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Singing Dog Sailing

Features Animals
Cruz Bay 00831, St. John
+1 340-244-8230
Review Highlights
Amazing Experience with Singing Dog Sailing!

I was lucky enough to spend a day aboard Offcay for my Bachelorette party. Kelly and Stephen were... read more

Reviewed May 14, 2017
Emily W
via mobile
Best Day In the Islands

We have had the opportunity to sail with Kelly and Stephen many times over the years. It is the... read more

Reviewed May 10, 2017
Oxford, Connecticut
Read all 148 reviews
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Singing Dog Sailing Catamaran Charters offers luxury USVI & BVI sailing catamaran excursions for private groups of up to 12 passengers 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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Travelers talk about
“admiral jake” (23 reviews)
Suggested Duration: More than 3 hours
Cruz Bay 00831, St. John
+1 340-244-8230
Write a ReviewReviews (148)
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11 - 20 of 148 reviews

Reviewed May 14, 2017 via mobile

I was lucky enough to spend a day aboard Offcay for my Bachelorette party. Kelly and Stephen were the best hosts, providing delicious food and painkillers, showing us some of the best snorkeling I've seen in the Caribbean, and ensuring we had a blast on...More

Thank Emily W
Reviewed May 10, 2017

We have had the opportunity to sail with Kelly and Stephen many times over the years. It is the highlight of our trip, they are amazing hosts, the boats are immaculate and you always feel safe and at ease with them. Everything is taken care...More

Thank Stephen1213
A TripAdvisor Member
Reviewed April 24, 2017

We went out for the day to Soggy Dollar Bar and snorkeling on Honeymoon beach. Justin and Pepper were Great!! What a wonderful day! The highlight of our trip!!

Thank A TripAdvisor Member
Reviewed April 20, 2017 via mobile

Our day with Kelly and Steve was the highlight of our trip! They are wonderful hosts and very knowledgeable about the islands. The snorkeling was awesome and lunch on the boat was great as well. Would highly recommend!!!!!

Thank bjh851
Reviewed April 10, 2017

Kelly and Steve, who host the trip are really professional, fun people. They were really dedicated to making sure our family of 9 had a really great trip that exceeded expectations. We did the full-day USVI trip and are definitely interested in doing the full-day...More

Thank Taha S
Reviewed April 2, 2017 via mobile

You will never go wrong with Singing Dog Sailing as your host. This is our third trip with them and it was a terrific trip from start to finish. We sailed the Salty Dog on this day and our Captain Justin and first mate Pepper...More

Thank Judy C
Reviewed March 19, 2017

We loved our trip on this beautiful 37 foot catamaran! Justin Holt was our captain and we enjoyed every minute on board this beautiful, immaculately clean ship! We sailed over to Christmas Cove in Saint Thomas to watch sea turtles swimming around us! We swam...More

Thank easbeal1955
Reviewed March 3, 2017

This was our 6th trip with Kelly and Stephen aboard beautiful Off Cay. We brought our adult children and their two friends. As usual, we were greeted warmly and right on time, and a lovely fruit tray with fresh baked pastries awaited us, along with...More

Thank Mary J
Reviewed February 26, 2017 via mobile

My third time sailing and by far my favorite. 7 other people and I went on the trip. We were on little dog a 37 foot catamaran. I had a great time, we went to Christmas cove near St Thomas and went snorkeling. I saw...More

Thank river_rat_felix
SingingDogSailing, Owner at Singing Dog Sailing, responded to this reviewResponded February 28, 2017

What great feedback about your day! Thank you for choosing a day sail with Singing Dog Sailing. We hope to have the pleasure of hosting you for another excursion in the future. Happy to save some pizza for you and say hello to the fish...More

Reviewed January 24, 2017

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, responded to this reviewResponded January 26, 2017

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.

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Questions & Answers
April 9, 2017|
Response from SingingDogSailing | Property representative |
We are sorry but we will be unable to accommodate your group in October. Singing Dog Sailing closed annually that month for hurricane season wherein we haul our boats and schedule our annual preventative maintenance. Thank... More
April 7, 2015|
Response from SingingDogSailing | Property representative |
We are an inspected vessel recognized by the US Coast Guard to carry up to 12 passengers. Our itinerary choices and rates are listed in detail on the website. It would be our pleasure to host your group for a memorable... More