Caribbean Travel + St. Thomas + Activities + Sailing
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St. Thomas Sailing

Independence Saillboat Charter
Slip the lines, leave your cares behind, and experience the freedom of sailing the Caribbean with Captain Pat Stoeken on Independence, a 44' clipper-bowed ketch... more

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

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

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." Cast off for a classic daysail, beautiful scenery, and warm breezes on the crystal clear waters of the Caribbean... 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

Heavenly Days
Heavenly Days is a custom-built 53-foot catamaran... 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

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

On Deck Performance Sailing
Ondeck operates daily short course races on a multi million dollar racing sailboats... 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 1/2 day and full day sails, power snorkel excursions or sunset sails... more

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

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