Jester Sailing Adventures
Jester Sailing Adventures
5
8:00 AM - 8:00 PM
Monday
8:00 AM - 8:00 PM
Tuesday
8:00 AM - 8:00 PM
Wednesday
8:00 AM - 8:00 PM
Thursday
8:00 AM - 8:00 PM
Friday
8:00 AM - 8:00 PM
Saturday
8:00 AM - 8:00 PM
Sunday
8:00 AM - 8:00 PM
Full view
About
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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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
5.0
560 reviews
Excellent
539
Very good
12
Average
3
Poor
0
Terrible
6
fredsjamom
Auburn, MI206 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. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
futurefile
Radnor, PA53 contributions
We arrived at Fungi's restaurant, a dockside bar at the bottom level of the Pt. Pleasant Resort, around 10 am for our trip. Captain Jim pulls up in his dinghy, introduces himself, and we are off for the Jester anchored a few yards away.
Captain Jim is a very relaxed and accomodating man who made us, four people on our trip, feel at home. The beverages flowed freely, with the Jester Juice, a pina colada type concoction, being a very tasty and refreshing choice.
The views from the Jester were fabulous on the trip which started in St. Thomas and wound through St. John and other isles between.
The snorkeling was average for the Caribbean, at least on that beach. That means it was very pretty and a variety of reef fish were present, including a sting ray. If you just want to swim to the flawless white sand beach instead, go for it. Lunch followed with a Caribbean chicken recipe, pasta, and corn on the cob. We sailed afterwards through more isles that afternoon, a perfect day, with the Captain allowing me to take the helm on the way back. That was fun. Blue skies, the wind and tropical isles dotting the waterscape, made for a relaxing day. We got back to port feeling quite happy with spending our day aboard the Jester.
If you want to spend it with a dozen or more others, take the New Horizon or other large boats we saw anchored while we snorkeled. If you want a more intimate and quiet relaxing day of sailing the Caribbean, take the Jester Daysail.
Captain Jim is a very relaxed and accomodating man who made us, four people on our trip, feel at home. The beverages flowed freely, with the Jester Juice, a pina colada type concoction, being a very tasty and refreshing choice.
The views from the Jester were fabulous on the trip which started in St. Thomas and wound through St. John and other isles between.
The snorkeling was average for the Caribbean, at least on that beach. That means it was very pretty and a variety of reef fish were present, including a sting ray. If you just want to swim to the flawless white sand beach instead, go for it. Lunch followed with a Caribbean chicken recipe, pasta, and corn on the cob. We sailed afterwards through more isles that afternoon, a perfect day, with the Captain allowing me to take the helm on the way back. That was fun. Blue skies, the wind and tropical isles dotting the waterscape, made for a relaxing day. We got back to port feeling quite happy with spending our day aboard the Jester.
If you want to spend it with a dozen or more others, take the New Horizon or other large boats we saw anchored while we snorkeled. If you want a more intimate and quiet relaxing day of sailing the Caribbean, take the Jester Daysail.
Written June 6, 2005
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
How very kind of you to make our Captain Jim blush so much... guess that means he is flattered - so are we. Thank you for your wonderful comment and please come Sail with The Jester again.
Written May 23, 2017
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
captmike
Cape May, NJ22 contributions
I chartered Capt. Jim for 1/14/2006 after reading the great reviews here at Tripadvisor, taking my wife and two kids (12,9). I'm in the charter business and can be very critical, but Jim runs a first class trip and deserves the praise and high marks that he has earned at tripadvisor.
I won't bother listing all the details of this fantastic trip, except to say that Jim's attention to detail, customer service, and friendliness were the keys to this great day.
This is the best way to go for a sail, snorkel, or great time while in St. Thomas. I would (and will) recommend Jester Sailing Adventures to everybody.
Like others have said, my only regret is that I booked him for only one day. When I go back down, I won't make that mistake again.
I won't bother listing all the details of this fantastic trip, except to say that Jim's attention to detail, customer service, and friendliness were the keys to this great day.
This is the best way to go for a sail, snorkel, or great time while in St. Thomas. I would (and will) recommend Jester Sailing Adventures to everybody.
