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
Captain Max
Looking for an unforgettable day on your Caribbean vacation, come join Captain Max on her classic 41’ sloop LOU. With Captain Max you will sail... (More)
Looking for an unforgettable day on your Caribbean vacation, come join Captain Max on her classic 41’ sloop LOU. With Captain Max 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. Lou 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!
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... (More)
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.
Sweet Pea Catamaran Charters
Sweet Pea Catamaran Charters - Private Catamaran Charters available for up to 12 guests. The 40’ Catamaran features Two large trampolines for lounging, fully shaded... (More)
Sweet Pea Catamaran Charters - Private Catamaran Charters available for up to 12 guests. The 40’ Catamaran features Two large trampolines for lounging, fully shaded cockpit, gourmet freshly prepared lunch, full premium bar, guided snorkel tour, quality snorkel gear, fresh water showers, two heads and a crew that is exceptional at making this the best day of your vacation. Please bring Towels, sunscreen, and cameras. We can vary the details to suit your day.
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... (More)
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!
Son of a Sailor Charters
At Son of a Sailor Charters we provide you and your family with an all-inclusive adventure. We offer Sail and Snorkel Cruises, Romantic Sunset Sails,... (More)
At Son of a Sailor 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... (More)
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.
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... (More)
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.
