Captains Mates and the Boat

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


You will not find a more easy going, affable and accommodating skipper than Captain Rich. Originally from Florida, Rich has lived in the Caribbean for over 11 years and has extensively sailed throughout the islands.

As a US Coast Guard licensed Master Captain and PADI Driver, Captain Rich will safely sail you to any of the awesome Virgin Island anchorages and beaches. Captain JIM Sailing local knowledge can take you to the perfect island paradise location.

Whether you wish to take a turn at the helm and learn to sail or just kick back and relax with an island cocktail, Captain Rich will no doubt show you the very Jester is a sleek and impressive 38 ft. sloop. You will be provided best boat Captain St Thomas for your trip she is both fast and a joy to sail. There is a comfortable cockpit as well as a huge cushion on the fore deck to kick back and soak up the sun and the scenery. Jester is a fully equipped vessel with a private head, fresh water shower, easy access swim ladder, top quality snorkel and fishing gear, floats, a strong dingy for exploring, and always great tunes!


Jester is a fiberglass 38 ft. sloop rig racer/cruiser, built in 1988 by Irwin Custom Yachts in Clearwater, Florida.


Amenities and Specifications:

  1. Private head with fresh water shower
  2. Full galley with icebox and propane stove/oven
  3. 90 gallon fresh water capacity
  4. Comfortable sleeping for up to six guest guests
  5. Private cabin with large double berth
  6. Dinette converts to double berth
  7. Dingy: 12′ Hard bottom inflatable w/ 25 hp outboard
  8. Complete safety gear and VHF Radio
  9. Depth and speed instruments
  10. Length: 38 ft.
  11. Beam: 12’6”
  12. Draft: 4’11” (wing keel)
  13. Displacement: 15000 lb. (uncapsizable)
  14. Sail Area: 675 sq .ft.
  15. Full Mainsail and Rollerfurling Jib
  16. Engine: Inboard 27 hp 3 cylinder Yanmar diesel
Amenities and specifications.

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Sail Jester virgin island

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Jester Sailing Adventures

Jester Sailing Adventures in St. Thomas, US Virgin Islands

At Secret Harbour Resort - Eastend