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Simplicity Charters

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Address: 6501 Red Hook Plz | Suite No. 201, Red Hook 00802-1373, St. Thomas
Phone Number:
+1 340-774-9348

For the best day of your vacation in the U.S. Virgin Islands, join us for a...

For the best day of your vacation in the U.S. Virgin Islands, join us for a daysail aboard Simplicity. A beautifully restored 42' Pearson Sloop, Simplicity is sure to impress. Let the crew spoil you and avoid the crowds as we specialize in daysail excursions with no more than six guests. Get a chance to meet "Hinckley," the boats sailing dog that is ususally the star of the show.Sail in the clear tropical waters from St. Thomas to St. John and surrounding cays, while enjoying an open bar, island inspired music, fine food, and an introduction to local Caribbean culture, flora and fauna.

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TripAdvisor Reviewer Highlights

Read all 520 reviews
Visitor rating
  • 512
  • 4
    Very good
  • 2
  • 1
  • 0
Great Day of Sailing on Simplicity

My family and I just spent the best day with Josh and Ray experiencing St. Thomas and St. John on board their beautiful sailboat Simplicity. All I can say is awesome! Ray spent... read more

Reviewed 4 days ago
Mike S
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520 Reviews from our TripAdvisor Community

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Showing 519: English reviews
1 review
Reviewed 4 days ago NEW

My family and I just spent the best day with Josh and Ray experiencing St. Thomas and St. John on board their beautiful sailboat Simplicity. All I can say is awesome! Ray spent time with each of our 3 boys explaining snorkeling. He dove with us and gave us our marine biology lesson. Josh was our skipper and explained everything... More 

Thank Mike S
Baltimore, Maryland
Level Contributor
18 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 12 helpful votes
Reviewed 6 days ago NEW

We were on Allure of the Seas with 6,000 passengers and wanted to get away from the crowds. Wow, was this a great choice. Charlie was awesome to deal with, and patient when we were delayed getting there (the traffic- ugh!). His boat is beautifully maintained, and we enjoyed a lovely sail over to St. John, while Charlie and Josh... More 

Thank MG B
1 review
Reviewed 1 week ago

My wife, 2 boys (ages 11 and 13) and I spent a fantastic day sailing and snorkeling with Charlie, Josh and Hinckley. I was a little concerned with the light morning winds, that my kids would be bored by this experience but Josh and Charlie's passion, energy and hospitality set the tone for an exciting time from the moment we... More 

Thank davidfu2
Des Moines, Iowa
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 1 week ago

Highly recommend this excursion!!! We had a fantastic day with Charlie & Josh as our crew. While Josh snorkeled with us showing us where to look, Charlie fixed a wonderful lunch for us. I will take this charter again if I am in the area.

Thank annie532
St. Thomas
Level Contributor
4 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 3 weeks ago

Truly, the crew and company of our day trip was incredible as well as the ocean beautiful! A definite must plus we will do this again!

Thank tracy a
Orlando, Florida
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 4 weeks ago

Capt Charlie and Josh (and of course Hinckley) are awesome. Our family of four (twin girls age 11) came down to St. Thomas on the Harmony of the Seas. After spending several days aboard the world’s largest cruise ship with 6,000+ people, we needed some time away by ourselves. Simplicity Charters was exactly what we were looking for. We reserved... More 

Thank dpantano
1 review
Reviewed 5 weeks ago via mobile

This day trip sailing excursion is a must do if you're traveling to the St. Thomas/St. John area. From the moment we were picked up in the harbor until the time we were dropped off, Charlie and Josh made it a truly unforgettable experience. Our first stop was in Christmas cove where Josh snorkeled with us and told us all... More 

Thank Andrew A
Level Contributor
3 reviews
Reviewed March 11, 2017

What an amazing day we had. From the minute we showed up till we sadly had to catch a cab back to our ship we were in paradise. Charlie and Josh make you feel like old friends and do everything to make your day perfect. They took us to what amounted to a private reef as we were the only... More 

Thank dsundrud
Gaithersburg, Maryland
1 review
Reviewed March 7, 2017

Our first visit to USVI and we could not have picked a better adventure trip than sailing with Charlie and Josh. Beautiful boat, very knowledgeable crew and the cutest dog "Hinkley". Josh was a great guide with the snorkeling and made me feel very comfortable in the water. Charlie served up a delicious lunch and some excellent rum drinks. I... More 

Thank sdlemmon
Lawrenceburg, IN
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed February 25, 2017 via mobile

This was the second time I was on a trip with Simplicity. As was the last time, the crew was amazing. Drinks served up, great lunchtime meal, sailing was beautiful, and the snorkeling was breathtaking. Definitely recommend and will return again.

Thank drruter

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Questions & Answers

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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?