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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
Website
Description:

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 514 reviews
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Experience of a Lifetime

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... read more

5 of 5 bubblesReviewed 6 days ago
Andrew A
via mobile
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514 Reviews from our TripAdvisor Community

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Showing 513: English reviews
1 review
5 of 5 bubbles Reviewed 6 days ago NEW 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 

Helpful?
Thank Andrew A
Napa
Level Contributor
3 reviews
5 of 5 bubbles Reviewed 2 weeks ago

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 

Helpful?
Thank dsundrud
Gaithersburg, Maryland
1 review
5 of 5 bubbles Reviewed 2 weeks ago

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 

Helpful?
Thank sdlemmon
Lawrenceburg, IN
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 4 weeks ago 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.

Helpful?
Thank drruter
2 reviews
5 of 5 bubbles Reviewed 10 February 2017 via mobile

Charlie and Josh-- you guys make our vacation. The two of you make us feel like we are special, but I know you guys treat everyone special. We've gone on the Simplicity for probably 6 years always, always great. Hinckley we love you and hope you will be there for our sail.. next time. Jiggs Deb Dorinda Mike

Helpful?
Thank Debra W
Nashville, Tennessee
Level Contributor
13 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 6 February 2017 via mobile

My wife and I have day sailed USVI many times over the last 10 years with a number of different crews. Captain Charlie and Josh (also certified captain) have been sailing since they were 5 years old and they navigated their 42 ft sloop like pros. Josh (degree in marine biology) then gave our small group a personalized and most... More 

Helpful?
Thank jevhmedcon
Houston, Texas
Level Contributor
4 reviews
5 of 5 bubbles Reviewed 31 January 2017

Charlie, Josh and Admiral Hinckley were amazing hosts for our lunch time sail and snorkel trip. They took us to Christmas Cove for some spectacular snorkeling, and they gave us a thorough historical tour around the islands on the way there and back. The lunch that Charlie prepared was delicious, and they kept the rum punch flowing the entire trip... More 

Helpful?
Thank Dave M
Level Contributor
1 review
5 of 5 bubbles Reviewed 27 January 2017

We love the crew for this boat, and we love the fact that it's a small group. The lunch they prepare is delicious, and we enjoyed the snorkeling and island stops we made. Hinckley is a great dog that seems to love boat life, yet she's afraid of the water. The crew is friendly, and they are very knowledgeable about... More 

Helpful?
Thank Raye H
Medford, New Jersey
Level Contributor
18 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 14 helpful votes
5 of 5 bubbles Reviewed 25 January 2017

Charlie, Josh and Admiral Hinckley ( their 10 yr old rescue dog) treated us to the very best sailing day possible. Captains Charlie and Josh took us to amazing private areas to snorkel or just float around with a noodle. Drinks were flowing all day long and Charlie is an amazing cook , serving delicious freshly made grilled chicken, right... More 

Helpful?
Thank uvalax
Winnipeg, Canada
Level Contributor
8 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed 24 January 2017 via mobile

Visited Jan-16 for our cruise stop. The place was easy to find, taxi was flat fee per person and Charlie arranged a taxi for us when we got back. It was a windy day, no doubt about that, but that made the sailing special. I was worried for our snorkeling as water was rough and wind was blowing, BUT, Charlie... More 

Helpful?
Thank yycish

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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?