Jester Sailing Adventures

Jester Sailing Adventures, St. Thomas: Hours, Address, Jester Sailing Adventures Reviews: 5/5

Jester Sailing Adventures
Scuba & Snorkelling • Boat Tours
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8:00 AM - 8:00 PM
8:00 AM - 8:00 PM
8:00 AM - 8:00 PM
8:00 AM - 8:00 PM
8:00 AM - 8:00 PM
8:00 AM - 8:00 PM
8:00 AM - 8:00 PM
8:00 AM - 8:00 PM
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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!
St. Thomas, U.S. Virgin Islands
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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.

560 reviews
Very good

Auburn, MI207 contributions
Jan 2020 • Family
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!
Written January 5, 2020
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

5 contributions
Oct 2019
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.
Written November 5, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Sheila M
Charleston, SC4 contributions
Jul 2019 • Couples
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.
Written July 21, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

D. Whitlock
1 contribution
Jun 2019 • Couples
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.
Written June 20, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

stewart d
Paris, TX6 contributions
Jun 2019 • Couples
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
Written June 9, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

3 contributions
Mar 2019 • Couples
What a great adventure ... I started sailing a year ago and wanted to experience a monohull in the Carribean. Capt Rich and Jill not only took us on the adventure of our life time but they let me sail their 38 Foot JESTER! Wow They are just the best ! Please come see them when in St Thomas. They have a 40 foot catamaran Zun Zun and a 38 foot monohull. We snorkeled, sailed and snacked our way through the islands.

What’s a great humble couple that enjoy serving their clientele !

Thanks again Team Jester !!
Written April 28, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Cranston, RI4 contributions
Feb 2019 • Couples
Such an amazing day and perfect location! We we're staying at an Air Bnb right at the top of Secret Harbour, so when I found Jester, I didn't hesitate to book.

First off, my boyfriend and I have never been sailing before, so Captain Rich and Jill were very informative and made us feel very comfortable. On top of that, they could've rescheduled us for the next day (since they had to with 2 other couples due to the weather the day before), however, it was a gorgeous day out and they decided to let us join them on their daily leisure excursion and we ended up having the entire boat to ourselves! They didn't have to do that, but they knew we were leaving the following thank you again Captain Rich for doing that!

We sailed around the islands...amazing views! Breath-taking. And we anchored down for some snorkeling, lunch and drinks, all which was fantastic. Captain Rich knows all of the cool snorkeling spots and was able to tell us about the islands...very knowledgeable.

They even have a Catamaran they is joining their we can't wait to go back to St. Thomas and stay with them for a few nights, or maybe enjoy a spa day on their new gem 🤩
Written March 19, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Trey T
Boston, MA4 contributions
Mar 2019 • Friends
My three friends and I embarked on a long weekend to St. Thomas. Rich and Jill were fantastic through and through. We ended up doing two full days with them (One on Jester and one on ZunZun). Jester is the sail boat, which Rich says, “Is all about the journey, not the destination.” The ZunZun is the catamaran. Rich was conscious of us being with him for the back to back days, so we went to different spots. The lunch is top notch, beer is ice cold, and each boat has a signature drink (just mix in a water.. so you don’t drunkenly fall of the ‘bow’).
Written March 8, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

1 contribution
Jan 2019 • Couples
My wife Milena & I had a wonderful day sail on the Jester. Captain Rich was fantastic & Jill & crew were great. The food was amazing & the Jester Juice was very tasty & not too strong. The day was beautiful for the sail to St John for snorkeling. We stayed over there for a very nice lunch & met a nice couple from Oklahoma. It's always cool to meet new people from different parts of the U.S. I've done other sails in St Thomas & St John & this was the best by far.

Rob & Milena Emery
Brooklyn NY
Written February 25, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Fort Worth, TX47 contributions
Dec 2018 • Couples
I truly almost never write bad reviews but our experience on the Jester was less than acceptable from the start.
As with other reviewers, my husband and I took a day sail on the Jester with the previous owner (Jim). We had a marvelous time. We visited 3 snorkel spots as well as a wonderful gourmet barbecue lunch.
Remembering this sail, we decided to treat some very good friends to a “private” day sail. My husband had e-mailed the Jester and Jim asking to book for 4 from a cruise ship. In none of the correspondence did the current owners explain there was a change in ownership. There were a couple of emails back and forth and we were booked. We were very excited to take our friends on this excursion.

We should have realized the day was going to be less than impressive when we arrived at the beach (where the Jester is moored) to find NOBODY there to meet us. After 2 phone calls my husband left a message to ask what was the problem. He was finally contacted by Rich (at this point we still did not know he was the new owner) stating they thought we were not coming (even though my husband had several emails to confirm our reservation) and would be an hour late.
Jill and Rich finally show up dragging provisions for the trip.

I could go on and itemize the multiple ways we were disappointed, from the STALE snacks served, to broken sails and the inability to sail on a SAILBOAT, chips poured from a bag at the table and salsa dumped in to a drinking cup. My favorite part was being served pizza from a box on paper plates for our gourmet lunch. They had no mixers for drinks, even though an open bar was included. We visited only one snorkel spot.

Needless to say our daysail was not what we were hoping for. It was not the day we had planned to share with our friends.
After getting back and some consideration, my husband contacted Rich to ask for a small partial refund sighting the above and more. He agreed that they were not quite on their game that day, but felt that the beer cozies with the boats logo on it, would make up for the deficiencies, but understood how we felt and would send a refund check. After waiting a month, we contacted Rich again to inquire about the refund. His response began with “Hi Dan” even though my husbands name is Bob. He gave excuses why the check had not reached us and promised to send another. Obviously, we are still waiting.

But we are doing our share. His robo email asked us to write a review. So here it is.
Written February 21, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

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