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Simplicity Charters

Certificate of Excellence
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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 526 reviews
Visitor rating
  • 518
  • 4
    Very good
  • 2
  • 1
  • 0
First Class Outing

Terrific experience with top notch service. My wife and I loved spending the day on the water with the guys. They were friendly, knowledgeable and took great care of us. We had no... read more

Reviewed 5 days ago
Dallas, TX
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526 Reviews from our TripAdvisor Community

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Showing 525: English reviews
Dallas, TX
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
Reviewed 5 days ago NEW

Terrific experience with top notch service. My wife and I loved spending the day on the water with the guys. They were friendly, knowledgeable and took great care of us. We had no issues getting a taxi from the cruise port over to the harbor and they arranged the ride back. Everything ran as smoothly as possible. We got to... More 

Thank Ribbiedog
1 review
Reviewed 1 week ago

I was reviewing photos from our 2015 trip and wanted to thank Captains Charlie and Josh for an amazing day at sea! They took us to some wonderful, secluded spots, and the snorkeling was fantastic. Charlie and Josh (and Hinckley!) were a lot of fun, and the food and drinks were great. It was truly one of the highlights of... More 

Thank Greg F
Little Rock, Arkansas
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 1 week ago via mobile

Simplicity Charters is wonderful! My husband and I can't say enough great things about the the guys and our time on the boat! If you visit St. Thomas, booking a charter with them is a must! This was our second time and it once again did not disappoint. Great sail, snorkeling, drinks and food! Thanks again guys for an amazing... More 

Thank Aaron H
Chicago, Illinois
Level Contributor
22 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 8 helpful votes
Reviewed 2 weeks ago

We booked an all-day sail with Simplicity for May 2nd with another couple coming in on Harmony of the Seas. It ended up being just the four of us on the boat for a peaceful and relaxing day. Charlie and Josh took great care of us, the food was simple but wonderful (BBQ chicken, Spanish rice, Caesar salad), and we... More 

Thank Kevin K
Level Contributor
4 reviews
3 attraction reviews
Reviewed 4 weeks ago

We sailed with Simplicity Charters 5 years ago and knew it was at the top of our list when we returned to St Thomas this spring. Charlie, Josh and Hinckley continue to be great hosts. They have a vast knowledge of the islands and are constantly giving you fun facts. The boat is private (ourselves and one other couple) and... More 

Thank Kristen M
Clarksville, Virginia
Level Contributor
3 reviews
3 attraction reviews
Reviewed 4 weeks ago

Our (Jim, Cindy, and Mona) recent sailing trip with Charlie and Josh was fantastic. We did a fishing trip the day prior and were ready for some relaxation and that is exactly what we got. We just laid back and Charlie and Josh took care of us with their rum drinks and superb lunch. We sailed to some quiet coves... More 

Thank Jim M
1 review
Reviewed 20 April 2017

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 14 helpful votes
Reviewed 17 April 2017

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 Melissa B
1 review
Reviewed 16 April 2017

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 13 April 2017

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

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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?