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Jester Sailing Adventures

Learn Why Thousands have Experienced the Jester

Jester Sailing TShirt Back Cruising Da Virgins

Destinations

Jester sailing hosts guests from Cruise Ships

Fun Day Sailing & Sailboat Rental Charter -Highest Rated, Most Recommended, Award Winning Over 26 years BBQ Lunch & Open Bar, Sunset Dinner Cruises Best Snorkeling Spots

Charlotte_Amalie_Duty-Free_Shopping,_USVI

St Thomas Day Sail Charters

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St John Day Sail Charters

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Virgin Islands Day Sail Charters

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Our Services

Ask about Our Specialty Charters

Get This Deal

“Very Best Day of Our Entire Vacation – By Far“

Jester has been an operating charter sailboat in the Gorgeous U.S. Virgin Islands for TWENTY-FOURS (24) YEARS and we are Honored and Blessed to have hosted HUNDREDS of cherished and Raving-Fan Guests.

“Very Best Day of Our Entire Vacation – By Far” is the most heard comment from our cherished guests!

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