Top Caribbean Sailing Tours

Enjoy a private romantic sunset cruise and 3 course dinner for two or for a for a group of up to 6 friends. We offer a more intimate experience than many other sailing companies in Aruba. This allows you to relax and enjoy the company of your loved ones without feeling crowded. Enjoy a delicious dinner and open bar. So you can sit back, relax, and enjoy the beautiful scenery without having to worry about a thing. Great customer service! The crew is friendly and professional, and they'll go out of their way to make sure you have a memorable experience. Book now for a captivating evening of love and luxury on the waters of Aruba.

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.!!

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

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy all the beauty our island has to offer in the privacy of your own group. Our attentive crew will pamper you with our on-board offer and captivate you with stories and fun facts along the way. All our day charters come with our selection of drinks and snacks, and plenty of activities for you to enjoy such as snorkeling gear, swimming noodles, paddle board and a floating mat (or should I say floating bar)!

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

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

- 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

Escape to the tranquil and world-renowned island of Anguilla while you sail 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.

Escape the crowds on land and have some sun-soaked fun in the Caribbean Sea on a private party boat tour in Punta Cana. Tailor your itinerary to include as much swimming, snorkeling, and sunbathing time as you like, and enjoy an open bar with top-quality drinks, plus snacks and soft drinks to keep you hydrated.

Jamaica is an island paradise and one of the best ways to immerse yourself in its serenity is doing so from the topside of a boat. Live it up in a luxurious way when you book this private all-inclusive catamaran experience in Montego Bay. This cruise treats you and your group to hours of relaxation with rum punch and snacks. Sunbathe, swim, or dance to music as you sail around Doctor’s Cave Beach.

Join us on Mojito one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy all the beauty our island has to offer in the privacy of your own group. Our attentive crew will pamper you with our on-board offer and captivate you with stories and fun facts along the way. All our day charters come with our selection of drinks and snacks, and plenty of activities for you to enjoy such as snorkeling gear, swimming noodles, paddle board and a floating mat (or should I say floating bar)!

Boats and water sports are a must do while in Turks and Caicos, and this Grace Bay Hobie Cat Sailing Lesson shows you the basics of sailing a small sailing catamaran so you can go out again on your own. A captain goes over the fundamentals of sailing a Hobie Cat in an interactive environment where you can ask all the questions you need to to nail down your skills.

Discover a different side of Punta Cana with a Scuba Doo underwater scooter experience that lets you explore beneath the Caribbean Sea without traditional scuba diving. Ride your own easy-to-use underwater scooter while breathing comfortably inside a clear helmet system, giving you a wide view of colorful tropical fish and marine life around the reef. What makes this experience special is how simple and accessible it feels: no scuba certification is required, and professional staff stay nearby to assist throughout the activity. The adventure also includes a scenic boat ride, time to enjoy the Caribbean surroundings, and a fun combination of underwater exploration and ocean sightseeing. Perfect for couples, families, friends, and first-time underwater explorers, Scuba Doo offers a memorable way to experience Punta Cana’s marine world from a completely different perspective.

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy all the beauty our island has to offer in the privacy of your own group. Our attentive crew will pamper you with our on-board offer and captivate you with stories and fun facts along the way. All our day charters come with our selection of drinks and snacks, and plenty of activities for you to enjoy such as snorkeling gear, swimming noodles, paddle board and a floating mat (or should I say floating bar)!

Sail just offshore of the coast of Grenada. Enjoy snacks and drinks while taking in the remarkable view of the crimson sun falling into the Caribbean Sea. Is there anything more beautiful than enjoying a sunset out at the sea with a glass of champagne? Pure romantic. A breathtaking trip for young and old, for lovers and great for families!

Enjoy a fun-filled half-day on a catamaran booze cruise. After pickup from your hotel in the afternoon, cruise along the coast aboard a double-decker catamaran with slide, and enjoy music, snacks, and drinks from an open bar. Time at the natural pool and a 30-minute snorkeling stop is included, with all equipment provided.

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! What ever 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.

