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All 207 St. Thomas Attractions »

Simplicity Charters

6501 Red Hook Plaza | Suite 201, 00802, St. Thomas
340-774-9348
Ranked #3 of 93 tours in St. Thomas
5.0 of 5 stars 141 Reviews
Type: Boat Tours
Owner description: 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,...... more » Owner description: 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. « less
Useful Information: Activities for older children, Activities for young children
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141 reviews from our community

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Date Rating
Crooksville, OH
Senior Reviewer
9 reviews 9 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed 15 May 2012 NEW

My husband and I took this boat trip last Tuesday. Charlie, Ray and Hinkley were great hosts! The weather was great, food fantastic and the snorkeling was amazing. I saw my first eagle ray in Christmas Cove. Very, very good rum punch. We would do this trip again. More

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Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed 12 May 2012 NEW

This was hands down the best part of our week stay in St Thomas. Charley and Josh were so knowledgable about the island and the surrounding islands. They catered this day sail to our specific interests. Hinckley was great company too! Definitely doing it again next time we are in town! More

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NJ
1 review
5 of 5 stars Reviewed 30 April 2012

We couldn't have asked for a better day in St Thomas. Josh went snorkeling with us and pointed out various fish and coral, we would have never known what it was. He was very knowledgeable. Lunch was fabulous! Better then the chicken I had later that night back on the ship!! Both Charlie and Josh gave us a lot of... More

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Toronto, Ontario, Canada
1 review
5 of 5 stars Reviewed 26 April 2012

Charlie, Josh and Hinckley were quite the hosts for our first family sailing excursion. Obviously the destinations were unbelievable, and the sailing relaxing - but these guys really made for a top notch day. I highly recommend them for sailing with chlidren - as they are packed with interesting information about all things V.I, and very helpful in regards to... More

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Pittsburgh
Reviewer
4 reviews 4 reviews
Reviews in 3 cities Reviews in 3 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 24 April 2012

Charlie, Josh, and Hinckley really went above and beyond our expectations! Everything was perfect; the boat, the lunch(bbq chicken better than cruise food) the drinks(tastey rum punch), and the company. They really know what they are doing and we felt safe the entire time. They found the best places to snorkel and hang out. We saw green turtles, a stingray,... More

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Jacksonville
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 21 April 2012

We just returned from a 1-week stay in St. Thomas.My husband booked a private full-day sail for us on our first vacation day. Charlie and Josh are experienced captains and amazing hosts. The waters were rougher than usual and I got sea sick. They were so accommodating. They quickly adjusted plans to allow us more time on a secluded beach... More

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Clearwater, Florida
Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed 2 April 2012

We booked this private sail and snorkel trip through the reviews here on Trip Advisor about one week out of our Cruise on Celebrity Summit. Let me tell you there is no disappointment here. Charlie, Josh and Hinckley are true masters at sailing the Islands. You will get a sense of comfort with them. Avoid the cattle call runs with... More

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Saint James, New York
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed 28 March 2012

We were in St. Thomas for the day on a cruise ship and booked a full day sail. Charlie, Josh and Hinckley were amazing hosts. We had a day of wonderfully peaceful snorkeling, sailing and a great BBQ lunch. We will definitely go out with them again next year! More

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Chicago
Senior Reviewer
8 reviews 8 reviews
Reviews in 5 cities Reviews in 5 cities
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 26 March 2012

Charlie and Josh were the perfect sailors for this adventure. They gave us an amazing tour and fed us very well. It made us want to move to st. Thomas permanently and was the highlight of our trip. More

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Waterford, WI
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 19 March 2012

My fiancée and I booked this charter with our friends who were celebrating their tenth wedding anniversary. We looked forward to our day on Simplicity and they did not disappoint. The weather was beautiful. The boat was was gorgeous. The guys were super friendly. Hinkley stole the day, a real charmer. Ray and Josh are very knowledgeable and love their... More

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