Top Caribbean Sailing Tours

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.

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, with our spacious 48-ft yacht reserved exclusively for you and your group, never shared with others. Our mission is to show you the beauty of our island in a relaxed, crowd-free and welcoming atmosphere. Thanks to 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. Your safety, comfort and enjoyment are always our priority. Our well-equipped sailing yacht offers a smooth and relaxing experience on the crystal-clear waters of Curacao. As owners and experienced crew, we personally host every tour to ensure a laid-back, personalized and unforgettable private experience filled with beautiful sightseeing and relaxed sailing. Your Curaçao dream experience starts here!

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This trip is limited to only 12 guests. Start the morning a full open bar as we sail along the beautiful Northern Cays of the USVI. We check into the BVI Customs where you'll get to explore the town of Great Harbor with its sandy Main Street and maybe even meet Foxy himself while you get to enjoy some Fire Water Rum or grab a souvenir at the boutique. After Great Harbor we sail over to the beautiful White Bay, which is home to The Soggy Dollar Bar to spend the entire afternoon. This 9 hour trip will give the max time at White Bay. ** This is an International Excursion and a Valid Passport and USD85 cash customs fees per person is required ** This is a share trip with other guests. This is NOT a private tour. The tour operator is not be responsible for closures of other businesses and it is the guest's responsibility to research closures prior to booking.

Step aboard a catamaran with friends and family for a private cruise up the coast of the Dominican Republic. You'll be received by a captain and crew dedicated to your enjoyment; you can ask questions and learn about the marine environment through their commentary. Stop to swim, snorkel, and use the flotation devices between enjoying snacks and drinks from the open bar.

Our tours are unique in that we carry limited numbers (maximum 10 guests) and the experience is personalised, in an uncrowded atmosphere. We also provide all the snorkel and safety equipment for our guests and avoid the crowds as much as possible whilst snorkelling.

Get close-up views of tropical fish, coral, and other marine life on this fun, half-day glass-bottomed boat tour. Relax on board as you enjoy the views and take advantage of the provided snacks and drinks. If you don't mind getting wet, don some snorkeling gear and swim at a beautiful natural swimming pool. An ideal trip for the whole family.

Toast your trip to the Dominican Republic on board a party boat. This catamaran cruise takes you and a crowd of revelers along Punta Cana's gorgeous coastline while the alcohol is free-flowing and the music is pumping. You can enjoy the scenery on deck and jump off board to snorkel around a pristine coral reef.

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) it’s a virgin island with beautiful beaches and speechless coastlines full of palm trees. While on the island you can relax on a chair lounge, hang out by our all inclusive beach bar, play beach volleyball. Around mid day we open our beach buffet for a typical Dominican lunch that includes: chicken, pork, rice, vegetables, beans, salad and fruit, or walk the coastline.

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.

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!

Avoid the cramped feeling of group boat tours and explore the US Virgin Islands on your own terms with a private sailboat charter just for your group. Hop aboard a luxury catamaran and head out to sea, stopping along the way to snorkel at special spots known for their great abundance of wildlife or at pristine beaches that few travelers visit.

Experience the waters of Punta Cana through watersports that anyone can enjoy—snorkeling and a banana boat ride—on this 2.5-hour afternoon tour. Head out on a speedboat with a group of fellow adventurers, then hop on a banana boat to be pulled behind the speedboat for a thrilling ride. Slip on some snorkel gear to explore the underwater world; guides will be on hand to provide instruction and information about the resident marine life.

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.

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, offering everything from relaxed family cruises to romantic escapes in a peaceful, crowd-free atmosphere. With a strong eye for detail and genuine passion for hospitality, we’re proud to receive outstanding reviews and Travelers’ Choice recognition from Tripadvisor and Viator guests. Your comfort, safety and enjoyment are always our priority. Our spacious and well-equipped 48-ft sailing yacht ensures a smooth and relaxing experience on the water. We believe in a personal and laid-back approach, making every private boat tour feel intimate and tailored to you. As owners and experienced crew, we’re passionate about sailing, the sea and sharing the beauty of Curacao. Together, we create maximum private experiences with breathtaking scenery, relaxed sailing and a comfortable yacht exclusively reserved for you and your guests. Your Curacao dream experience starts here!

