh products on board. 5. Diverse experiences : varied activities (paddling, relaxation on the beach) for all tastes. These elements together make Tintamarre a unique and memorable destination

J/24 Interactive Day Sail in Barbados. Learn, Sail & Play! Trade your beach towel for a mainsheet and experience real sailing aboard a sporty J/24 keelboat!. This hands-on day sail is perfect for beginners and curious adventurers who want more than just a boat ride. Learn the basics from certified instructors, then take the helm, trim the sails, and feel the wind power your journey along Barbados’ stunning coast. With only 4 guests onboard, everyone gets plenty of time at the wheel. The J/24 is fast, fun, and the most popular racing boat on the island—come sail like the locals do! Enjoy warm trade winds, turquoise waters, and the pure joy of engine-free cruising. No crowds, no experience required—just bring your sense of adventure. This is sailing stripped down to its joyful core. Book your J/24 Interactive Day Sail today, and leave the shore behind with a salty grin and a new skill to brag about!

Enjoy comfort of slow sailing catamaran and scenic views of Sint Maarten in sunsetting light. Admire a magnificent Sun stepping down below horizon taking the light away for the ocean just to bring it back the next day on opposite side of the globe

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.

Our Catamaran Party Boat Tour is a MUST when it comes to Punta Cana experiences. This booze cruise takes you along the Coast of Bavaro to the most popular Natural Pool in the Dominican Republic - and that's only the beginning! You can enjoy delicious snacks, all-inclusive national drinks, snorkeling, music, and more while sailing the Atlantic Coast on this unique party boat. With plenty of space for everyone to dance and party, it's perfect for a day out on the water with friends.

Are you looking for a wedding proposal, anniversary or an unforgettable date, you are in the right place! The boat has plenty of space for a romantic couple. You will experience a private moment with your date or fiancé on a luxury yacht while cruising along the beautiful coast of Bonaire enjoying a glass of champagne.

Celebrate love with an unforgettable private romantic sailing experience in beautiful Curacao. Surprise your partner with a breathtaking sunset yacht escape designed for couples seeking intimacy, relaxation and unforgettable memories - whether you’re celebrating a honeymoon, anniversary, special occasion, or even planning the perfect proposal. Enjoy the comfort and privacy of our elegant sailing yacht, reserved exclusively for the two of you and hosted personally by us as your captain and crew. Together, we’ll show you the stunning beauty of Curaçao in a peaceful and crowd-free atmosphere. With our attention to detail and dedication to exceptional service, we are proud to receive outstanding reviews and the Travelers’ Choice Award from Tripadvisor and Viator guests. Relax together on a private boat with scenic cruising, beautiful sunset views, delicious food and drinks and a truly intimate experience on the blue waters of Curacao. Your unforgettable Curacao love story starts here.