Check out our sister site, Salty Dog Sailing!

Meet Your Crew.

St John Sailing Catamaran luxury Singing Dog Sailing Charters

Your Professional, Safe & Fun Crew Of Singing Dog Sailing Will Host You For A Memorable Day On The Water

Singing Dog Sailing caters to discerning guests desirous of exploring the delights of the US Virgin Islands and the British Virgin Islands in the height of sailing luxury.  Offering 1st class service, gourmet food and drink, all aboard a luxury sailing catamaran, your experienced captains will sail you away from the crowds  (or join them if that is your preference)  to specifically customized destinations in the US Virgin Islands and British Virgin Islands. With over 30 combined years of marine industry experience and being the only luxury day sailing charter in the local excursion business, we offer our guests the assured confidence that we are committed to making your day sailing with us the most fun and memorable of your vacation.

Meet Your Singing Dog Sailing Crew: Competent, Professional, Knowledgable & Fun

Polaroid of Admiral Jake

Admiral Jake

Admiral Jake joined our St. John sailing charters crew in 2005. He has led this ragtag bunch for thousands of sea miles in both the Atlantic and Caribbean Seas, visiting a multitude of countries and territories. His reputation as the bow-riding singing dinghy dog is known in the far reaches of outlying islands from the Chesapeake shores to the Keys in Florida, Bahamian Cays, Turks & Caicos Islands, Harbors of the Dominican Republic, Anchorages of Puerto Rico & his homeport of the Virgin Islands! The Coconut telegraph whispers his name often. Join the St. John sailing charter crew for a fun day aboard luxury catamaran ‘OFF CAY’ with Singing Dog Sailing and Admiral Jake! Check out his own Instagram account under his handle: @admiral_jake


Sailor Sandy

Sailor Sandy is the newest member of our crew! She joined up in 2015 and has counted on Jake to show her the ropes onboard Singing Dog Sailing. Sandy originally hails from Florida but earned her sea legs during Singing Dog Sailing’s 2016 journey from St. John all the way to Maine, a journey of 4,500+ nautical miles. Sandy loves a good dinghy ride, exploring a new beach and chasing her toy Lambchop all over the boat. She is also available as a snuggle buddy for naps. Check out Sandy’s Instagram here: @sailor.sandy


Polaroid of Captain Kelly

Captain Kelly

You will want to see Singing Dog Sailing’s Captain Kelly shine. She offers the best of guest relations!

Captain Kelly went on a fateful vacation more than 10 years ago and found inspiration in someone’s lust for life that was so palpable it was the proverbial “it” of happiness she was seeking. Leaving the business world of Organizational Psychology and pursuits of a Ph.D. behind, she ventured toward a life on the water. She became a PADI scuba instructor leading more than 5000 Discover Scuba divers during more than 1,700 dives per season while obtaining seatime toward her captain’s license qualifications which she obtained in 2002. She holds the same qualifications as Stephen and has skippered 30′ to 80′ vessels for private and commercial ventures. Trip Advisor is showered with praise about Captain Kelly in St John! Kelly also keeps our Twitter followers and Facebook Page fans pleased with fun photos, posts and tweets. Check out: @SingingDogSail on Twitter and Singing Dog Sailing on Facebook

Polaroid of Swab Stephen

Swab (Captain) Stephen

Captain Stephen is the true founder of this rabble, Singing Dog Sailing. He has been living aboard a boat since the mid-80’s. Graduating Texas A&M in Marine Biology, he took off sailing in his 20’s, single handling a 24′ C&C from the Texas coast to Nova Scotia and has been sailing the waters of the US Atlantic coast and the Caribbean Sea ever since. He holds a 100 ton US Coast Guard Master’s License with Aux Sail & Towing endorsements as well as STCW compliance for international voyages. He is a PADI Dive Master and holds current TWIC & First Aid/CPR certifications. He has skippered deliveries across the Atlantic to Bermuda and day charters on 30′ dive boats to 100′ wooden schooners. He is a natural sailor & a darn good guitar player too! Read guest comments about Captain Stephen and Singing Dog Sailing or catch him after sunset at St. John’s best venues like Aqua Bistro where he plays music on Fridays from 5:30-8:30!

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