St John USVI Sailing

Singing Dog Sailing's St. John based, private, luxury sailing catamaran- boasting superior amenities and performance sailing capabilities-is yours for the day to enjoy the best of the USVI, Virgin Islands National Park, USVI waters, cays and beaches around St. John or farther. As OFF CAY as you want to be! We suggest our signature Waterlemon Cay sail that primarily focuses on the US Virgin Islands National Park and St. John's north shore scenic Bays, Beaches and Cays. Join us for an idyllic day on the water exploring and sailing the magical US Virgin Islands.

JVD BVI Sailing

St. John Sailing Charters offers luxury sailing catamaran excursions for private groups to the nearby British Virgin Islands. Our luxury sailing catamaran is based and located in St. John, US Virgin Islands, which is less than 6 miles from Jost van Dyke, the closest British Virgin Island. Imagine visiting a different country by private charter! enjoy the most comfortable, spacious and stable ride to JVD aboard our first class sailing catamaran. there is no need to EARN your passport stamp, rather be pampered while sailing in style to the quaint neighboring BVI's.

Sunset Sailing

St. John luxury sailing charters with Singing Dog Sailing also offers the only first class private Sunset sailing option as well as custom multi-day sailing excursions. Celebrate the day's end with a toast at sunset aboard our luxury private catamaran. Featuring unrivaled amenities, service & experience. We take you as as "Off Cay" as you want to be for an hour, a day or perhaps longer. Let us help you plan a memorable experience on the water for you and your guests. It may be the same ocean, but it is not the best unless you try the Singing Dog Experience!

Luxury Private St. John Sailing Catamaran Charters

Singing Dog Sailing of St. John, US Virgin Islands, offers luxury, private sailing catamaran excursions departing from St. John and St. Thomas. Our luxury sailing catamaran, OFF CAY,  is St. John, US Virgin Island’s, only first class sailing and snorkeling charter. We exclusively book and host private groups for sailing trips to ensure the boat is your luxury sailing yacht for the day.

A first class charter with Singing Dog Sailing is also as “OFF CAY” as you want to be! We will take you off the beaten track to uninhabited destinations like Sandy Spit, BVI’s to enjoy nature’s bounty by sea, or to join the gang at Foxy’s Bar and The Soggy Dollar Bar  at  White Bay, Jost Van Dyke in the British Virgin Islands. Let Singing Dog Sailing, St. John, USVI,  take care of all the details while we host you for a memorable day on the water. Our exclusively private charter enables you to experience the beauty of the Caribbean like a native!  And let us not forget…In addition to our spacious, stable, comfortable, performance sailing catamaran, we also have an actual singing dog aboard OFF CAY as our fearless leader & Admiral. He is a very welcoming presence (sensitive to group dynamics by engaging or conveniently sleeping) and to most–the icing on the cake!

Join us to explore the Caribbean’s idyllic waters and cays of both the United States Virgin Islands and the British Virgin Islands aboard our sailing catamaran for an experience you will treasure for a lifetime. We cannot stress this enough: Come as guests; leave as friends, and live the dream with us for the day…or longer!

Our normal itineraries, which are all customizable, are based on a Cruz Bay, St. John, USVI, departure from the US Virgin Islands National Park Dock. However, Singing Dog Sailing conveniently hosts guests from either St. John or St. Thomas, USVI, also ensuring the most convenient itinerary options for your group. Our St. Thomas, USVI, Ritz Carlton Resort guests and Club owners may prefer a convenient pick up at the Ritz Carlton Resort Hotel Beach or Ritz Carlton Club Side Beach; St. John Westin Resort guests or owners may be picked up at the Westin Resort Beach and St. John Caneel Bay Resort guests may be picked up at the Caneel Bay Resort–whatever is most convenient for your group and your desired itinerary for a luxury day sail excursion.

Your day with Singing Dog Sailing will be similar to an expertly prepared and attentively served fine dinning experience at ZoZo’s Ristorante at the Sugar Mill, Caneel Bay Resort, or a Magic Moments luxury powerboat charter; the Singing Dog Sailing charter experience is an equally unparalleled sailing trip excursion.  We collectively & consistently offer, thus making us leaders in our respective niche:

  • first class service with unparalleled experience (It’s YOUR yacht with an expert crew);
  • superior amenities (shaded seating for up 12 on an almost million dollar yacht if bought new);
  • impeccable cleanliness (not a stripped down commercial “cattle-maran” that you rent privately and pay a minimum of 18+ pax);
  • obvious detailed maintenance (disinfected, washed and detailed between every charter);
  • prepared attitude of paramount safety measures & top quality equipment;
  • licensed & insured (many are not or do not carry same policy limits).