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the vibrant underwater world, and enjoy the crystal-clear waters. In addition, there’s the added pleasure of an open bar, fresh fruit, chips, and savory Jamaican patties. Our signature drink the “Tipsy Gypsy” is a must try! For your listening pleasure, we also have a Bluetooth sound system, allowing you to sync your favorite playlist. We look forward to providing an unforgettable experience immersed in the natural beauty of Jamaica!

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you to explore around our stunning islands waters at your own pace. Indulge in a selection of homemade meals, including fresh sandwiches, grilled dishes, and locally foraged ingredients, all crafted with care by our crew. With over 20+ years of experience sailing, Captain Robert will lead you on an unforgettable adventure, sharing tales of the islands, the sea, and his global voyages—each one more fascinating than the last. Choose how you spend your day: relax with a drink on deck, snorkel in crystal-clear waters, hike to hidden beaches. Should the weather not cooperate, we’ll happily reschedule your trip for another day. For any special requests or questions, feel free to contact us directly. Set sail with us for a day of Caribbean relaxation and adventure—tailored just for you!

Enjoy a private sunset cruise on a 55-foot daysail yacht with space for up to 12 guests. Meet at Sapphire Beach Resort Marina to board the yacht, then relax as your captain sails to Great St. James and anchors in Christmas Cove. Watch the sunset while savoring hors d’oeuvres and drinks from the open bar.

We enjoy a catamaran tour across crystal clear waters to Catalina Island, the best-known area for snorkeling in the Dominican Republic.Your day begins with a pick up at your hotel main lobby or specified meeting point. Then we´ll continue to Catalina Island to enjoy a refreshing bath, and some drinks, while whoever can perform 2 types of Snorkel with an instructor and after we will eat a delicious lunch buffet at the beach and we´ll take some clases of Salsa and Bachata, while we also take some delicious drinks. Once tired of being lazy on the beach,grab some snorkeling equipment and admire Catalina’s underwater world. The ocean, so incredibly clear, and the beach white sand, wait for you. Relax on a sunbed or snorkeling all included for you. You will enjoy where you will see the tradition of our music and dances. In the afternoon we´ll return to Catamaran back to the Port of La Romana to start back to hotels.

Explore the Virgin Islands in style with a full-day private sailing tour from Sapphire Beach. You and your group of up to six passengers will have the boat to yourself. Create a custom itinerary with your captain and crew, whether you want to sail all day, visit secluded beaches, or drop anchor and swim, snorkel, or play in the water. Enjoy lunch onboard and refresh with a fresh water shower rinse.

ScubaDoo Punta Cana is a diving and snorkeling adventure that takes you to some of the most beautiful and unspoiled areas in the Caribbean Sea on board of one of our Scuba Motorcycle or known as scooter and enjoy the Scuba doo diving as a true diver. The ScubaDoo experience is unique in that it allows you to explore the underwater world using an underwater scooter During your ScubaDoo adventure, you will have the opportunity to see a variety of marine life, including colorful fish, coral, and even shipwrecks. The guides are knowledgeable and will take you to the best spots for maximum visibility and marine life sightings.  It doesn’t matter if the client doesn’t have prior knowledge of diving or Scooter, since the interface of our Scuba doo or Scuba bike is designed to be made by children from 10 years to adults over 70 years. Customers can wear glasses or prescription glasses as this doesn’t prevent them from taking the tour, there is no weight or height l

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs and shipwrecks, paddle around a secluded island, or jump from cliffs into turquoise waters, we’ll shape the day around you. With over 20 years of experience, we’ve been perfecting the art of bespoke charters—knowing when and where to go, how to avoid the crowds, and how to make every moment seamless. From hand-picked anchorages to onboard catering served with care, every detail is handled so you can relax. You won’t find rigid itineraries or crowded decks here—just space, comfort, and the freedom to explore Bermuda at your own pace, with a knowledgeable local crew by your side. Please note that you may bring up to 15 passengers in total, including yourself. All of our charters are private, so it will be just you and your group on board.