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.

The experience balances scenic cruising, relaxing time at anchor and a peaceful sail back with the sails raised when weather conditions allow. As owners and crew, we personally welcome you aboard to provide a comfortable, private and memorable experience from beginning to end. With Maxie Sailing, you’ll discover the beauty of Curacao in comfort, privacy and relaxed luxury aboard our spacious 48-ft sailing yacht. We welcome exclusively your group on board and personally host every charter ourselves. Our dedication to safety, comfort and personalized service has earned us outstanding reviews and the Travelers’ Choice Award from Tripadvisor and Viator. This private tour is perfect for cruise travelers, couples, families and special occasions, this experience offers a peaceful, crowd-free way to create unforgettable memories on the crystal-clear waters of tropical Curacao. Your Curacao dream experience starts here.

Planning a day of snorkeling around St. Thomas can mean arranging a boat, equipment, food, and deciding where to explore. Leave the details to the crew on this sailing trip featuring multiple opportunities to snorkel and enjoy beach time. Snorkeling gear is provided, while lunch from the floating Pizza Pi boat, additional refreshments, and an open bar make for an easygoing day on the water.

Avoid the crowds - All tours are limited capacity for more social space, outstanding personalized service, and to help promote sustainable tourism. Enjoy the best of both worlds, sailing and snorkeling with turtles. St. Thomas's most sought-after two stop catamaran experience puts you next to graceful sea turtles in the warm Caribbean waters. This thrilling luxury sailing catamaran ride along the picturesque southern coast of St. Thomas will take you to Turtle Cove and Buck Island National Wildlife Refuge where your professional snorkel guide will provide you with all the necessary instruction to use your snorkel gear, and take you along the surface on an unforgettable, fun, and informative marine life adventure. You will swim amongst numerous species of colorful fish, beautiful coral reefs, and endangered green sea turtles. Upon your return from snorkeling, you will enjoy fresh snacks and drinks from our premium open bar. Then we are off on a relaxing sail back to St. Thomas.

Cruise the waters of the Turks and Caicos Islands—without having to battle for room on a crowded boat—on this private sailing charter. Relax onboard with plenty of room to stretch out, with time to snorkel, swim among marine life, and explore secluded beaches. Along the way, refuel with a freshly cooked barbecue, washed down with drinks from the open bar.

Experience the magic of Jamaica’s Luminous Lagoon on this breathtaking night-time tour. Cruise across glowing waters illuminated by bioluminescent microorganisms, and take a dip in the surreal, glowing waters. Enjoy drinks, music, and local "liming" as you soak in the natural beauty of this unique Caribbean wonder.

Are you and your group seeking a private catamaran experience, tailored to your preferences, without sharing it with other guests? Look no further – our private charter option is your ideal choice! Customization Options Include: 0-2 snorkeling spots Stingray City Starfish Point Step aboard the Buccaneer, a stunning vessel that will be your companion on a captivating 4-hour voyage. Your journey commences with an exploration of the mesmerizing Coral Gardens, one of the Cayman Islands' natural wonders. Here, you'll have the opportunity to snorkel and immerse yourself in the underwater paradise, where vibrant tropical fish and beautiful wild marine life await your discovery. The world-renowned Stingray City, where you can partake in the unique tradition of receiving a kiss from these gentle giants for seven years of good luck. Experience the magic of the Cayman Islands with us, where every moment promises wonder and adventure.

Skip your usual sightseeing tours for a unique way to explore Punta Cana's coastline—parasailing. Instead of enjoying the scenery from land, hop aboard a speedboat before rising high above the water for an aerial view—something most travelers never get to experience.

We are the only excursion that allows you to drive the boat during this private excursion. We are the only boat that sails in the dark, at night, wait till you see that sky and moon.!!

- Private 1.5-hour sunset cruise aboard Kona, a sleek catamaran - Scenic sail along Bermuda’s coastline with golden hour views - Ideal for couples, small groups, and special occasions - Enjoy the onboard bar or bring your own beverages and snacks - Licensed local captain ensures a smooth, safe, and relaxed experience