Singing Dog Sailing


Luxury Sailing Catamaran Charters

Singing Dog Sailing is St. John’s only luxury sailing catamaran charter. Discerning guests prefer the amenities, service, Crew experience and performance capabilities of this top-of-the-line and spacious catamaran.

You do not have to rub elbows unless you want to.

Come enjoy a memorable day exploring the USVI’s and BVI’s by water with Singing Dog Sailing aboard luxury catamaran ‘OFF CAY.’

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Luxury Amenities & Service

Boutique sailing at it’s best, discerning guests will enjoy first-class, luxury amenities and service during a memorable day on the water exploring the Virgin Islands. St. John’s Singing Dog Sailing luxury catamaran ‘OFF CAY’ is a top-of-the-line, spacious sailing catamaran with all of the accouterments expected of a first-class charter.

The Singing Dog Sailing experience is notches above the rest.

Highlights include:

  • Professional mariners with 20+ years local US Virgin Islands and British Virgin Islands charter experience and educated backgrounds. Capable seamanship and luxury service orientation; captains and crew capable of providing a safe, yet enjoyable context for your group to unwind.

  • Not your typical Caribbean catamaran experience — Performance sailing capabilities, first-class amenities and show-room-floor cleanliness are all key features of the Singing Dog Sailing luxury catamaran charter experience with group sizes limited to 12 passengers only.

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USVI and BVI Itineraries

Singing Dog Sailing luxury catamaran ‘OFF CAY’ hosts full day USVI & BVI sailing charters for private groups of up to 12 passengers.

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10AM-4PM Virgin Islands National Park Snorkel Sail. Signature ‘reef fish encounter’ and ‘swim with the turtles’ guided snorkeling experiences. Weather permitting stop at Waterlemon Cay.


10AM-4PM Off-The-Beaten-Path neighboring cays snorkel sail with lunch stop at PizzaPi at Christmas Cove Great St. James. Trips focus on sailing and snorkeling to places you cannot access by car.


9AM-4PM. Get another stamp in your passport on our JVD snorkel sail. Trip includes brief visit to Foxy’s in Great Harbour then afternoon fun at White Bay, home to the infamous Soggy Dollar Bar.





Sunset celebrations or half day snorkel sail excursions. Unique yet abbreviated sailing itineraries.


“Living the dream and sharing it with guests who will love it too .”

kelly quinn  |  owner, Singing Dog Sailing


St. John Hurricane Survivors

As many are aware, St. John and the neighboring Virgin Islands suffered direct impacts from Hurricanes Irma and Maria. Singing Dog Sailing lost several boats in the fleet, but saved the flagship luxury catamaran ‘OFF CAY’ by departing 12 hours before each storm made landfall in St. John and Puerto Rico respectively, riding out the ferocity of each storm sailing through squall bands to reach distances of 160-200nm out in the middle of the ocean with the ultimate goal of being in less than 50kt wind bands for safety. The Captains came back to unimaginable destruction in St. John and persisted tirelessly in search and recovery missions and to ensure safety, medical attention and rescue was accessible to those in need.


Putting the loss of their other vessels in the background of importance, they directed all offers of personal charity support to verified community organizations rather than accept self-interest support of direct monetary donations and apart from a handful of charters in 18 months, the owners worked without income and with insurance payout of only 50% of invested loss to rebuild their fleet using their own labor and financial reserves now fully depleted. Being so committed to their presence within the community, they chose not to take the easy and softer way of relocating and starting afresh elsewhere, but chose to risk the long-haul commitment to St. John and its recovery.

The owners of Singing Dog Sailing thank you for your support in your visit to this island they consider paradise.







Singing Dog Sailing

St. John Luxury Sailing Catamaran Charters

USVI & BVI Itineraries for private groups of up to 12 passengers on private charters.