St. Thomas: Sailing Charters & Excursions

Enjoying the magnificent waters around St. Thomas will be the highlight of your vacation. Sail into small quiet coves, snorkel at beautiful reefs and just bask in the delightfully warm sun and tropical breezes. Or take a sunset sail and enjoy the tranquil beauty and romance of Caribbean evenings. Many sailing charter boats are 6-packs, holding a maximum of 6 passengers. There are larger boats that can accommodate groups. Charters are available in half day trips, full day, sunset sails, dinner cruises and also overnight trips or Term Charters. While in the Virgin Islands you can also Learn to Sail. Prices on day trips average around $85 to $125 a person, depending on charter and length of trip. Amenities vary but might include open bar, lunch, snorkel gear, floats and other water toys. Visit the featured charters below!

Featured Sailing Charters

  • Independence

    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.

  • Daysail High Pockets

    A Cut Above! Join Captain Kathleen, a Registered Nurse and gourmet cook, for an outstanding day aboard the classic elegant yacht, High Pockets. Featuring spectacular sightseeing under sail, amazing snorkeling in secluded coves and just plain fun! Amenities include quality snorkel gear with expert instruction, sumptuous lunch and a thirst quenching open bar. Sailing St. Thomas, St. John and the Virgin Islands National Park with no more than six guests. Private parties welcomed. Wedding proposal, anniversary, birthday... we specialize in the celebration of great occasions and the every day! Visit our web site for more information!

  • Jester Sailing Adventures

    Classic Virgin Islands sailing at its best! Captain Jim and Jester have called these crystal clear waters home for over 20 years. Get the insider's tour of beautiful white sand beaches and colorful coral reefs with a captain who knows these islands best. You and your mates, family or new friends can relax and enjoy Captain Jim's freshly prepared BBQ lunch and luscious specialty libations- the tastiest in the business! Snorkel, swim and sail during half or full day trips for up to 6 people. Sunset sails available too. TripAdvisor Certificate of Excellence winner. Sailing Jester is the ideal Virgin Islands experience!

  • Goddess Athena

    Join us for unique adventures aboard our stunning, one-of-a-kind pirate ship! Queen of the Fleet for over 40 years, her 84 feet of classic lines make Goddess Athena a sight to behold. Friendly, knowledgeable crew, wonderful food and drinks, and sailing/snorkeling excursions tailored to your tastes will provide memories to last a lifetime. We invite you to experience the magic of sailing as only the pirates of the Caribbean knew. Our record 100% guest satisfaction speaks volumes. Join us today aboard the Goddess! Cannons by Request. Busty Wenches by Appointment Only. Sailing from Cruz Bay, St John.

  • Sail Island Girl Yacht Adventures LLC

  • Sail Island Girl Yacht Adventures LLC

    Come Sail Away aboard Island Girl, a 45 foot sloop! Maximum of 6 guests insures an intimate sailing and snorkeling adventure. Tradewind sailing at its best! Snorkel the pristine turquoise waters of the sunny Caribbean. Swim with sea turtles, rays, an abundant variety of sea life, corals, sponges, Caribbean fish, or even see a ship wreck. Havensight Dock arrival, we meet you where your ship docks, no taxi ride necessary. Crown Bay Dock arrival, a short taxi ride, approximately 5 minutes will get you to us. Captain Mike will whisk you away for your Caribbean Adventure! Half Day $75.00 pp, Full Day Sails $125.00 pp, Sunset Sails $65.00 pp.

  • Fury Sailing Charters

    SWIM WITH THE TURTLES SNORKEL/SAIL. Join the crew aboard the newly refurbished sailing yacht FURY for a 3.5 hour excursion to the National Marine Wildlife Refuge at Buck Island. Here you will encounter endangered Green Sea Turtles and a variety of sea life in their natural habitat. Day Sail on St. Thomas includes: snorkel gear, open bar, snacks, fresh water shower and free pickup and drop off at the Havensight Cruiseship Dock. Trips depart twice daily and can accommodate up to 25 guests. Voted #1 excursion activity on St. Thomas by Sunset sails available. Don't miss this very unique and popular wildlife excursion!

  • 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.

