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Singing Dog Sailing Day Tours

Certificate of Excellence
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Address: Great Cruz Bay, Cruz Bay 00831, St. John
Phone Number:
+1 717-602-3536
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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Absolute the best

Sailing with Kelly and Stephen is the very best. You will not be disappointed unless you wait too long to book the trip.

5 of 5 bubblesReviewed 4 weeks ago
St. John

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130 Reviews from our TripAdvisor Community

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Showing 130: English reviews
St. John
Level Contributor
46 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 11 helpful votes
5 of 5 bubbles Reviewed 4 weeks ago

Sailing with Kelly and Stephen is the very best. You will not be disappointed unless you wait too long to book the trip.

Thank monica417
SingingDogSailing, General Manager at Singing Dog Sailing Day Tours, responded to this review

Thank you do the feedback, Monica! We were glad we were able to host your group for a sailing excursion. What an incredible day on the water! Looking forward to future fun. More 

Hugoton, Kansas
Level Contributor
5 reviews
5 of 5 bubbles Reviewed January 6, 2017

Been to the Virgin Islands several times and we book with Singing Dog Sailing every time. The owners are great people that cater to the trip you want to take. This is always the first thing we book anytime we know we are coming to the islands.

Thank trindels23
SingingDogSailing, Manager at Singing Dog Sailing Day Tours, responded to this review

Thank you for your review and thank you for choosing Singing Dog Sailing for several sailing trips each year you visit. We enjoy seeing the family and watching the kids grow. We literally were just comparing photos of trips over the years. What fun. What great sailing. What great memories! Looking forward to hosting you next year. More 

Owls Head, Maine
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed December 15, 2016

I can't recommend Kelly & Stephen of Singing Dog Sailing enough!!! I've sailed with them three separate times with family while on vacation in St. John, and the trip has exceeded our expectations every single time. Not only are they incredibly friendly (they feel like family now), the boat is gorgeous (and so much bigger than we expected the first... More 

1 Thank Mackenzie M
SingingDogSailing, Manager at Singing Dog Sailing Day Tours, responded to this review

Mackenzie we thank you for the glowing feedback and the great memories of fun family sailing trips. We look forward to having you visit in the Virgin Islands for more fun on the water. Thanks for supporting Singing Dog Sailing More 

Des Moines, Iowa
Level Contributor
16 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed November 28, 2016

We always book Singing Dog Sailing when we are in the Caribbean however if you ever get the chance to sail Martha's Vineyard with Captains Stephen & Kelly you will be in for a fantastic time. They always make certain to maximize your experience and the vessel is always sparkling clean. Fun Fun Fun.

Thank john k
SingingDogSailing, Manager at Singing Dog Sailing Day Tours, responded to this review

We love that our charter guests are so loyal and committed to Singing Fog Sailng that they are will g to plan their vacations around the boat location. What fun memories of sailing in New England and Marthas Vineyard. Thanks for following and supporting us and we look forward to seeing you again in the USVI. More 

Kansas City, Kansas
2 reviews
5 of 5 bubbles Reviewed November 23, 2016

Sailed with Kelly, Stephen,Jake and Sandy on their magnificent sailing cat Off Cay,and had just about the best day a sailing junkie and avowed St. John addict can have from the easy friendly booking and planning through the coffee and fresh baked rolls to the raising of sails and feeling that warm breeze on your face. A personal snorkeling guide... More 

Thank 8274xray
SingingDogSailing, Manager at Singing Dog Sailing Day Tours, responded to this review

Doc, you and the family are welcome anytime. We are grateful that you choose Singing Dog Sailing each St John vacation. What memorable sailing adventures with great guests. Thanks for supporting us and spreading the word about the best St John sailing option! More 

Saint Augustine Beach, Florida
1 review
5 of 5 bubbles Reviewed November 10, 2016

I was lucky enough to meet up with Kelly and Steven in Gloucester, MA and go for a great sunset sail through the harbor. Beautiful boat, well kept and very comfortable under sail with lots of awesome places to lounge while enjoying the view. Complete with a great dingy for transport to and from shore. Both are gracious, fun hosts... More 

Thank _jen32084
SingingDogSailing, Manager at Singing Dog Sailing Day Tours, responded to this review

Thank you for your review and for sailing with us while we were in New England chartering this past summer. We hope to have the pleasure of hosting you in the USVI on an upcoming vacation. More 

1 review
5 of 5 bubbles Reviewed October 29, 2016 via mobile

Could not think of a better way to spend a day on St. John, Singing Dog Sailing knows the best snorkeling spots, beach bars and views to make sure every day you spend with them is beyond incredible. It helps that their captains are a truly enjoyable addition to your day trip!

Thank Virginia S
1 review
5 of 5 bubbles Reviewed October 19, 2016 via mobile

What an amazing trip! Can't wait to go again. Food, hosts and sail was beyond the highest of expectations

Thank jendouglass
Leucadia, California
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed October 18, 2016 via mobile

The boat was super clean, the crew was so fun! And the captain (Sandy the Dog) was amazing!!! I didn't want to come home. They took care of my 93yr old grandma & family as if we were one of their own. I can't wait to go back!!!. Words can't express how sweet this family vacation was thanks to the... More 

Thank SweetMauiMelissa
Glen Ellyn, Illinois
Level Contributor
4 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed May 17, 2016 via mobile

Loved our time sailing with Stephen and Kelly. The trip was a perfect way to spend with friends enjoying the sun and the sea. Already looking forward to our next opportunity to sail with Singing Dog Sailing.

2 Thank jeanGEIL

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