Singing Dog Sailing

  • Singing-Dog-Sailing-catamaran-OFF-CAY-1

Business Category: Charter Boats, St.John, and SailingBusiness Tags: charter boats and sailing

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  • St. John’s ONLY First Class, Luxury Sailing Charter

    Offering trips in USVI (Virgin Islands National Park) & BVI’s (Jost van Dyke). Private groups only 1-12 guests. Superior amenities, attentive service, performance sailing and major fun.This charter boasts superior amenities and performance sailing capabilities. A Singing Dog Sailing charter is like owning your own private catamaran for the day. Enjoy the best of the USVI when sailing with Singing Dog.  Highlights for US Waters trips include the Virgin Islands National Park, USVI waters, cays and beaches around St. John or farther–As OFF CAY as you want to be! Join us for our Signature Waterlemon Cay sail to experience an idyllic day on the water exploring and sailing the magical USVI while aboard your own private catamaran.


    Looking for an affordable day sail option? Check out our partner charter biz, Salty Dog Sailing

    Check out our partner charter biz, Salty Dog Day Sails.


    Captain Kelly shares her expert advice on Sunscreen and protecting our reefs. Have a read and find out for yourself what to look for in sun protection.


    ♥ Share the VI Love ♥
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  • 8 Reviews on “Singing Dog Sailing”

    1. Mackenzie Singing Dog Sailing

      This is the third year that my family has booked with Kelly and Stephen, and we can never seem to get enough. These two are so much fun to be around that you feel as though you are old friends or family. Each charter seems to top the year’s before! They are so professional, yet also laid back. Being able to create your own itinerary and customize the trip is amazing!! It is 100% worth the money. Always a treat and something that my entire family looks forward to.

    2. Anita Singing Dog Sailing

      We had a wonderful day of sailing with Stephen & Kelly! I would definitely recommend them to anyone who’s visiting St. John!!

    3. Megan Burgoyne Singing Dog Sailing

      Every trip I have been on with Captains Kelly and Stephen has been more memorable than the last. They always have a new beach, snorkeling spot, restaurant, or bar to show us. No trip is the same but each is relaxed, fun, and memorable!

    4. Tracy Singing Dog Sailing

      We had a very memorable day with Stephen and Kelly. We have done similar trips in Maui, Grand Caymen, and St. Thomas and none have even come close to what they offer. Stephen is a marine biologist and was full of helpful and interesting information about the things we saw. By the end of our day we were having so much fun that we extended our sail to include sunset and we joined Stephen and Kelly at a bar in town to hear Stephen perform. I would highly recommend chartering this boat, our group included three generations and we all loved it. Stephen was very caring and helpful with my mother-in-law who was in her seventies and had never been in the ocean before.

    5. Lois R Patton Singing Dog Sailing

      On several occasssions I have had the privilege of sailing with Captains Kelly & Stephen . Off Cay is always pristine and the food is scrumptious–plus you have Jake & Sandy to pet. I feel welcomed and adored–a nice blend of being family, but also royalty. I celebrated my 50th birthday with sisters & girlfriends while island hopping the BVIs with Singing Dog Sailing–while the sun was not always shining (even Kelly & Stephen have no control over the weather)–my group had a wonderful time relaxing, laughing, snorkeling and enjoying life. I promise you will not be disappointed and you will be planning your return visit!

    6. Raquel Mello Singing Dog Sailing

      You will not have a better day at sea! From the moment you step on board you are greeted with smiles and the smell of fresh cinnamon rolls! You can customize your trip any way you want and no matter where you end up you can’t go wrong. Captain Steve is the best guided snorkeler you could ask for and takes some of the nicest pictures you get to keep as souvenirs. Make the Soggy Dollar Bar a stop no matter what you do!!! And then enjoy, sit back with your Pain Killer on the front nets of the boat as you soak up the sun around the BVI’s!!!

    7. Barb Young Singing Dog Sailing

      I have had the pleasure of spending a few different occasions out on the water with Captain’s Kelly and Stephen. They are top notch. The vessels are spotless and gorgeous. You will have an amazing day on the water with them and their crew. Their knowledge of the waters above and below are unmatched. Can’t wait to do it again!

    8. Megan Singing Dog Sailing

      Captains Kelly and Stephen took me over to Jost van Dyke for an amazing birthday trip. I don’t know how they manage to be so laid-back and fun all at the same time, but I had a blast with them. We did lunch at Sydney’s, then a relaxing day on the beach at White Bay, watching the boats go in and out. And, of course, their boat is simply gorgeous, so the ride over and back is at least half the fun. Thanks for a wonderful day on the water. The days I spend with Kelly and Stephen are always the most memorable. I highly recommend sailing with them, whether you want to do beaches, snorkeling or simply some exploring. (Ask Stephen to find you a jawfish!)

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