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“A lifetime experience!”

Jester Sailing Adventures
Certificate of Excellence
More attraction details
Attraction details
Recommended length of visit: More than 3 hours
Owner description: TripAdvisor Certificate of Excellence Winner for 2014, 2015 and 2016! 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!
Useful Information: Activities for young children, Activities for older children, Lockers / storage, Bathroom facilities
New York, New York, United States
Level 1 Contributor
3 reviews
“A lifetime experience!”
Reviewed November 7, 2012

Guess everyone simply loves the sailing trip with Jester, but as a way to express my gratitude for such an experience, my girlfriend forced me to write this review! Our captains are Eric and Jeremy, and we sail with another couple - B.J and Amy. At first I was wondering if a full day trip was too long for me, yes I am not a sailing person, or at least I didn't think so before this trip. But then a full day sailing turns out to be exactly what we are looking for. We snorkeled at two different places, Lovango Cay and another bay that i can't really remember its name.. that happens all the time, because each island here has tons of bays with somehow similar names. We also enjoyed the BBQ chicken and corn cobb, the jester juice and captains' jokes.

Would definitely recommend this experience to any of my friends who would visit VI.

Good luck to you guys, the only disappointment is we missed sea turtle!


Visited November 2012
Thank Joy W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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514 reviews from our community

Visitor rating
Date | Rating
  • Danish first
  • English first
  • French first
  • Any
English first
Valdosta, Georgia
Level 4 Contributor
34 reviews
14 attraction reviews
common_n_attraction_reviews_1bd8 16 helpful votes
“An Amazing Day in the Caribbean! A MUST do!”
Reviewed November 7, 2012

Our travel agent strongly advised we not venture out from their "planned excursions"..so glad we did not listen. I researched activities to do in St. Thomas and came across Day Sails. The reviews were amazing. I was hesitant about spending the money, because we were on a very tight budget for our trip.....but I am so glad we sprung for it. Captain Jim out did himself taking us to all the islands, snorkeling and making an AMAZING lunch aboard the Jester and yes the JESTER JUICE was delicious. My husband and I were celebrating our 10 yr anniversary and honestly I can't think of a better way to celebrate. There is no doubt another trip to St. Thomas and a Day Sail aboard Jester will be in our future. This by far was our fondest memory of our Anniversary cruise. Lastly, getting to the Jester and back to the ship was VERY easy and we had plenty of time to do the whole day sail.

Visited September 2012
Thank mvpage
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Saint Paul, Minnesota
1 review
“Best day in the VI”
Reviewed November 6, 2012

We had a great time on the Jester, We talked them into a special snoorkel spot that was the best of all the VI that we hit on our trip! Jeremy and Eric made it the best time with the stories, drinks, fishing and the great food that was served and the sea turtles were realy cool. The day passed so fast i was wishing for more time on the Jester as the sun whent down.

Visited October 2012
Thank joe m
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Fort Gibson, Oklahoma
Level 3 Contributor
20 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 8 helpful votes
“Best part of our vacation!”
Reviewed November 6, 2012

I found Jester through Trip Advisor and it was a great find. We really enjoyed our day. Our ship landed in St. Thomas, a cab was waiting for us and took us across the island to meet our captain and sailboat. We walked on the beach and got in a small boat to ride out to our catamaran. The day of adventure began! We went to our first Snorkel sight and swam while our crew grilled and cooked us a great lunch of chicken and pasta salad. The corn on the cob with secret ingredients was amazing! Did I forget about the drinks.... with fresh grated nutmeg. After a very relaxing lunch we moved on to our second snorkel sight. We swam with sea turtles, stingrays, and beautiful fish of all kinds. My husband thought he saw Nemo! If we ever make it back we will be looking for the Jester and crew again.

Visited October 2012
Thank TerriC24
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Chicago, Illinois
1 review
“Must do bucket list!”
Reviewed November 1, 2012

Never been sailing before and it was amazing. Went with another couple that did this before so we booked it with them. It is a must do! Glad to say that I did this and would do again! Best part is I was really dark when we returned to the ship! So if you are fair skin wear sunscreen. So glad I went on the cruise and did this! Thanks Captain Jim for the best memories I have for the year 2012! I did this in February of 2012

Visited February 2012
Thank Tammy P
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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