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Address: Great Cruz Bay, Cruz Bay 00831, St. John
Phone Number: +1 717-602-3536
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Singing Dog Sailing Catamaran Charters offers luxury USVI & BVI...

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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Best day sailing and snorkeling!

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... read more

5 of 5 starsReviewed 5 days ago
Calgary, Canada

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114 Reviews from our TripAdvisor Community

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  • English first
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English first
Calgary, Canada
2 reviews
5 of 5 stars Reviewed 5 days ago NEW

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
7 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

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
9 reviews
3 attraction reviews
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
Des Moines, Iowa
Level Contributor
7 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed April 24, 2015

We recently spent 3 outstanding days aboard the Off Cay with Captain's Stephen & Kelly. Sailing from St John to Anegada was fantastic highlighted by a open sea Dolphin encounter. We experienced the Island via scooters and dined on lobster and lion fish, before departing for Saba Rock where we spent another wonderful evening. Day 3 we took in the... More 

Thank john k
Berwick, Pennsylvania
2 reviews
5 of 5 stars Reviewed March 21, 2015

We had a trip of a lifetime! Kelly and Stephen are the perfect hosts. The Singing Dog is a beautiful well appointed boat with plenty of places to sit back and relax in the sun. The islands are spectacular, the weather was great, the meals were delicious and the snorkeling was incredible. Saw all kinds of fish and turtles. They... More 

Thank Nancy D

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  • Will you pick up and drop off at my hotel?
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