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Address: Great Cruz Bay, Cruz Bay 00831, St. John
Phone Number: +1 717-602-3536
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Recommended length of visit: More than 3 hours

Singing Dog Sailing Catamaran Charters offers luxury USVI & BVI sailing...

Singing Dog Sailing Catamaran Charters offers luxury USVI & BVI sailing catamaran excursions for private groups departing from St. John & St. Thomas. Superior amenities, attentive service & performance sailing capabilities are features of our charters aboard our spacious 45' (1100 square feet of usable deck and cabin space) luxury sailing catamaran, 'OFF CAY.' So UPGRADE your Coach vacation to First Class with a Singing Dog Sailing catamaran private charter. Let us be your hosts for a memorable day on the water during your next St. John or St. Thomas island vacation. As 'OFF CAY' as you want to be! Singing Dog sailing's luxury catamaran, 'OFF CAY' is stable, comfortable and spacious; you don't have to rub elbows...unless you want to! It's your private yacht for the day! Sailing catamaran 'OFF CAY' ('cause that is where we take you and that is also how the dog sings...) is twice the boat in size compared to mono-hulls of equal length & St John's only first class sailing catamaran offering charters for private groups. Why pay (sometimes more) for an inferior experience? Make your day on the water one you will treasure forever with Singing Dog Sailing where you come as a guest and leave as a friend--without the price-tag you'd expect for a luxury private charter! A NOTE: Trip Advisor members looking for Captain Kelly from St. John--Singing Dog Sailing is the place to find her. So come join the fun and sail with Kelly and the crew of Singing Dog Sailing. Also if you are looking for a reasonably priced mono-hull sailing charter, please consider Salty Dog Day Sails. We are the same company (our sister boat is not new to us, but is a new trip advisor listing, so the rankings are not high YET) with two different boats and levels of service! Try Salty Dog Day Sails for Classic Day sail charters from St. John. (same company, same great service & reputation)!

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TripAdvisor Reviewer Highlights

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The Only Way to Experience the Virgin Islands

I had an amazing time sailing with Kelly and Stephen. The Off Cay was beautiful and clean, the snorkeling sites they took us to were not crowded which led to a really great... read more

5 of 5 starsReviewed 4 weeks ago
Emily M
Hong Kong, China

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116 Reviews from our TripAdvisor Community

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Hong Kong, China
2 reviews
5 of 5 stars Reviewed 4 weeks ago

I had an amazing time sailing with Kelly and Stephen. The Off Cay was beautiful and clean, the snorkeling sites they took us to were not crowded which led to a really great experience, and Kelly and Stephen were wonderful hosts. My favorite experience was swimming with the sea turtles :)

Thank Emily M
Belleville, Kansas
Level Contributor
36 reviews
13 attraction reviews
common_n_attraction_reviews_1bd8 10 helpful votes
5 of 5 stars Reviewed November 29, 2015

A repeat trip with Kelly, Stephen, Admiral Jake and Sailor Sandy was perfect! We arrived to a beautiful table setting of fresh fruit and color coordinated table settings. No paper plates on this cruise! The first mates were unobtrusive yet friendly. We had first time sailors and an 86 year old woman with us. All were put at ease immediately... More 

Thank Nancy H
Calgary, Canada
2 reviews
5 of 5 stars Reviewed November 24, 2015

Wonderful day on Off Cay. Boat is immaculate and Stephan and Kelly are great hosts. I had never been on a big catamaran and it was very cool. Also took us to some great snorkeling. If you are looking for a great sailing experience in the USVI make this the one. Even if you have never snorkeled before, and my... More 

Thank Rickrider1948
Des Moines, Iowa
Level Contributor
9 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed October 14, 2015

We recently made our 4th sail with Singing Dog Sailing and you simply can't beat the experience. The vessel is so pristine clean and the charter so well orchestrated that we already have booked another sail in a few months, they never fail to make a great trip and provide a lot of fun.

Thank john k
Cypress, Texas
1 review
5 of 5 stars Reviewed July 28, 2015

Kelly and Stephen were exceptional! Very outgoing and friendly, knowledgeable of the history of surrounding areas and took us to all of the best places to snorkel!! We enjoyed the entire day from beginning to end!! Would do it again in a heartbeat!! Thanks again Kelly and Stephen!! Ya'll are the best!!

Thank Kelly T
Statesboro, Georgia
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed July 22, 2015 via mobile

We rented a Villa on St. John for a week and went out with Captain's Stephen and Kelly (and Admiral Jake) on their beautiful catamaran for a day. There was six of us in our group and it was the best day of our trip - possibly the best day ever. We knew it was going to be special before... More 

2 Thank Beyondwildestdreams
Level Contributor
11 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 17, 2015

Steve and Kelly are the best! What a way to spend the afternoon with friends to celebrate a special occassion or just for any reason. Jake and Sandy (the two dogs) were so fun and added a feeling of home. This is an ecussion that you should not second guess. Thank you Steve and Kelly for a wonderful afternoon, see... More 

Thank Keith M
Arlington, Virginia
1 review
5 of 5 stars Reviewed June 14, 2015

We booked Captains Stephen and Kelly very late in our trip, and they were easy to communicate and organize with. The day of the trip both the Captains and Admiral Jake were wonderfully friendly, incredibly knowledgeable, and super prepared: the meals and drinks were top notch, the course and destinations were set, and Stephen even snorkeled with us and copied... More 

Thank William H
Glen Allen, Virginia
1 review
5 of 5 stars Reviewed May 21, 2015

Kelly and Stephen, We can't thank you enough for the amazing and memorable experience! We had the best time and really enjoyed meeting you! Thank you for your attention to detail and ensuring we had the best possible experience. Kelly, thanks for taking the time to make sure we were comfortable with the dive. It made all the difference for... More 

Thank hawthornejm
Highlands Ranch, Colorado
Level Contributor
17 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed May 8, 2015

We enjoyed a spectacular day on Off Cay, an impeccably maintained catamaran. Stephen and Kelly make you feel like instant BFFs. They took us to some of the best snorkeling spots in the Caribbean where we saw turtles, rays, and spectacular coral. Unfortunately, my GoPro malfunctioned so I'm unable to share the videos :-( Guess I'll just have to return... More 

Thank Joanie D

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