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

Contact Catania Yacht Charters

Contact Sweet Pea Catamaran Charters

Virgin Islands Day Sailing

Contact Virgin Islands Day Sailing

Contact Sail with Liberty Charters

Seas the Day Charters and Tours

Contact Seas the Day Charters and Tours

Contact Grateful Day Charters

Contact Max Charters

Contact Fury Sailing Charters

Sailing the Cosmos Charters

Contact Sailing the Cosmos Charters

Contact Independence

Stormy Pirates Boat Charters

Contact Stormy Pirates Boat Charters

Contact Yacht Rock Charters

Contact Rumbaba Charters


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.

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