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Jester Sailing Adventures
![Jester Sailing TShirt Back Cruising Da Virgins Jester Sailing TShirt Back Cruising Da Virgins](https://sailjester.com/wp-content/uploads/2023/12/Jester-Sailing-TShirt-Back-Cruising-Da-Virgins.gif)
Destinations
![Jester sailing hosts guests from Cruise Ships Jester sailing hosts guests from Cruise Ships](https://sailjester.com/wp-content/uploads/2023/12/Jester-sailing-hosts-guests-from-Cruise-Ships-scaled.jpg)
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 Charlotte_Amalie_Duty-Free_Shopping,_USVI](https://sailjester.com/wp-content/uploads/2023/12/Charlotte_Amalie_Duty-Free_Shopping_USVI.png)
St Thomas Day Sail Charters
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![St John US Virgin Islands St John US Virgin Islands](https://sailjester.com/wp-content/uploads/2023/12/St-John-US-Virgin-Islands.jpg)
St John Day Sail Charters
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![Buck Island US Virgin Islands Buck Island US Virgin Islands](https://sailjester.com/wp-content/uploads/2023/12/Buck-Island-US-Virgin-Islands.jpg)
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
Enjoy Luxury
Your Destination Choices
![White Bay Jost Van Dyke, BVI](https://sailjester.com/wp-content/uploads/2023/12/White-Bay-Jost-Van-Dyke-BVI.jpg)
Christmas Cove, Great St James Island Bay
![St John US Virgin Islands](https://sailjester.com/wp-content/uploads/2023/12/St-John-US-Virgin-Islands-1.jpg)
Trunk Bay, St John, US Virgin Islands
![Anegada Island BVI](https://sailjester.com/wp-content/uploads/2023/12/Anegada-Island-BVI.jpg)
Caneel Bay, St John, US Virgin Islands
![Scrub Island BVI](https://sailjester.com/wp-content/uploads/2023/12/Scrub-Island-BVI-scaled.jpg)
Buck Island (& Capella) St Thomas, US Virgin Islands
![St Thomas US Virgin Islands](https://sailjester.com/wp-content/uploads/2023/12/St-Thomas-US-Virgin-Islands.jpg)
Magens Bay, St Thomas, US Virgin Islands
![Tortola British Virgin Islands](https://sailjester.com/wp-content/uploads/2023/12/Tortola-British-Virgin-Islands.jpg)