Highest Rated & Most Recommended Charter Company in the Virgin Islands -for over 24 Years!

Welcome to the Legendary Jester Sailing Adventures

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All Inclusive Sailing Excursions St Thomas Yacht Charter & St John US Virgin Islands

  • Full Day Sails
  • Half Day Sails
  • Sunset Cruises
  • Snorkel Excursions
  • St. John and the Surrounding Cays
  • Private and Custom Sailing Charters
  • Cruise Ship Excursions St Thomas Sailing
  • Virgin Islands Excursions

Our Facilities & Services Us Virgin Islands

Virgin Islands Sailing Adventures Sailboat Charter Rental St Thomas & St John US Virgin Islands – Sunset Dinner Cruise Sailing St Thomas St John Virgin Islands


 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! Full Lunch & Open-Bar


A quick sail over to Christmas Cove on St. James. Swim or snorkel with turtles and rays and enjoy the sun. Includes snacks and Open-Bar


 There is nothing quite like sailing into a stunning gorgeous Caribbean sunset 2 hour sail, always open bar and appetizers


Many various cuisine to choose from including standard American, Thai, Indian, French, Italian and far More - plus Oepn Bar and other specialties


What could be better than celebrating your new future with a group of your closets friends?!


Easily build employees' moral and staff loyalty with fabulous days at sea - great for those all-important meetings as well!

Daysailing and Chartering Excursions in and around St Thomas & St John and the Surrounding Cays


Sail Jester Sailing Adventures Charter St Thomas John Virgin Islands and experience the Caribbean crystal blue waters and beautiful white sand beaches. You can also enjoy St Thomas Yacht Charter and gather the memories. 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 and Virgin Island Sailing Charter is always awesome or you can pick your favorite Virgin Island destination!

Experience Luxury

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 Rich’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 and you can also plan USVI Honeymoons.

Jester Sailing Adventures

Jester Sailing Adventures St Thomas, US Virgin Islands at Secret Harbour Resort

Offering a Wide Variety of USVI Honeymoons, Vacation Fun, Relaxation & Shore Excursions…

Watch Sailing & Snorkeling Fun Videos Below to Learn More and Book Now…


No one does lunch better! If you’re fed lunch on other charters, its simple lunch-meat sandwiches and potato chips – We’re different!

The smell of saltwater in the air, the wind rising to greet you, and the marvel of an endless horizon – True Nautical Paradise

Experience the crystal blue Caribbean waters, snorkel and explore colorful coral reefs and see underworld critters of USVI

Our home-base bay – moored at clearing the very best overall beach on all of St Thomas Sailing, USVI -Secret Harbour

We are recommended by tripadvisor Award Winner Travel Agency

Certificate of excellence
Certificate of excellence
Certificate of excellence
Certificate of excellence
Certificate of excellence
LTG Winner
LTG Winner
LTG Europe Winner
Sail Jester virgin island

Book Your Tour !

Jester Sailing Adventures

Jester Sailing Adventures in St. Thomas, US Virgin Islands

At Secret Harbour Resort - Eastend