Call or Text: 340-201-3325 [email protected]
Select Page

Book The Exciting Legendary…

Jester Sailing Adventures

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
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Donec sed finibus nisi, sed dictum eros.
St John US Virgin Islands
St John Day Sail Charters
Quisque aliquet velit sit amet sem interdum faucibus. In feugiat aliquet mollis etiam tincidunt ligula.
Buck Island US Virgin Islands
Virgin Islands Day Sail Charters
Luctus lectus non quisque turpis bibendum posuere. Morbi tortor nibh, fringilla sed pretium sit amet.

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!

Plan a Trip Today

Get a Quote

Planning & Scheduling

Enjoy Luxury

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