Like others have said, my only regret is that I booked him for only one day. When I go back down, I won't make that mistake again.
Written January 18, 2006
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
mylanta
atlanta, ga12 contributions
I had reservations with Capt Jim for a month, even confirming a week beforehand. He asked us that when we got to the island, to give him a call and reconfirm this, which I did the first day I got there. The next day, I returned to my hotel to find that Captain Jim had "messed up" with the reservation and double booked another trip. He told us that we could tag along with the other group, which would have been more expensive and not include food, or book with another company. In my opinion, another group came along and booked a trip with him and he screwed us since we were only a group of 2. Don't book with this company unless you are a party of 6 or your reservation might get canceled like ours.
Written July 9, 2007
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
nutmegger08
connecticut2 contributions
after scheduling by email 2 weeks in advance for a 4/29/08 trip, we called jim when we arrived on st thomas on 4/28/08 to confirm. we left a message on his phone and he subsequently left 2 messages at our hotel while we were out to dinner. in the first he confirmed and gave us instructions, but in the second, 2 hours later, he told us he was taking a cruise ship group and apologized for the "mistake." he called again the next morning to try to reschedule us for a later date and to apologize.
we appreciated the apology, but we don't think bumping confirmed passengers at the last minute is ethical business practice. we understand it's a difficult business and that it must be hard to pass up a better offer. on the other hand, we have never experienced this kind of behavior in many years of travelling.
we appreciated the apology, but we don't think bumping confirmed passengers at the last minute is ethical business practice. we understand it's a difficult business and that it must be hard to pass up a better offer. on the other hand, we have never experienced this kind of behavior in many years of travelling.
Written May 1, 2008
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you for you comments. I do sincerely appologize for the scheduling mix up. I did mistakely book both parties for the same day and did not realize it until the day before. Since I had no way to contact the other guests visiting by cruise ship for the day, I hoped I could reschedule you to another day since you were here for the week. I appreciate and value all of my guests reguardless of the size of the party and would never intentionally "bump" any guests.
Capt. Jim
Written March 12, 2012
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Djeremiah
6 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. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Amy C
44 contributions
Oct 2016 • Couples
My husband & I contacted Jim to take us out of a day of sailing during our anniversary trip to St. Thomas. He was prompt & had reasonable prices. He picked us up from Secret Harbor after we enjoyed a delicious breakfast at the location he suggested right in Secret Harbor, Sunset Grille. From first boarding the boat we felt very comfortable with Jim & his two lovely first mates. The boat was gorgeous, very comfortable. We ate lunch aboard that he cooked & it was fantastic! Consisted of chicken, pasta salad, & corn on the cob. The cooler was stocked with beer & sodas. But the real winning drink was Jim's Jester Juice! A mixture of different fresh juices made for a truly one of a kind drink! He will make them virgin as well. We sailed to St. John State Park & snorkeld/swam/floated around for a while before lunch. Then we went to another location, Christmas Cove (I think) to snorkel more. The snorkeling there was awesome! Saw a ray, many pretty fish, and Jim even swam around until he spotted a turtle for us to see! Swimming with the turtle (no touching, of course) was truly magical & my favorite part of our trip. Jim, his boat, & his hospitality really created a beautiful memory for my husband and I to share for many years to come of our first year anniversary trip. If you're thinking about booking a 6 hour day trip aboard this boat, do it!
Written November 1, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hi Amy, it was so great having you both aboard the Legendary Jester Sailing adventures - and we're thrilled you enjoyed the day sailing so much. And thanks for the compliment on our famous :Jester Juice" - we do take pride in our signature drink, that's for sure. Everyone seems to love it - virgin or stout! So very much looking forward to seeing you again next time. Thank you!
