St. Thomas’ wonderful weather and beautiful scenery offer perfect conditions for sailing. St. Thomas island and its Yacht Club hosts multiple sailing regattas throughout the year, and has produced champion sailors. Since you are visiting an island so well regarded for sailing, what are you waiting for – Go Sailing! Whether you’re a landlubber that wants to have a relaxing sailing excursion where you are pampered with open bar and lunch; stop at a few quiet coves and snorkeling spots; and if you’re lucky swim with turtles. Or you are an avid, seasoned sailor that wants to get in on the sailing action for which the island is renowned. Either way, your day out sailing is sure to be a favorite memory of your St. Thomas vacation. Many sailing charters cater to groups of 6 passengers, and there are larger boats for bigger groups. Charters are available in half day trips and full day. Sunset sails are also an option and a fantastic way to enjoy the tranquil beauty and romance of Caribbean evenings. Visit the featured charters below for more information.
Featured Sailing Charters
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!
Daysail High Pockets Information Request Form
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.
Independence Information Request Form
It's 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!
It's Amasing Charters Information Request Form
Daydreamer & Coconut
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.
Daydreamer & Coconut Information Request Form
Sail with Liberty Charters
Sail with Liberty 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, 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." See our video and more info at sailwithliberty.com.
Sail with Liberty Charters Information Request Form
Oh Be Joyful Sailing
Sail away with Oh Be Joyful Sailing for an unforgettable excursion of sailing, snorkeling, and discoveries in the most beautiful waters of the Caribbean. Board the fabulous sloop Bavaria 44 Ocean Spirit on either St. Thomas or St. John. Full day, half day and romantic sunset sails available. Enjoy an excursion to St. John and nearby islands of Pillsbury Sound. Plenty of room to relax in the shaded cockpit or soak up the sun on our spacious decks. The luxurious cabin downstairs is great for a nap! We provide satisfaction, and one of the nicest days of your vacation. TripAdvisor Excellence Awardee.
Oh Be Joyful Sailing Information Request Form
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.
Scubadu Information Request Form
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.
Catania Yacht Charters Information Request Form
New Horizons Daysails
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!
New Horizons Daysails Information Request Form
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 Tripadvisor.com. Sunset sails available. Don't miss this very unique and popular wildlife excursion!
Fury Sailing Charters Information Request Form
Join Captain Chris for a wonderful, relaxing day of sailing and snorkeling on EDEN a 37 foot Tartan sailboat. Our first snorkeling location is Buck Island, a National Marine Wildlife Refuge. Explore coral reefs, snorkel over a ship wreck and see more beautiful fish than you can imagine. After a healthy snack we sail to Water Island and to Bill's secret cove for lunch, more snorkeling and beach exploring. Fabulous lunch/open bar/ shaded cockpit/ guided snorkeling tours (with instruction if needed). Departs from downtown St. Thomas. Six guests max. Half day tours $85 per person/Full day$135 per person $120 for children 12 and under.
Sail Eden Information Request Form
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!
Tribal Daysails Information Request Form
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.
Goddess Athena Information Request Form