Day Charter Sailboats in the Virgin Islands

Sailboats are a great way to experience the stunning waters of the Virgin Islands, in a natural, relaxing, and eco-friendly manner. These boats offer a traditional sailing experience and use sails to capture the consistent winds of the Virgin Islands to propel you to your next destination. See below for a featured selection of day charter sail boats that we represent, or contact us now to find the perfect sailboat for your next trip.

Cloud 9

Cloud 9 is the ideal choice for guests who want an intimate sailing experience around uninhibited and private islands near St John or a day sail over to Jost Van Dyke. This boat is also a great choice for private groups that include both scuba divers and snorkelers (the only sail boat on St John to offer guided scuba diving).

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Survivan

Set sail aboard one of the USVI's most spacious and well maintained boats. Great for families seeking a day of sailing, sun, and spacious luxury.

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Cimarron Yacht Charters

Join Capt Rick for a day of purist sailing on the gorgeous waters of the US and British Virgin Islands. With only 6 total passengers, guests will experience luxury sailing with a long-time captain.

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Kekoa

One of St John and the USVI's most recognized and loved catamarans, Kekoa's known for her class-act crew and gorgeous vessel. Snorkeling equipment provided.

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Daydreamer/ Coconut

These sister catamarans are spacious and luxurious, and are equally great for romantic sunset sails as they are for full day fun.

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Sail Pepper

Enjoy tranquility- and a gourmet lunch- as you sail the quiet waters of Coral Bay on Pepper, a classic wooden sloop rich with St John history.

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Calypso

Enjoy a spacious, smooth sailing experience aboard one of the VI's most popular sailboats. Regularly scheduled sailings to Jost Van Dyke and St John's famed north shore offer guests easy access to the best of the Virgin Islands.

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Kiote

Sail out of Coral Bay with Capt Jimmy on a full or half day sail. When conditions allow, join Kiote for the unique sunrise or full moon sails- the only boat on island to offer these special sailings.

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Island Girl

This traditional wooden sailboat is conveniently located in the Charlotte Amalie harbor, making a day spent on the water with Island Girl and Capt Mike an easy option for resort guests and cruise ship passengers alike.

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Treazzure Sailing

Sail with Capt Joe "Hollywood" aboard Treazzure, as classic, luxurious 60' ketch. Numerous pick up locations and a premium open bar.

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Day Sail Fantasy

Join Capt Pam as she sails guests to some of the most beautiful beaches and snorkeling spots in the world. Full day sails include a gourmet lunch.

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New Horizons Sailing

Set sail with this spacious, 65' sloop. Offering full day sails to the waters off St John, as well romantic sunset dinner cruises. All trips are open bar.

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