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Simplicity Charters

6501 Red Hook Plz | Suite No. 201, Red Hook 00802-1373, St. Thomas
+1 340-774-9348
Review Highlights
Simply The Best! Like sailing with good friends!

To steal a term of Captain Charlie, Avoid the "Cattlemaran" tours and treat yourself to the best... read more

Reviewed 1 week ago
Susan C
via mobile
Great snorkel trip

Really enjoyed our morning with Charlie and ray. Top notch service and just all around nice guys... read more

Reviewed 3 weeks ago
Dyer, IN
via mobile
Read all 530 reviews
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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.
  • Excellent97%
  • Very good1%
  • Average1%
  • Poor1%
  • Terrible0%
Travelers talk about
“rice” (31 reviews)
6501 Red Hook Plz | Suite No. 201, Red Hook 00802-1373, St. Thomas
+1 340-774-9348
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Reviews (530)
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1 - 10 of 528 reviews

Reviewed 1 week ago via mobile

To steal a term of Captain Charlie, Avoid the "Cattlemaran" tours and treat yourself to the best way to see the islands above and below the waterline. This was our second sail with Simplicity and once again they stepped up and delivered. Charlie and Ray...More

Thank Susan C
Reviewed 3 weeks ago via mobile

Really enjoyed our morning with Charlie and ray. Top notch service and just all around nice guys. Took us to Christmas cove for perfect snorkeling. I would highly recommend!!

Thank Twinsmom99
Reviewed 5 weeks ago

Thank you Ray and Joshua for an amazing day on the water. We enjoyed the snorkels, sailing & history. Lunch looked great (my husband enjoyed it.. remember I couldn't eat). ; ) We appreciated that Simplicity keeps the excursions to a small group. It makes...More

Thank msfcambridge
Reviewed May 22, 2017

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...More

Thank Ribbiedog
Reviewed May 19, 2017

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,...More

Thank Greg F
Reviewed May 15, 2017 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...More

Thank Aaron H
Reviewed May 11, 2017

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...More

Thank Kevin K
Reviewed April 28, 2017

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...More

Thank Kristen M
Reviewed April 24, 2017

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...More

Thank Jim M
Reviewed April 19, 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...More

Thank Mike S
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Questions & Answers
March 29, 2017|
AnswerShow all 2 answers
Response from SimplicityCharters | Property representative |
I am available for a full day sail on May 17th, 2017. Our full day sail is six hours and we could sail from 9:15AM-3:30PM local Atlantic Standard Time. We are a small company and only take a maximum of six guests. You will... More
March 1, 2016|
Response from SimplicityCharters | Property representative |
Our boarding ladder goes three steps into the water. Although I will say it is basically her vertical so some find it harder than others. We dour best to offer help and try to make it as easy as possible.
January 20, 2016|
Response from NYCfamily10065 | Reviewed this property |
they will do a full or half day sail