Sailing Adventure

Virgin Islands Sailing Adventures Sailboat Charter Rental St Thomas & St John US Virgin Islands – Sunset Dinner Cruise Sailing St Thomas St John Virgin Islands. Sailing St Thomas Virgin Islands are always full of fun and excitement.

Exclusive trip wanted?

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!

Our Philosophy

Set sail into your new life together with a Caribbean wedding in the Virgin Islands! Imagine just you, your mate and close friends sailing away to a tropical harbor for an intimate ceremony to be legally united by a Caribbean Captain… then toasting with champagne and hor d’oevers as the sun sets on the horizon. Or book a full day, get married on the bough of the boat, and start honeymooning in paradise!

Captain Rich is an ordained Minister with the Universal Life Church. Reverend Rich and Jester offer a romantic and memorable way to get married or renew your vows in the islands. You will not find more affordable and stress free wedding in the Caribbean. We can help you organize the tropical wedding of your dreams!

Achieve this Exclusive and Intimate Experience by Booking Direct and Saving!

For Over 20 years The Jester has been Providing Rest & Relaxation Experiences for Thousands of Chillin’-Starved People from All Over the Globe.

One of the longest running Jester Sailboats in the Virgin Islands Recommended!

With St Thomas Excursions, St John Excursions, Virgin Islands Excursions you even get fresh herbs on your freshly grilled lunch while you are out on your day sail
Go sailing with Jester and experience the Caribbean crystal blue waters and beautiful white sand beaches of St. Thomas. 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, or you can pick your favorite Virgin Island destination!

Fun Times With Jester Sailing

We had an awesome 1/2 day sailing with Rich and crew in January while on a cruise. Rich is experienced and a pleasure to be with. Wish we had booked a full day of sailing with him to see other islands. The cove where he is located makes for a delightful swim, too. Thanks Rich and Jester Sailing!


Great Day Sailing

My Girlfriend and I had a great day sailing with Jester and crew. They served a great lunch and the whole trip was just relaxing and adventurous. This was a highlight of our vacation and a great.value for the money. Thanks again for the taxi hookup they were


We are recommended by tripadvisor Award Winner Travel Agency

Sail Jester virgin island

Book Your Tour !

Jester Sailing Adventures

Jester Sailing Adventures in St. Thomas, US Virgin Islands

At Secret Harbour Resort - Eastend