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Singing Dog Sailing

Features Animals
Cruz Bay 00831, St. John
+1 340-244-8230
Review Highlights
Another World

We just completed a fantastic trip through the BVI's on a multi day sail. Everything is perfectly... read more

Reviewed 1 August 2017
john k
Des Moines, Iowa
Simply the best

Absolutely amazing trip, crew and experience. Justin and Pepper treated us right. I promise that... read more

Reviewed 26 July 2017
Houston, Texas
via mobile
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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1 - 10 of 148 reviews

Reviewed 1 August 2017

We just completed a fantastic trip through the BVI's on a multi day sail. Everything is perfectly timed with tremendous snorkeling stops where the Captains help you discover marine life that many would miss. The boat is pristine and the plenty of room to relax...More

Thank john k
Reviewed 26 July 2017 via mobile

Absolutely amazing trip, crew and experience. Justin and Pepper treated us right. I promise that you will love everything about your trip with these guys. From my first contact with them by phone to our final handshake at customs after reentering the US, they took...More

Thank jimmY3405WJ
Reviewed 7 July 2017

I've been on Off Cay, the larger catamaran and now it was time to sail on Little Dog. We were a group of six that Captain Kelly and first mate Meagan took on a half day sail and snorkel. This boat is perfect for smaller...More

1  Thank sv b
Reviewed 27 June 2017 via mobile

I am a Sunset enthusiasts and this Sunset Sail was 10 plus I can't say enough wonderful things about Captain Kelly and Captain Steve. Look at the color palette! We had more fun and laughter on board this Immaculate catamaran . Will definitely do this...More

Thank MermaidGypsea
Reviewed 24 June 2017 via mobile

We were looking for the perfect mix of relaxation, adventure, and island vibes... and Sailing Dog delivered in spades. Plus, they literally have two happy puppies running around. Doesn't get much better than ice cold cocktails, crystal blue waters, catamarans, and cool captains that just...More

Thank Dan L
Reviewed 20 June 2017 via mobile

After a five star experience aboard Singing Dog two years ago, we booked them again this year and, of course, were over the moon satisfied!This wonderful couple quickly became our friends and gave us such a wonderful day, it felt like we were spending time...More

Thank gabbyloulou
Reviewed 14 June 2017

Is there a place to give a 6-star rating? If there was, Kelly and her beautiful sailing boat excursion would get that from me. Instead, I guess I must settle for 5-stars! She is a very adept and knowledgeable captain, and her boat is very...More

Thank Rick S
Reviewed 23 May 2017 via mobile

I have sailed with Kelly and Stephen on Singing Dog many times. They offer expert sailing and knowledge of the Virgin Islands. This year we chartered Little Dog and had a cute mate named Pepper. Pepper is very knowledgeable and a perfect fit. This charter...More

Thank Denise P
Reviewed 16 May 2017 via mobile

Kelly and Stephen were the perfect hosts and created an amazing experience we will never forget! The boat was beautiful, the food and drinks were delicious, and the snorkeling was (and is) the best in the Caribbean. Stephen's knowledge of marine life allowed us to...More

Thank Gigi M
Reviewed 15 May 2017 via mobile

Had a great time at sea with Kelly, Stephen, and their cute pups! Excellent day activity on the island! If you're looking for an intimate experience with two amazing guides, this is the sailing experience for you!

Thank Tim K
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Questions & Answers
10 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
8 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