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Singing Dog Sailing

Features Animals
Cruz Bay 00831, St. John
+1 340-244-8230
Review Highlights
Play it Again

We retuned to the Islands and made certain to book in advance a trip with Stephen & Kelly and Jake... read more

Reviewed 14 February 2014
john k
Des Moines, Iowa
Wonderful Day

This was the best day of our trip. Stephen and Kelly are wonderful hosts as well as captains. From... read more

Reviewed 30 January 2014
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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Travellers talk about
“admiral jake” (23 reviews)
Suggested Duration: More than 3 hours
Cruz Bay 00831, St. John
+1 340-244-8230
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Reviews (148)
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61 - 70 of 148 reviews

Reviewed 14 February 2014

We retuned to the Islands and made certain to book in advance a trip with Stephen & Kelly and Jake. This was as delightful if not more so that the last trip. Their hospitality is fantastic, we had a great day of snorkeling sailing and...More

Thank john k
Reviewed 30 January 2014

This was the best day of our trip. Stephen and Kelly are wonderful hosts as well as captains. From the excellent service, to the hearty deli lunch, to the well kept boat, everything was perfect. Because of a break in the weather they were able...More

Thank ScubaKaren
Reviewed 26 January 2014

I think the title should sum it up. I have been to St. John many times, but never experienced the Virgin Islands like the day we went out with Kelly and Stephen. Not only are they great sailors showing us the most beautiful sites, they...More

Thank Gabriel R
Reviewed 26 January 2014

If you have read my previous reviews you will all know how much we love Kelly, Stephen and Jake. However this November this crew of uniquely special people gave me the greatest wedding gift i could have asked for other then my wife. 13 Hours...More

Thank Aaron C
Reviewed 20 January 2014

Been coming to St. John for 4 years now and always have to go sailing on Singing Dog! It's a must do for all ages! Kelly, Stephan and Jake are the best!!! The boat and crew are amazing and they truly take pride in what...More

Thank Stacy G
Reviewed 17 January 2014 via mobile

My husband Vince and I paid our first visit to this beautiful island between Christmas and New Years. Needless to say this is just the beginning of many more visits. The weather was terrific, restaurants were outstanding, our accomodations at the St. John Inn were...More

1  Thank astronyc
Reviewed 1 January 2014

This was my 3rd trip and best trip with Singing Dog. Kelly,Steven and Jake are the best and accommodate whatever the need. We had a group of 8 girls celebrating the 50th birthday of my sister. They sailed us to Jost, Marina Cay, Virgin Gorda,...More

Thank Denise P
Reviewed 1 January 2014

Beautiful boat kept in pristine condition, spectacular sail and laid-back hosts who make great company - we (grandparents, parents and kids 13, 10 and 8) had an absolutely wonderful day!

Thank WF E
Reviewed 16 December 2013

My husband and I had an incredible day with Singing Dog Sailing during our honeymoon in Saint John. It was by far the highlight of our trip! Captains Kelly and Stephen were so friendly, knowledgeable and accommodating. We were welcomed by a delicious breakfast when...More

1  Thank Rachel P
Reviewed 28 November 2013

We just returned from a truly wonderful day sailing with Captain Kelly & Steve and there super cute dog Jake. Kelly & Steve were not only terrific sailing guides but wonderful hosts for our family trip. We had an infant on board and our hosts...More

Thank SaratogaGuy
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Nearby Attractions
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Questions & Answers
9 April 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
7 April 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