  • Tribal Daysails

    Tribal is a 40-foot trimaran specializing in custom tailored day charters, snorkel excursions, fishing, and sunset sails. The boat is a high performance racing trimaran designed for speed and comfort. The shaded cockpit can comfortably seat up to six guests for a more personal sailing experience. Hammocks and side nets also offer nice lounging areas to kick back right over the Caribbean ocean. Drinks and snacks are complementary all day. We also offer sunset sails. Experience a romantic sunset with an assortment of Hors d'oeuvres and a full open bar as you take in one of the most beautiful sunsets you will see in your lifetime. We specialize in sailing so make your reservation today!

  • Have a fantastic day of great sailing, lots of snorkeling, excellent service and delicious food! Our boats offer speed which enables us to explore more of St. John and islands around her. Expansive decks, shade awning and floats satisfy your need for comfort. We try to take you off the beaten path to some of those places you've dreamt about. And whether its snorkel instruction, beverage and food service or just telling tales our amiable crew will help make your day memorable, safe and fun. We offer full and half day trips, sunset sails, Sunday brunch and BVI trips.

  • Come aboard! Sail away with us for a day, and experience the perfect balance of adventure and relaxation aboard our sixty-four custom ketch. There is nothing like it! All you need is your towel! Swim, snorkel, sun or just relax as you sail the Caribbean in the unparallel spaciousness of your own private luxury yacht! There is no need to lift a finger; our warm, friendly, professional crew will pamper and entertain you. After all, it is your day! Call us to make a reservation for what will be the highlight of your trip!

  • Scubadu

    Scubadu is a 43 by 25 foot luxury Catamaran, specializing in private day, sunset, and/or dinner sailing excursions. Leave the crowds behind as you explore the beautiful waters, islands, and beaches of the U.S. Virgin Islands. We sail to beautiful snorkel and swimming spots you can't get to by car. Scubadu departs from Red Hook, St. Thomas or Cruz Bay, St. John. Because we only do private charters for a maximum of 12 people, we can customize your trip to your groups' needs. We provide the Captain, first mate, delicious food, beverages, snorkel gear, and fresh water showers. All you need to bring are towels and non-spray sunscreen.

  • Sail Wasabi

    Come sail aboard one of the most unique charter catamarans in the Virgin Islands. WASABI is a Stiletto 27 performance catamaran that specializes in fast, fun day sails. We sail the beautiful waters around St. Thomas and St. John. We explore the many beautiful anchorages, white sand beaches, off island cays, and coral reefs. We offer full & half day adventures with an open premium bar, deli style lunch with an array of choices, and premium snorkel gear and flotation. Let Captain Eric, a local Virgin Islander, be your guide and take you on a sailing adventure today.

  • Sail with Liberty Charters

  • Sail with Liberty welcomes you aboard for a memorable full day sail, half day sail, or sunset sail among the tropical islands, cays, and reefs of St. Thomas and St. John National Park on our beautiful Bruce Roberts Offshore 44' ketch. 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." We also offer exclusive sails and special discounts (see coupon). See our video and more info at

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  • Daysail Fantasy

    Join Captain Pam with a maximum of just six guests on her modern Pearson sloop for an exhilarating sail in the protected waters of the beautiful St. John National Park and surrounding cays. Fishing, sailing, amazing snorkeling, beachcombing, swimming with endangered sea turtles and a deliciously prepared hot lunch in the shaded cockpit. Open bar & Jimmy Buffet tunes. Snorkel gear provided, along with special floats and instruction, making it easy for all ages. Just $140 per person all inclusive. Voted Best Daysail St. Thomas 5 Years, Recommended By Trip Advisor, Frommers & Fodors.

  • Its Amasing Charters

    It's Amasing is a brand new 2016 45 ft Lagoon catamaran that is all set to take you on your exclusive Virgin Island excursions. Leave the crowds behind as we take you to our special snorkel spots. Departs from St. Thomas' East End or Cruz Bay, St. John. We only do private charters; choose a daysail or an overnight stay. Your Captain is Hollywood Joe, he's been in these islands for over 40 years & makes sure you have the best food & drinks. We have plenty of snorkel gear, and offer fresh water showers. All you need to bring are towels, sunscreen and your sense of adventure!

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