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Jester Sailing Adventures

Jester Sailing TShirt Back Cruising Da Virgins


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

St Thomas Day Sail Charters
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St John US Virgin Islands
St John Day Sail Charters
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Buck Island US Virgin Islands
Virgin Islands Day Sail Charters
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Our Services

Ask about Our Specialty Charters

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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Planning & Scheduling

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Your Destination Choices

Christmas Cove, Great St James Island Bay

Trunk Bay, St John, US Virgin Islands

Caneel Bay, St John, US Virgin Islands

Buck Island (& Capella) St Thomas, US Virgin Islands

Magens Bay, St Thomas, US Virgin Islands

Maho Bay, St John, US Virgin Islands