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.
Win Big When You Book on TripAdvisor

Singing Dog Sailing Day Tours

Certificate of Excellence
Sponsored by:
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Sponsored by:
Get directions
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)!

read more

TripAdvisor Reviewer Highlights

Read all 127 reviews
Visitor rating
  • 127
  • 0
    Very good
  • 0
  • 0
  • 0
New adventure

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... read more

5 of 5 bubblesReviewed 1 week ago
john k
Des Moines, Iowa

Similar Things to Do in Cruz Bay

Add Photo Write a Review

127 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Showing 127: English reviews
Des Moines, Iowa
Level Contributor
16 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed 1 week ago

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
Kansas City, Kansas
2 reviews
5 of 5 bubbles Reviewed 2 weeks ago

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
Saint Augustine Beach, Florida
1 review
5 of 5 bubbles Reviewed 4 weeks ago

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
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
1 review
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
Fort Lauderdale, Florida
Level Contributor
28 reviews
11 attraction reviews
common_n_attraction_reviews_1bd8 21 helpful votes
5 of 5 bubbles Reviewed March 29, 2016

Captain Kelly, Captain Stephen and their singing dog Admiral Jake made us feel so welcome, like we were guests in their beautiful catamaran home. We really appreciated the excellent snorkel equipment they had for the six adults and four kids in our group - the best masks and flippers I have ever used. They took us to a wonderful snorkel... More 

5 Thank Shoshanna E
Rochester, New York
Level Contributor
10 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed March 14, 2016

I have had the pleasure of spending a few different occasions out on the water with Captain's Kelly and Stephen. They are top notch. The vessels are spotless and gorgeous. You will have an amazing day on the water with them and their crew. Their knowledge of the waters above and below are unmatched. Captain Stephen jumps right in and... More 

Thank Barb Y
SingingDogSailing, Owner at Singing Dog Sailing Day Tours, responded to this review

Thank you so very much for taking time to review Singing Dog Sailing, Barb. We enjoyed hosting such a fun group of friends and look forward to your annual trips. May all your sailing dreams come true until next time. Your Captains. More 

Charlotte Amalie, St. Thomas
Level Contributor
5 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed March 12, 2016

We have sailed with Kelly and Stephen 4 times now, and every time has been wonderful! We have sailed to the BVI's, and we have also stayed in the USVI's. Whatever we do and wherever we go, the hospitality is the best, food delicious, drinks plentiful and snorkeling spectacular. Off Cay is quite beautiful and we always feel spoiled. Highly... More 

1 Thank Mary J

Travelers who viewed Singing Dog Sailing Day Tours also viewed

St. John, U.S. Virgin Islands

Been to Singing Dog Sailing Day Tours? 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 Singing Dog Sailing Day Tours and other visitors
1 question
Ask a question
Charleston, South Carolina

See all questions (1)

Questions? Get answers from Singing Dog Sailing Day Tours 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?