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Jester Sailing Adventures

Certificate of Excellence
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Address: Secret Harbour Beach Resort, 00802, St. Thomas
Phone Number: +1 340-513-2459
Website
Description:

2014 Certificate of Excellence Winner! Fun-filled daysail adventures to St....

2014 Certificate of Excellence Winner! 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 Capt'n Jim's freshly prepared gourmet grub and luscious specialty libations! Convieniently located on the East End of St. Thomas near most resorts and an easy ride from the cruise ship dock. Sail Jester and experience the very best of the Virgins!

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TripAdvisor Reviewer Highlights

Read all 460 reviews
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Pure relaxation and fun with Captain Jim!

We had heard from friends that Captain Jim was amazing and well worth the investment. We had missed him our last trip to St. Thomas but booked him this time...and it was... read more

5 of 5 bubblesReviewed 2 days ago
sdceaburton
,
Newport, Rhode Island

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460 Reviews from our TripAdvisor Community

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Showing 458: English reviews
Newport, Rhode Island
1 review
5 of 5 bubbles Reviewed 2 days ago NEW

We had heard from friends that Captain Jim was amazing and well worth the investment. We had missed him our last trip to St. Thomas but booked him this time...and it was phenomenal! My wife and I luckily had the boat to ourselves and thoroughly enjoyed the sailing, snorkeling, Jester Juice and great barbeque! Can't wait for our next trip!

Helpful?
Thank sdceaburton
Nashville, Tennessee
Level Contributor
5 reviews
5 of 5 bubbles Reviewed 2 days ago NEW via mobile

Girlfriend and I took a half day trip with Capt Jim. It was by far the best charter trip I have ever been on. We had some great snacks and beverages. The place we stopped to go snorkeling was incredible! Saw some rays, great coral reef and beautiful fish. Don't waste your time looking for other trips. This is exactly... More 

Helpful?
Thank langleyandtaylor
2 reviews
5 of 5 bubbles Reviewed 4 days ago NEW via mobile

Together with family visiting, we went out for a day sail with Captain Jim and mate Deb. Nothing but relaxing, fun and sailing. We had wind and were cruising alone beautifully. Had yummy lunch and lots of Jester Juice. Be sure to try it! My family said better than pain killers!!! You won't go wrong by sailing on Jester. Can't... More 

Helpful?
Thank lynda m
Byron, Georgia
Level Contributor
9 reviews
common_n_attraction_reviews_1bd8 10 helpful votes
5 of 5 bubbles Reviewed 4 days ago NEW via mobile

We had such a great time sailing with Capt Jim! We can't wait to go back and go on an all day sail around the island. Good and drinks were fantastic and the boat is beautiful and well maintained. Thanks Capt Jim. See next year!!!

Helpful?
Thank keith W
Salt Lake City, Utah
Level Contributor
3 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed 6 days ago NEW

This was an amazing experience that I hope we can do again very soon! Jim was the best Captain I have every sailed with and Deb was amazing! They created a relaxed environment and hospitality that make this one of the best experiences we had while in the Virgin Islands. Highly recommended!!

Helpful?
1 Thank Russ C
SailJester, Owner at Jester Sailing Adventures, responded to this review

Hey Russ, Thanks so much!! I was a pleasure sailing with you, Summer, Sam and Emily!! It truly was an epically "Worthy" adventure!! Start planning your next visit soon!! Capt. Jim More 

2 reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed 1 week ago via mobile

As a Saint Thomas local I can strongly say this has been my best experience on island thus far. We had family in town (7 of us) and he fit us in for a full day sail no problem. He had all the drinks we needed.. all the gear we needed and absolutely all the food we needed (and it... More 

Helpful?
1 Thank Sierra G
SailJester, Owner at Jester Sailing Adventures, responded to this review

Hey Sierra, Thanks so much!! It was great having you and your family aboard! Its so great when family gets to experience the beauty and awesomeness islands!! Capt. Jim More 

Sandy, Utah
Level Contributor
9 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 20 helpful votes
5 of 5 bubbles Reviewed 2 weeks ago via mobile

Our trip on the Jester was absolutely "WORTHY"!!! We spent the day sailing, partaking of Jester's juice and laughing all day long. There was ample relaxation and good vibes. Jim and Deb went above and beyond to not only be hospitable, but also had fun with us. The lack of wind was "brutal"....but not for Cpt. Jim! Captain Jim will... More 

Helpful?
1 Thank Wimskee
SailJester, Owner at Jester Sailing Adventures, responded to this review

Thanks Sam!!! it was great to sail with you Emily and the Cottam's. Im so glad you all got to experience the islands just like a Kenny song!! Capt. Jim More 

Huntsville, Alabama
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed 4 weeks ago

A perfect day. Didn't have to worry about a thing. Captain Jim took care of everything and had plenty of gear. Fun time and would highly recommend.

Review collected in partnership with this attraction

Helpful?
1 Thank darcie_ziert
Level Contributor
12 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed 1 November 2016 via mobile

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... More 

Helpful?
3 Thank Amy D
St. John
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 25 October 2016

I am a local Lifestyle Wedding Photographer and I got to finally meet and work with Captain Jim this summer. He was sweet as pie, a wonderful host and doubled as an officiant ready to conduct a beautiful afternoon sail boat wedding ceremony!

Helpful?
Thank SavanahLoftus

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?