Jester Sailing Adventures

St. Thomas, U.S. Virgin Islands

5

3 reviews

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Telephone:
+1 340-513-2459
Address:
St. Thomas, Virgin Islands 00802
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Today

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Local time (St. Thomas) 7:26 PM Monday, June 16, 2025

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Description

Specialties

Daysails and Chartering in the U.S. Virgin Islands

Come sail away with Jester Sailing Adventures and experience the Virgin Islands at it’s best!

~ Full & Half Day Sails ~ Sunset Cruises ~ Snorkel Excursions ~ St. John & surrounding cays ~ Weddings ~ Private & Custom Charters ~

Sail Jester and experience the crystal blue Caribbean waters and beautiful white sand beaches of the Virgin Islands. Come sail the tropical breezes and snorkel and explore the colorful coral reefs.

Daysail charters are offered to the Virgin Islands National Park in St. John and surrounding cays or you can pick your favorite Virgin Island destination! All sailing trips include great gourmet grub, Capt’n Jim’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, and top quality snorkeling gear and instruction.

Make the best of your Virgin Islands vacation with a sailing charter from Jester Sailing Adventures!

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3 reviews of Jester Sailing Adventures

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Place rating: 5
Washington, DC
This review is long over due. I went on a trip in November 2011 to St. Thomas and this was the best part of the trip. We had the entire boat to ourselves and it was a breathtaking trip. The sailing part was great and the Captain was very friendly and even cooked us lunch. I would definitely recommend Jester for your next sailing adventure if you’re ever in the St. Thomas area. He made our trip better than expected and we got lucky having the entire boat to ourselves.
Place rating: 5
Marietta, GA
The greatest part of the trip. Captain Jim was better than ever could be expected. Celebrated a birthday on the boat and he brought a birthday cake on board as a surprise. Expensive, but worth every penny. It was a chance of a lifetime. Thanks Captain Jim
Place rating: 5
Katy, TX
The first thing we knew we wanted to do when we planned our trip in St. Thomas was to take a day sailing trip. We scoured the internet, but didn’t have a ton of luck finding info. We finally read about Jester Sailing and emailed him. He was very helpful and explanatory and we decided to book it. His boat is a 38′ sailing boat and holds up to 6 people. We decided to book the entire boat for the 4 of us so that it wouldn’t ever feel crowded though.
We met him in on the beach of Secret Harbor at 10am and he took us out to the boat in his dingy. It was a gorgeous day and I knew it was going to be a fantastic time. He started us all out with a morning cocktail and my friends raved over his famous «Jester Juice» cocktail. (I’m not a fan of coconut so I had a rum punch and it was awesome too!) We headed over to Honeymoon Bay on St. John and spent some time on the beach, did some snorkeling and saw a sting ray. At lunchtime, he came and picked us up again on the dingy and brought us back to the boat. He had grilled some chicken and had a pasta salad and corn with it. It was awesome! He said for many years, he’d been in restaurnant management as well, so that explains why he’s such a great cook!
After Honeymoon Bay, we headed over to Christmas Cove and did more snorkeling– there were tons of fish! He dove down and found a conch on the ocean floor and pointed out lots of fish I would have totally missed! I hated having to come back in to shore, but it was truly the perfect day and Jim did such an excellent job.