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Jester Sailing Adventures

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Opens in 18 min: 8:00 AM - 8:00 PM
Open today: 8:00 AM - 8:00 PM

Jester Sailing Adventures
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Certificate of Excellence
Traveler Overview
  • Excellent96%
  • Very good2%
  • Average1%
  • Poor0%
  • Terrible1%
Travelers talk about
“captain jim”(222 reviews)
“day sail”(107 reviews)
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...more
Opens in 18 min
Hours Today: 8:00 AM - 8:00 PM
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Suggested duration: More than 3 hours
Secret Harbour Beach Resort | (Eastend), 00802, St. Thomas
+1 340-513-2459
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Reviews (551)
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All reviews captain jim day sail highlight of our trip great sail st john great lunch taxi driver cruise ship great hosts fish took great care visiting st vacation thomas cove mate helm
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1 - 10 of 549 reviews
Reviewed yesterday via mobile

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....More

Date of experience: December 2018
Thank Rainmom88
Reviewed yesterday

My wife and I were on a cruise just after X-Mas and were able to book an all day sail with Jester. We typically book with the local tour operators directly, you get a better tour, better selection and these folks are professional and will...More

Date of experience: January 2019
Thank Dan O
Reviewed yesterday

I don't usually leave reviews, but I told myself that I would after a great time. I went on a cruise over Christmas week and it had a stop in st Thomas on Christmas day. My family has never been to the Caribbean and they...More

Date of experience: December 2018
Thank Stephiin
Reviewed yesterday

We had an awesome 1/2 day sailing with Rich and crew in January while on a cruise. Rich is experienced and a pleasure to be with. Wish we had booked a full day of sailing with him to see other islands. The cove where he...More

Date of experience: January 2019
Thank samloua8
Reviewed yesterday via mobile

my Girlfriend and I had a great day sailing with Jester and crew. They served a great lunch and the whole trip was just relaxing and adventurous. This was a highlight of our vacation and a great.value for the money. Thanks again for the taxi...More

Date of experience: February 2019
Thank David W
Reviewed 3 days ago

We spent the day with Captain Rich, Jill, and Brian on an all day sail. We had an amazing day sailing and snorkeling. Lunch was amazing, and the service was above excellent. The attention to detail was exceptional. We started the day as strangers, and...More

Date of experience: February 2019
3  Thank Denise757Sail
RichS722, Owner at Jester Sailing Adventures, responded to this reviewResponded yesterday

Oh My Gosh... Your mention of feeling Like Family is So flattering because that is what we always want form our guests and you sure do have a WONDERFUL Family. What an stupendous time we had with you guys. Can't wait for the next time!...More

Reviewed 6 days ago via mobile

Awesome experience! Highly recommend! Captain Rich and Captain Jill are awesome hosts! Beautiful boat. The Jester juice with fresh nutmeg will make you relax and melt your worries away. We did the sunset sail which was fantastic but look forward to going back for a...More

Date of experience: February 2019
2  Thank dschultz2016
RichS722, Owner at Jester Sailing Adventures, responded to this reviewResponded 3 days ago

What a wonderful review guys... you're making us blush ya know (LOL) You two are such a fantastic couple, we truly can not wait for you to return... we'll save you a seat on Jester and of course the Jester Juice will be a'flowin! OH...More

Reviewed 3 weeks ago

Timely communication and flawless coordination. Our party of two was paired with a party of three for a half day sail and snorkel. We met up at the easy to reach Secret Harbor. Excellent weather for sailing and everyone having fun. With the Jester at...More

Date of experience: January 2019
2  Thank Teri H
RichS722, Owner at Jester Sailing Adventures, responded to this reviewResponded yesterday

Hi again Teri. Indeed it was a perfect day on the water, right? And what fun we had... it was simply Fantastic. Also so glad you enjoyed the fresh lunch and bottomless beverages. Sooo looking forward to hosting you onboard again. Thank you again Rich...More

Reviewed 4 weeks ago

We have been out on the Jester a couple times before. This trip was the very best. We took a friend for her birthday. Rich and Jill were great hosts, the wind really cooperated and gave us a great day of sailing. We snorkeled off...More

Date of experience: January 2019
2  Thank Phyllis143
RichS722, Owner at Jester Sailing Adventures, responded to this reviewResponded yesterday

Hi Phyllis. What a great time we had with you guys coming back on-board for a truly fun-filled day on the Caribbean Sea. Very much looking forward to seeing you next time. Thank you again!

Reviewed December 17, 2018

My wife had been on the Jester Jim about 15 years ago and had an amazing experience. So we contacted and received confirmation emails for our reservation on 12/15/18. This was the last port of our 10 day cruise. We took the taxi ($20.00 fare...More

Date of experience: December 2018
2  Thank Dave J
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Questions & Answers
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May 19, 2018|
Response from Spencer S | Reviewed this property |
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 :)
April 3, 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