All Aboard! Come Sailing with Jester

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Snorkel right off the bow of the boat

Snorkel Excursions

Come sail in cool tropical breezes and snorkel and explore the colorful coral reefs!

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Meal included in Full Day Sail

Full and Half Day Sails

Sure to be one of your most memorable days of your vacation. We will hoist the sails and let the warm tropical breezes carry us away!
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Have Captain Jim officiate your wedding!

Island Weddings

Set sail into your new life together with a Caribbean wedding in the Virgin Islands!
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FULL DAY SAILS ~ HALF DAY SAILS ~ SUNSET CRUISES ~ SNORKEL EXCURSIONS ~ ST. JOHN and the Surrounding Cays ~ PRIVATE and CUSTOM SAILING CHARTERS

Daysailing and Chartering in St. John and the Surrounding Cays

Sail Jester and experience the Caribbean crystal blue waters and beautiful white sand beaches. Come sail in cool tropical breezes and snorkel and explore the colorful coral reefs. Daysail charters are offered to the Virgin Islands National Park in St. John, or you can pick your favorite Virgin Island destination!

Aboard Jester, guests are welcome learn to sail or just kick back and relax in the comfortable cockpit or lay out on the huge cushioned foredeck and soak up the sun and awesome scenery. All sailing trips include great gourmet grub, Captain Jim’s luscious specialty libations and always some super tunes to set the mood! Jester is fully equipped with a private head, fresh water shower, easy access swim ladder, float mats, top quality snorkeling gear and instruction, and fishing gear too!

Come and join Captain Jim and Jester for a great day of sailing and fun and make the best of your Virgin Islands vacation by adding in a sailing charter from Jester Sailing Adventures!