Virgin Islands Sailing Adventures

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

Excursions offered daily from 9am to 3pm... 10am to 4pm… or set YOUR OWN times… it’s your day!

Sailing from beautiful Secret Harbor and partnered with Aqua Action Dive Shop, we are conveniently located on the east end of St. Thomas near most major hotels and just an easy ride from the cruise ship dock. You can enjoy coffee and breakfast at the Sunset Grill Cruzan Beach Club before taking an invigorating sail through the beautiful tropical waters to St. John and the surrounding islands and cays. Swim and snorkel off the colorful coral reefs. Relax and play on the pristine white sand beaches. Enjoy a freshly prepared BBQ lunch of our tasty voodoo chicken, rasta pasta salad, and buttery corn on the cob, and sip on unlimited ice cold beverages and specialty libations…you’ll love the “Jester Juice”! After an afternoon of great food, snorkeling, swimming and fun…just kick back and relax to an easy down wind sail back home to St. Thomas and enjoy our freshly prepared chips & mango salsa.

Just a taste of the exciting Adventures that wait you aboard Jester Sailing:

FULL DAY SAIL - 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!

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

HALF DAY SAIL - A quick sail over to Christmas Cove on St. James. Swim or snorkel with turtles and rays and enjoy the sun. Morning or afternoon trips are available, and you can enjoy our open bar and tasty snacks

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

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

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

DESTINATION ISLAND WEDDINGS & HONEYMOONS ABROAD


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.
jester sailboat from above

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One of the longest running 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!
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