We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
WINNER WONDERLAND
Win Big When You Book on TripAdvisor

Simplicity Charters

Certificate of Excellence
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
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.

read more

TripAdvisor Reviewer Highlights

Read all 488 reviews
Visitor rating
  • 480
    Excellent
  • 4
    Very good
  • 2
    Average
  • 1
    Poor
  • 0
    Terrible
BOOK IT !!!!

We have multiple friends who have all booked with Simplicity and they all loved it, but cautioned they sell out early, I contacted them about 3 months before our cruise to see if... read more

5 of 5 bubblesReviewed 3 days ago
abctravelers
,
massachusetts
Add Photo Write a Review

488 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
Showing 487: English reviews
massachusetts
Level Contributor
58 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 27 helpful votes
5 of 5 bubbles Reviewed 3 days ago NEW

We have multiple friends who have all booked with Simplicity and they all loved it, but cautioned they sell out early, I contacted them about 3 months before our cruise to see if they had an opening for the 2 of us and we were very happy when the email came that we had a spot! Capt Charlie sent us... More 

Helpful?
Thank abctravelers
Boca Raton, Florida
Level Contributor
208 reviews
29 attraction reviews
common_n_attraction_reviews_1bd8 77 helpful votes
5 of 5 bubbles Reviewed 1 week ago

Every year we take a cruise at Thanksgiving and every year we take one day to charter a boat on one of the islands hoping that it will be the best day of that week - Simplicity certainly made it that for us! Great boat that was very comfortable and nicely maintained and the crew were the best. Charlie and... More 

Helpful?
Thank Hisfriend
Austin, Texas
Level Contributor
7 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 2 weeks ago

This was simply an incredible experience. Josh and Charlie are amazing. My mother had sailed with them a few years prior and it was every bit as fun as she said! We were initially worried about the impending rain, but Josh and Charlie steered us clear of the clouds. They knew about all the surrounding islands and were full of... More 

Helpful?
1 Thank creckart
NJ
2 reviews
5 of 5 bubbles Reviewed 3 weeks ago via mobile

It was terrific!!! Great boat, perfect sunny day, outstanding snorkeling spots, tasty food, boozy drinks and great company! Josh and Ray, it was a pleasure to meet you, guys! Thank you so very much and hope to sail with you again!!!

Helpful?
Thank Lyuba
Lafayette CA
Level Contributor
33 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed 27 July 2016

Incredibly knowledgable and great family boat. These youngish american guys were such fun and tons of info about the islands and history. Just 4 of us on their boat that can actually take 6 people. Boat in super shape and very comfortable. Lunch was homemade BBQ/salad & rice with yummy fruit and treats for dessert. The snorkeling was really a... More 

Helpful?
Thank Cheryl3355
Phoenix, Arizona
Level Contributor
8 reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed 26 July 2016 via mobile

This was one of the most memorable things we have ever done with our teenage children! Beautiful sail and the best snorkeling! Thanks Captain Charlie, Ray and Hinckley!

Helpful?
Thank cjmaggie
1 review
5 of 5 bubbles Reviewed 16 July 2016 via mobile

I've been to many places on vacation me and my wife but nothing has topped this by far went out with Captain Charlie and Joshua and of course first mate Hinckley money well spent time well enjoyed good company good food makes for Good Times must-try if you are in st. Thomas US Virgin Islands no bull must check them... More 

Helpful?
Thank melvincaceres
Port Saint Lucie, Florida, United States
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed 27 June 2016

We took a chance as we booked a last minute Norwegian Escape cruise two weeks ago that was stopping in St Thomas. 6 Years Ago, we sailed with Captain Charlie, 1st Mate Josh and Admiral Hinckley on the Sailing Yacht Simplicity. We had the best time 6 Years Ago and ever since, at least twice a year when we cruise... More 

Helpful?
Thank FoodiePSL
Slippery Rock, Pennsylvania
Level Contributor
1 review
5 of 5 bubbles Reviewed 24 June 2016 via mobile

We decided to venture away from cruise ship tours and take a full say sailing trip on the simplicity. The service you receive from this group is amazing. They only take six people max and that was perfect for our group of three couples. We sailed with Ray and Captain Josh. They took us to two different snorkel , beach... More 

Helpful?
Thank stylinpa
U.S. Virgin Islands
Level Contributor
6 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed 22 June 2016 via mobile

I have to say that this is one of the best sailing trips in the vi. The crew is superb and the boat is beautifully built to handle all seas. This is one day you will never forget. Enjoy the wind in the sails.

Helpful?
Thank Kevin wendy M

Travellers who viewed Simplicity Charters also viewed

 
East End, St. Thomas
St. Thomas, U.S. Virgin Islands
 

Been to Simplicity Charters? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Simplicity Charters and other visitors
12 questions
Ask a question

See all questions (12)

Questions? Get answers from Simplicity Charters staff and past visitors.
Posting guidelines
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?