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Jester Sailing Adventures

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Secret Harbour Beach Resort | (Eastend), 00802, St. Thomas
+1 340-513-2459
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Review Highlights
AMAZING!

We went on a half day sail with Jester Sailing! We wanted to do a full day, but due to the rough... read more

Reviewed 1 week ago
Shelle89
,
Dougherty, Iowa
A must do on vacation

We had the very best time with Rich and Jill going out sailing for a day , not only did we learn so... read more

Reviewed 4 weeks ago
tschrader64
,
Prior Lake, Minnesota
via mobile
Read all 522 reviews
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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” (223 reviews)
“day sail” (101 reviews)
“corn on the cob” (19 reviews)
Open Now
All hours
Hours Today: 8:00 a.m. - 8:00 p.m.
Suggested Duration: More than 3 hours
LOCATION
Secret Harbour Beach Resort | (Eastend), 00802, St. Thomas
CONTACT
Website
+1 340-513-2459

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Write a ReviewReviews (522)
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"captain jim"
in 223 reviews
"day sail"
in 101 reviews
"corn on the cob"
in 19 reviews
"pasta salad"
in 22 reviews
"highlight of our trip"
in 34 reviews
"delicious lunch"
in 26 reviews
"st john"
in 36 reviews
"laid back"
in 28 reviews
"virgin islands"
in 33 reviews
"great cook"
in 7 reviews
"beautiful sail"
in 7 reviews
"secret harbour"
in 10 reviews
"our honeymoon"
in 14 reviews
"snorkeling spot"
in 7 reviews
"fish"
in 30 reviews
"great captain"
in 12 reviews
"made us feel"
in 15 reviews
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1 - 10 of 520 reviews

Reviewed 1 week ago

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 4 weeks ago 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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Reviewed 26 November 2017 via mobile

Had an amazing time out on the Jester boat. What a great couple (captain Rich and first mate Jill) were so warm and accommodating making the day so memorable. The "Jester Juice" was fantastic. I highly recommend you contact them when in the USVI.More

Thank Cujonole
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 27 November 2017

How sweet - you know you're making us blush with your very kind words, right?!! We had a blast taking you guys out sailing and are so much looking forward to doing again when you find yourself back on our little piece of paradise. Thank...More

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 27 October 2017

We sailed Jester in late August 2017. It was an awesome day! Would definitely book Jester again, when we return. Small group of people, customized cruise. We were pampered in style! The day felt like we were out sailing with long time friends! They took...More

Thank Julien C
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 27 November 2017

Pampering our cherished guests while sailing the sapphire waters is f the Caribbean is what we do best! Thank you for your awesome words.

Report response as inappropriate
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Reviewed 26 October 2017

My sister, brother in law, husband, and I were on St. Thomas for less than a day (cruising). We weren't interested in shopping, so our group of four went on a snorkel cruise to St. John. It was so wonderful and relaxing. We saw so...More

Thank CruiseDirectorAmy
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 2 December 2017

Hi Amy, thank you SO much for your kind words... it was a blessing having you and your crew on-board The Jester - sure would love to see you again here in paradise again soon. Thank you again!

Report response as inappropriate
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Reviewed 2 October 2017 via mobile

We had used Jesters before on another cruise so we knew that we were going to have a great time. My wife and kids (11 and 8) and our neighbors and their kids (same ages) booked a full day sail. Took a short ride from...More

Thank lawdog1674
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 27 November 2017

We are truly honoured you chose Jester Sailing Adventures for your island excursion - hope to see you again when you guys are next in the Virgin Islands. Thank you again..!

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 28 August 2017 via mobile

Excellent attention of the crew and Captain Jim , the trip was amazing. Have a good snorkeling experience at chritsmas cove island and sunset view!!! Definitely recommended it !!!

Thank Hectornt1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 24 July 2017

This is such a great experience that we do it every year. Great snorkeling, Awesome Jester Juice and relaxing on the front deck rocked by waves. A great time with Captain Jim and friends.

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Thank juditherb
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 18 July 2017

Single dad who took my boys, 6 and 9, for a special week in St. Thomas. Found Jester adventures and couldn't have asked for a better experience. The captain and the crew was fantastic and treated us like family. Very interactive and was outstanding to...More

Thank Jackson's P
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Ask a question
Questions & Answers
gdniederst
3 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
17 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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