St. Thomas Sailing

Adventure Classic Winifred
Daysail Caribbean Style on the classic charter boat Day Sail Yacht Winifred from St. Thomas, U.S. Virgin Islands to the St... more

Blue Tang Yacht Charters
Come aboard the Blue Tang and experience a day of luxury and adventure. Island-hop with our certified captain and experienced crew while enjoying great food, snorkeling, and a yacht full of fun... more

Captain Max
Join the famous Captain Max on the S/V "Lou," a classic 41' Rhodes Bounty II sloop, for an unforgetable day of sailing, snorkeling and fun on St. John and the surrounding islands... more

Castaway Girl Catamaran
Experience the thrill of sailing aboard the fabulous 65' catamaran "Castaway Girl... more

Daysail Fantasy Sail to The St. John National Park and surrounding cays. Swim, Snorkel, Beach comb, or just relax under a shade awning. Avoid the Crowds ~ Personal attention given to no more than 6 guests... more

Daysail High Pockets
Daysail aboard the sleek and beautiful, classic sloop High Pockets, family owned and operated since 1970. She is a forty-two foot sloop, originally designed for racing... more

Fair Wind Sailing School
Fair Wind Sailing School operates in the Virgin Islands with sailing lessons running from November through July. Our sailing base is in St. Thomas, U. S... more

Fury Charters
Swim with the turtles on one of our day sails, enjoy a cocktail on a romantic sunset cruise, or charter the boat privately... more

Ike Witt Charters
Sail aboard the Caribbean yacht charter, the "IKE WITT". Captain Pat will amuse you with Pirate's of the Caribbean sailing stories, folk lore and life on the Islands... more

Island Sol
At Island Sol we understand the need for instant satisfaction, that's why we offer the thrill of sailing on your own in just 1 lesson! Sign up for our Sailing Program and within an hour you will be d... more

Jester Sailing Adventures
Full-day sail excursions offered daily from 10am to 4pm... or set your own times..... more

Jolly Mon Iguana Sailing Charters
Experience the elegance and performance of sailing the Classic 48' yawl, Jolly Mon, as we explore the quiet coves and cays around St. Thomas. Come sail and snorkel with a maximum of 6 guests... more

Morning Star Charters
Join Captain Jake Morganstern on Morningstar, a 42' Cheoy Lee sailboat, for a day of Caribbean snorkeling and day sailing around St. Thomas and St. John, U.S. Virgin Islands... more

New Horizons
Sunset dinner cruise: We board from Sapphire Beach Resort Marina at 5:00pm... more

Oh Be Joyful Sailing
Sailing aboard the 45 foot Johanna Augusta II, you will enjoy the thrill of sailing, in a comfortable and safe sailing vessel. We sail daily for a full day, half day, or romantic sunset sail... more

Rumbaba Charters
For the finest day sail experience in the Virgin Islands come sailing on Rumbaba * full day sails * half day sails * sunset sails * private and custom charters All cruises feature... more

Sail Island Girl
For your pleasure we offer ½ day and full day sails, power snorkel excursions or sunset sails... more

Scubadu
Scubadu is a luxury Catamaran, specializing in private sailing excursions in the USVI and British Virgin Islands. Trips aboard Scubadu are tailored to your needs... more

Treazzure
Treazzure, a 60' classic beauty offers lush contemporary comfort with plenty of room to relax and have fun... more

Yacht Nightwind
Daysail from St Thomas Island aboard a classic wooden boat meticulously maintained to the highest standards and the best of all worlds! We offer the ease of dockside boarding at Sapphire Beach Mari... more

Add New St. Thomas Sailing Listing Here »