Written May 10, 2017
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Dave F
Austin, TX52 contributions
May 2013 • Couples
We just returned from spending 8 the Virgin Islands 8 nights on the fabulous Twilight Rodeo. We would never, ever consider a traditional cruise for a vacation, and this 50' Voyage Catamaran with 4 queen staterooms plus crew quarters, with large indoor and outdoor living areas (with all indoor spaces air conditioned if the fair trades lighten up) provides a sane, comfortable, fun, and affordable alternative. Capt Jim and mate Amanda are great sailors and know the entire US and BVI like the back of their hands, so any itinerary is possible. Very accommodating, both are also excellent cooks and quick with the libations. We were left wanting for nothing the entire trip! The first 4 days of our trip were for business planning purposes, with our entire senior and sales and marketing management teams aboard. What a great way to accomplish serious business while everyone is having a great time in one of the best areas on the planet! Mid way, the work was over, management went home and spouses joined. Now 4 couples, each in their own comfortable, air conditioned stateroom with stereo and private head with shower. Lots of toys like snorkeling gear, paddle boards, kites (even scuba) are on board. And the giant trampolines are a great place while underway, taking a nap, or sleeping under the stars. This great yacht also offers as much shade as anyone may care to enjoy in the abundant VI sunshine! We left the itinerary and meal planning entirely up to Jim and Amanda, and we could not have asked for a better trip. Each destination was outstanding, the trips between each were always at the right time of day and a lot of fun, and they handled going through customs between BVI and ISVI flawlessly. Each beach was better than the one before, every anchorage was beautiful and calm (even the night mother nature threw a squall at us! Jim finished grilling that fresh grouper wearing foul weather gear!) I would very highly recommend chartering Twilight Rodeo with Jim and Amanda. We will be back next year, for sure! We will be packing MUCH lighter, for sure!
Written May 14, 2013
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hey Dave! Thanks so much for the kind words. We are really glad y'all had a good time and enjoyed getting to meet and hang out with all of you. Best to you and Bettina and the rest of the "Beanitos" crew.
J&A
Written July 28, 2013
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
BeckyHouston
Houston, TX21 contributions
Nov 2011 • Couples
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.
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.
Written December 27, 2011
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
bhholley
Kingsport, TN1 contribution
Awesome day, its the best way to kick back and see the beautiful Island scenary. We went swimming and snokeling in some of the beautiful waters. Its just a real relaxing day. The food is great. We had some delicioius marinated grilled chicken, and some great homemade salsa and chips as a snack in the afternoon. It seems like everyone tries to make their version of a 'painkiller', a coconutty pineapple rum drink. But, Jester Juice was the best we had while we were there. Jim and Mo are great hosts, you will really appreciate them if you have ever been on one of the bigger boat trips where they herd you around like cattle and try to keep their schedule.
Written September 8, 2009
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
cperniciaro
Vicksburg, Mississippi
Do you book the boat for overnight trips for multiple days? If not, do you have any recommendations? Thanks!
Written July 2, 2018
Hello. We have sailed with you in the past and had an incredible day. We are planning to visit again on Jan 23, 2019. We are a party of six and will be in town from 7-3pm. What would you suggest and what would be the cost per person please? Thank you. /Deanna
Written May 20, 2018
Rich and Jill are the best! I think their direct email is sailjester.vi a t g m a I l I'm not sure how much each person is but hopefully they can help you out :)
Written August 5, 2018
gdniederst
Cleveland, Ohio
We are a family of 10 and will be cruising to St. Thomas on June 21, 2016. Do you have any private charters for that day? We have a six year old and a four year old with us. Is that a problem?
Written April 3, 2016
Thanks for your interest in Jester Sailing Adventures.
Although I would love the opportunity to take you and your family sailing during your visit to the Virgin Islands, I’m sorry but I do only sail with a maximum of just six guests. There are a few other boats that do sail with larger groups.
Written April 5, 2016
Hi, We tried contacting you over phone and through your website contact form for a booking on May 5 - but unable to get through. Please let me know how I can contact you to make a booking. THanks
Written April 17, 2015
Hi Manish, thanks so much for your interest in Jester Sailing Adventures! I did send an email response and so sorry if you did not receive it. I think you were also trying to book thru the Dive shop Aqua Action. Although I would love to show you and your party a fun and memorable day of sailing and snorkeling, I am already fully booked for Tuesday, May 5th. I did offer some other boats that might still have some availability in my email response.
I hope you can get a your day set up to enjoy our beautiful islands!
Written April 21, 2015
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