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Jester Sailing Adventures

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St. Thomas, Caribbean
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About Jester Sailing Adventures
WE ARE SAILING AGAIN – OUR ISLANDS ARE BETTER THAN EVER AND THE SAILING AND SNORKELING IS FANTASTIC! Jester has received the coveted TripAdvisor Certificate of Excellence Winner EVERY YEAR TripAdvisor has given the award! Legendary Jester Sailing Adventures Virgin Islands offers Fun-filled Daysail adventures to St. John and the Virgin Islands National Park. Sail in the cool tropical breezes and explore the pristine white sand beaches and snorkel the colorful coral reefs. Relax and enjoy Your Captain's freshly prepared gourmet grub (fresh grilled lunch) and luscious specialty libations (ask about our exclusive and infamous "Jester Juice")! Conveniently located on the East End of St. Thomas at Secret Harbor - near most resorts and an easy ride from the cruise ship dock. Jester Sailing Adventures Virgin Islands and experience the very best of the Virgins!
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Hours Today: 8:00 AM - 8:00 PM
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fredsjamom wrote a review Jan 2020
Auburn, Michigan206 contributions116 helpful votes
Five stars to Captain Rich and Susan, 15 of us took a day sail when our cruise ship made port in St Thomas. We ranged in age from 4 to 83 and fun was had by all! The boat was clean, the music fit the island vibe, the beverages were plentiful, (Jester Juice was awesome), and lunch was great. We made two swim/snorkel stops, both were crowd free and had beautiful scenery and clear water. The boat had fins, masks, and snorkels for those who wanted them. There were also swim noodles for those who just wanted to float around. Captain Rich provided interesting info about the islands as we traveled along and he skirted around the afternoon showers which popped up. Finally as our day came to an end he allowed plenty of time so there was no concern about missing the all aboard time on our cruise ship. I highly recommend Jester Sailing especially if your looking for a great day on the water far away from the usual crowds!
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Date of experience: January 2020
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Djeremiah wrote a review Nov 2019
5 contributions
We had a delightful time with Rich and Jill! The sail was brilliant and beautiful. Memories made with our dear friends. We highly recommend this adventure. In addition, sailing out of Secret Harbour was a great location.
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Date of experience: October 2019
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Sheila M wrote a review Jul 2019
Charleston, South Carolina2 contributions1 helpful vote
We booked a 1/2 day sail for 6 aboard Jester, kind of last minute (one day’s notice), but Captain Rich and mate Jill were very responsive, and took great care to make sure we had a great day. I wish we had more time, as I would love to do a full day’s sail on Jester. Rich, Jill and crew mate Louis made sure we were very comfortable, safe and entertained. Captain Rich had many local “tidbits” to share during the sail and was careful to point out the best snorkeling spots in Christmas Cove, where we spent most of our time. Saw beautiful coral, fish and even a very large stingray; fascinating! My husband and I are very experienced sailors and really admired the way Rich handled the boat. Our “first time” sailing friends also enjoyed the trip very much. Jester is a beautiful classic-style 38’ Irwin, well-maintained and comfortable. There was a cooler that provided beer, soft drinks and water available throughout the sail. We had some snacks mid-trip, but the crowning glory was Jill’s amazing “Jester Juice” cocktail. It was even more delicious than our beloved Painkillers! We highly recommend Jester and her crew if you are looking for an excellent sail/snorkel experience. Ditch those over-crowded excursion boats and book Jester for a truly personal and pleasant day.
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Date of experience: July 2019
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D. Whitlock wrote a review Jun 2019
1 contribution
Booked a half day trip with Rich and Jill for my wife and I and had an absolutely amazing time! We toured around the islands, I got some snorkeling in while my wife sipped drinks from a floating bar off the boat, and sailed back to the harbor relaxing on the bow. Looking forward to our next adventure in October with them.
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Date of experience: June 2019
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stewart d wrote a review Jun 2019
Paris, Texas6 contributions1 helpful vote
Cap Rich and Jill were amazing. Cap Rich sailed us to different islands and gave us the history of each one. We anchored at a private beach area and while Rich and Jill prepared our lunch their skipper took us ashore to chill on the beautiful while sand beach. My husband swam with a logger head turtle which made his day. Back on board we were greeted with a fabulous lunch of pasta, chicken and corn on the cob.We would definitely sail with Cap Rich and Jill again. I highly recommend this excursion to everyone. One of the review questions was was it exciting and risky. It was great, exciting but never risky. Cap Rich and Jill took excellent care of us. Debbie and Stewart Tyler Texas June 2019
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Date of experience: June 2019
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