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

Contact Sail with Liberty Charters

Contact Seas the Day Charters and Tours

Contact Stormy Pirates Boat Charters

Contact Independence

Contact Max Charters

Contact Sailing the Cosmos Charters

Contact Sweet Pea Catamaran Charters

Contact Fury Sailing Charters

Contact Catania Yacht Charters

Contact Son of a Sailor Charters


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