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Jester Sailing Adventures

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Secret Harbour Beach Resort | (Eastend), 00802, St. Thomas
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Review Highlights
Awesome time sailing with Rich & Jill! Jester is the way to go!

My boyfriend and I were visiting St. Thomas for the week and we wanted to do something on the water... read more

Reviewed 3 weeks ago
Linzee W
Amazing Sunset Sail

If you’re looking for a romantic evening sail this is the most fun boat with the best crew... read more

Reviewed 22 March 2018
Aris G
via mobile
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Overview
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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!
  • Excellent96%
  • Very good2%
  • Average1%
  • Poor0%
  • Terrible1%
Travellers talk about
“captain jim” (222 reviews)
“day sail” (103 reviews)
“corn on the cob” (19 reviews)
Open Now
Hours
Hours Today: 8:00 AM - 8:00 PM
Suggested Duration: More than 3 hours
LOCATION
Secret Harbour Beach Resort | (Eastend), 00802, St. Thomas
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JPMiles / Payback Arrow
50
JPMiles / Payback Arrow
Reviews (528)
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All reviews
"captain jim"
in 222 reviews
"day sail"
in 103 reviews
"corn on the cob"
in 19 reviews
"pasta salad"
in 22 reviews
"highlight of our trip"
in 34 reviews
"great sail"
in 20 reviews
"st john"
in 36 reviews
"laid back"
in 28 reviews
"great lunch"
in 22 reviews
"virgin islands"
in 33 reviews
"great cook"
in 7 reviews
"cruise ship"
in 31 reviews
"secret harbour"
in 10 reviews
"our honeymoon"
in 14 reviews
"fish"
in 32 reviews
"snorkeling spot"
in 7 reviews
"made us feel"
in 15 reviews
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1 - 10 of 526 reviews

Reviewed 3 weeks ago

My boyfriend and I were visiting St. Thomas for the week and we wanted to do something on the water for sure. Jester had great reviews so we decided to check them out. First, I will say they are wonderful communicators! Every time I reached...More

Thank Linzee W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 22 March 2018 via mobile

If you’re looking for a romantic evening sail this is the most fun boat with the best crew. Extremely attentive service in general but the crew (lovely married couple) makes you feel welcome and opens the entire boat to you during the sailing adventure. Sunset...More

Thank Aris G
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
SailJester, Owner at Jester Sailing Adventures, responded to this reviewResponded 24 March 2018

Hi Aris... Indeed it was a special sunset and a special evening. IT was our pleasure having you both aboard and look forward to seeing you next time you find yourself on our little piece of paradise. THANK YOU!

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 16 March 2018 via mobile

We had a great and relaxing time sailing with Rich and Jill, who were very hospitable and knowledgeable hosts. The sailboat was comfortable, the evening breezy and beautiful, and the Jester Juice and snacks were delicious! Definitely worth doing. We had such a good time...More

Thank Barbara R
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
SailJester, Owner at Jester Sailing Adventures, responded to this reviewResponded 24 March 2018

Well hello Barbara - having you and Rick aboard was so much fun. And we are Honored that YOU CAME BACK DAYS LATER... Loved it! We were thrilled you and your friends all enjoyed not only the day of sailing but also truly appreciated the...More

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Reviewed 15 March 2018

Rich and Jill are wonderful people and very accommodating. We took our 4 children (ages 3, 6, 8, 10) on this trip with my parents and had a wonderful day. It was relaxing and enjoyable. The food, atmosphere, and Jester Juice were great! Would HIGHLY...More

Thank pemmama2018
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 15 March 2018 via mobile

My Husband and I along with our kids who are 7 and 9 sailed with Rich and Jill on Jester while on a cruise excursion! The day was amazing! We felt so taken care of! Rich and Jill treated us like family. They were especially...More

Thank Alexa S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
SailJester, Owner at Jester Sailing Adventures, responded to this reviewResponded 24 March 2018

Alexa how special it was that your family joined us for a stupendous day of sailing the Virgin Islands. You have very special kids and family - look forward to next time... THANK YOU

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 2 March 2018

Living on this island, it does rain every once in awhile, tonight was no different, but Capt Jim still took us out even though the other guest cancelled, he still took just myself and my boyfriend out and of course no rain. The seas were...More

Thank Dreamwoman40
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 26 February 2018

Rich and Jill know all the best local spots to see wildlife and incredible views. Definitely, add a sailing excursion to your agenda, you'll be glad you did.

Thank Spencer S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 17 February 2018

We went on a half day sail with Jester Sailing! We wanted to do a full day, but due to the rough waters Capt. Rich advised waiting for calmer seas...which indicated to us that he was interested in our safety and optimum sailing experience! We...More

Thank Shelle89
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 22 January 2018 via mobile

We had the very best time with Rich and Jill going out sailing for a day , not only did we learn so much about the islands , we had a fantastic meal and saw some of the most amazing clear waters !!! A must...More

Thank tschrader64
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 22 December 2017

My wife and I Sail lake Michigan and needed a winter sailing fix. Our day aboard Jester was the perfect answer to Chicago's long winters. Our Captain Rich was friendly and knowledgeable and was a great host. The boat ( Irwin 38 ) is a...More

Thank Jack O
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Questions & Answers
gdniederst
4 April 2016|
AnswerShow all 3 answers
Response from SailJester | Property representative |
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... More
0
Votes
RBB27
18 April 2015|
AnswerShow all 2 answers
Response from SailJester | Property representative |
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... More
0
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