Sailing in St. Thomas Virgin Islands is the epitome of a relaxing vacation activity. Cruise away from the shoreline, catch the trade winds in your sails, take in the magnificent scenery, and pull into a quiet bay to swim, snorkel and have lunch. You will find a list below of some of the finest sailing charters in St. Thomas. Sailing conditions in the USVI are spectacular. What’s more, St. Thomas’ captains are top notch. Their experience might include growing up in sailing families, living on a boat, sailing around the world, and competing in regattas. Ask your captain for a tale or two about their sea-faring life. St. Thomas charters include full day sailing trips, half day excursions and romantic sunset sails. If you are a fan of fleet racing and sailing competition see the section on St. Thomas regattas at the end of this page.
Featured Sailing Charters
Grateful Day Charters
At Grateful Day Charters we provide you and your family with an all-inclusive adventure. We offer Sail and Snorkel Cruises, Romantic Sunset Sails, Family Pirate Adventures, All Inclusive Packages and can customize a charter based on your requests. We take the time to help you create the very best personalized experience; making sure you get the most out of your charter. Guaranteed to engage you with the rich natural environment, provide unique experiences, and memories that you and yours will cherish for a lifetime. Charters include world class sailing, delectable dishes, well stocked bar, swimming and snorkeling gear. Contact us today!
Catania Yacht Charters
Come Sailing with Catania Yacht Charters: excursions in the USVI and BVI, specializing in small groups of up to 6 guests. Catania is a traditional 80 year old sloop with a legacy of spending over 30 years circumnavigating the globe. Be pampered on an unforgettable excursion of a lifetime. Captain Ocean will enthrall you with the history of the Virgin Islands and stories of his around the world voyage. Discover pristine white sand beaches and enchanting hidden coves. Experience an underwater world full of spectacular marine life. Enjoy refreshments from our open bar. Full day, half day, and sunset sails available.
Sailing the Cosmos Charters
“Cosmos Mariner” is a classic Robert Perry designed Baba 40′ Pilot House. With an overall length of 48′ she provides the perfect blend of comfort, stability, and style. Impeccably maintained she ensures a first-class luxury experience for up to 6 guest. Whether you are seated in the shaded cockpit or soaking up the sun on the large padded foredeck you’ll find all the amenities necessary to complete the perfect day on the water. Contact us today for more information about our semi-private or private half day, full day and sunset sails.
Sail with Liberty & Justice Charters
Sail with Liberty and Justice welcomes you aboard for a memorable full day sail, half day sail, or sunset sail for up to 6 guests. We also offer private sails and excursions. Sail among the tropical islands and cays of St. Thomas and St. John National Park on our beautiful Bruce Roberts Offshore 44′ ketch or our Voyage 430 luxury sailing catamaran. Captain Ryan treats guests to a fun-filled day with amenities that include a delicious lunch, refreshing drinks, shaded cockpit, spacious decks, great snorkel and flotation gear, convenient swim platform, and terrific rates. TripAdvisor reviewers rank Sail with Liberty “Excellent.” More info at sailwithliberty.com.
Have you always wanted to sail through the beautiful Caribbean waters, snorkel pristine coral reef habitats, or learn more about the history and legends of the U.S. Virgin Islands? Join us at Rumbaba Charters for a private sailboat charter (Up to 12 people). With our gourmet food and open bar, you can float the waters with a refreshing cocktail and get a taste of local food cooked while you swim. You can sit back, relax, and let our professional crew handle everything! You can customize your own private day sail or sunset sail. We offer unique activities including snorkeling and swimming with sea turtles! Join us for an unforgettable vacation adventure during your time in St. Thomas.
Looking for an unforgettable day on your Caribbean vacation? Spend the day on a luxury sailing yacht with Max Charters! With Captain Hunter you will sail in the National Park on St. John to the protected bays that are perfect for turtles, and who doesn’t like turtles, and fish. Max Charters sails with a maximum of six guests, if you would like the boat all to yourselves just ask for a private trip. Charters include: sailing, snorkeling, an unforgettable Mediterranean style lunch and open bar. What could be better!
Stormy Pirates Boat Charters
Whether you are looking for a Private Full Day or 1/2 Day Sailing Adventure or you are a Solo Traveler, Small Family or a Couple looking to join a Scheduled Tour at Per person Pricing, Stormy Pirates Boat Charters has you covered!! Our 41′ Fountaine Pajot sailing catamaran is the perfect way to explore the beautiful Virgin Islands in style and comfort. On your boat day our friendly crews will cater to your every need. We offer a well-stocked Open Boat Bar, Light Snacks, use of Snorkel Equipment, a SUP and Kayak. We only take a maximum of 10 people on every trip, so you will receive a very personalized experience.
Spend the best day of your vacation aboard Independence, a big, comfortable ketch, cruising the bays of St. John and the small islands in Pilsbury Sound. She is equipped with awnings for shade, mats for sunbathing, top notch snorkel gear and all US Coast Guard required safety equipment. Captain Pat Stoeken has been delighting guests with sea stories, delicious meals, beverages, great sailing and snorkeling for over 20 years. A limit of 6 guests and a crew of 2 make for a personalized experience. Half or full day. Let us know what we can do to make a special day for you.
Yacht Rock Charters
Join Cpt. Jarad Astin and crew aboard the vessel “Catherine” for a day of sailing you will not soon forget! Sailing and snorkeling are at the top of your vacation must-do list, which is no surprise in one of the sailing capitals of the world. Combine perfect weather with amazing snorkeling, top-quality food and beverage, and you’ll be pampered by our gracious crew for unforgettable memories. Our Captain and crew have sailed extensively throughout the waters of the Virgin Islands and beyond, with over 40,000 nautical miles on the vessel Catherine alone. We look forward to taking you sailing. Contact us today.
Seas the Day Charters and Tours
Seas the Day Charters offers luxury boat tours and excursions throughout the Virgin Islands. Enjoy a full or half day excursion to the white sandy beaches of our islands or an exciting day snorkeling the coral reefs with tropical fish, turtle and sting ray. We are a full-service charter company based in St. Thomas USVI that works tirelessly to ensure you and your guests enjoy your time while in the Virgin Islands. From private day sails, week long vacations to fast and fun trips to the British Virgin Islands, we will ensure you have fun and stay safe doing it!
St. Thomas Yacht Club and Regattas
The St. Thomas Yacht Club (STYC), in the US Virgin Islands, hosts multiple sailing regattas throughout the year. If you are an avid sailor and planning a vacation to St. Thomas, then consider picking a time when you can get in on the sailing action for which St. Thomas island is renowned. Contact the STYC for information on races. St. Thomas sailing regattas include Columbus Day Regatta, MLK Regatta, Round the Rocks Race, and the most well known the St. Thomas International Regatta (STIR). STIR was first sailed in 1974 and has continued with an exceptional program of serious world class yacht racing that has earned it the status of the ‘Crown Jewel of Caribbean Yacht Racing’. STIR attracts both the latest yacht designs and hottest one-design classes as well as the greatest skippers and crews from across the globe. STYC has produced champion sailors through its Junior Sailing Programs. It hosts a regatta for young sailors, the International Optimist Regatta.