Please consider reviews on and note the excellent, 5 star reviews for ZoZo’s, Magic Moments and Singing Dog Sailing–you may be certain that when first class is what you seek as a discerning guest, you will only find that level of consistent service and overall–never fluctuating, first class experience at certain venues.  Although every level of charter option may be listed under’ things to do’ in St. John and subcategory of ‘activities’ on that Trip Advisor feedback forum, you can sift through the inflated ranking numbers of “cattlemaran” style boats that focus on volume, rather than quality, the un-related category of little runabouts that lack amenities which a more discerning guest is seeking and finally multiple monohulls which boast small group sizes, but which vessels are inferior in comfort, size, amenities etc–there are 1-2 other private cats who boast similar, but we can assure your that NONE have a refit boat of our caliber, cleanliness to our degree, experience to our level and overall professionalism that is unmatched.  Although we are all lumped together on one list, it is unfortunately like comparing a coach seat on a commercial airline to a private Gulfstream Jet. We at Singing Dog Sailing, are at the top of the hierarchy if you only consider our level of excursion.

Additionally, since we only host private groups and do not overbook our boat, we will never have the volume to compete with sheer numbers of reviews–purposefully.  This only benefits our guests as we take pride in limiting trips offered each week thereby ensuring detailed cleaning and expert maintenance between charters, and possible alternate sailing dates should we wish to consider weather preference–NO OTHER CHARTER CAN SAY THE SAME; they are all RAIN or SHINE. The only way to achieve a first class trip experience on a vessel of our quality and degree of cleanliness is to NOT overbook.  You are not just a number or a dollar sign with us.  We love what we do and want to share it with those whom will love it as much as we do! please note that 90% of our guests book yearly. it is advisable to email us as soon as you begin to make your USVI vacation travel plans. We normally book 30 days in advance and up to 6+ months in advance for major holiday weeks.

We invite you to the Singing Dog Sailing Experience and trust that after one day with us, no other boat will ever be acceptable again!

Our goal, at Singing Dog Sailing of St. John, is to treat you like you are the owners of your own million dollar yacht sailing catamaran for the day and we are your welcoming captains hosting you on your own private sailing day trip.  Unlike many charters in the market wherein dreamers buy boats and get captain’s licenses with little to no experience, maybe just deep pockets–(and unlike Singing Dog Sailing, some not even licensed or insured), you benefit from your fun, yet professional & expert crew with more than 45 years of collective, advanced sailing experience around the world and 28 collective years chartering experience here in the USVI and BVI’s.  Read our crew biography section of this website to gt to know they friends you have yet to meet as we each have fun stories about where we came from and how we got here.  As part of our promise, you will be welcomed as a guest and leave as a friend with desires to come back soon on your next Singing Dog Sailing adventure.

As a final welcoming note to the Singing Dog Sailing experience: It may be the same ocean with similar destinations like the US Virgin Islands National Park featuring stops at Waterlemon Cay, Maho Bay, Trunk Bay, Whistling Cay, Lovongo and Henley Cays as well as BVI destinations like Jost van Dyke ( JVD) — home to the Bubbly Pool, Foxy’s and the Soggy Dollar Bar to name a few, Sandy Spit, Smuggler’s Cove on Tortola or Pirate’s Bight and the famous Willy T at Norman Island, but you will only enjoy first class, attentive service, superior amenities and professional expertise aboard OFF CAY, St. John’s only luxury sailing catamaran. With our considerate expertise, we will help you tailor a day itinerary that meets your expectations for the most memorable day of your vacation.

We recognize that we are not for everyone–So if you are only seeking a ride from pont A to B, or worried about price, still contact us as we offer no-fee booking services. With our fingers on the pulse of all things boating, we can find a good fit for you, even if it is not aboard OFF CAY on this trip–if more affordable sailing is your goal then perhaps the alternate option of our sister monohull sailboat, which is St. John’s classic, yet affordable charter, may be better suited:, just to name one of many options.  Whatever your needs, we are happy to consult with you as a boating concierge to ensure you have a great day on the water no matter with whom.

On the open seas with Singing Dog SailingOn the open seas with Singing Dog SailingOn the open seas with Singing Dog SailingOn the open seas with Singing Dog Sailing

Book Your St. John Sailing Charter Today!

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