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Captain Justin Smith


    Home is where the anchor drops.

Originally born in Connecticut, Justin was raised primarily by his seafaring grandparents – and spent his youth sailing up and down the eastern coast of the United States and traveling to various countries. A skilled sailor, he attended several maritime schools to continue honing his expertise and earned his master’s license at the young age of 16 – an incredible accomplishment. Since beginning his profession in yacht charters in 2010, Justin has captained several yachts and has over 11 years of experience in the charter business.


His passion for sailing the seas also includes a love for rebuilding classic boats. His first large project involved the restoration of a classic fiberglass boat, which began his adult maritime career as he sailed south towards the Caribbean to a life of adventure and self-fulfillment. At the helm, Captain Justin loves having the opportunity to sail guests to off-the-beaten path locations, and giving them a chance to explore the hidden treasures of a world traversed by only a few.

Deckhand Sam


Originally a St. John COVID-19 foster pup, Sam is now a permanent and invaluable member of Kai’s crew. While running her first charter, it became clear that she knows how to win over a crowd. A few weeks later, Sam crossed the North Atlantic on a non-stop, eight-day trip from USVI to Newport, Connecticut where we spent the summer doing “dirty boatyard work and learning all the boat things.” The following fall, she proved her skills on a 14-day passage upwind back to the USVI before running a very productive 2021 charter season (she now has over a dozen charters under her belt). She also stole the show during the filming of “Knowing You” by Kenny Chesney with her sweet, laidback nature.


At only 19 pounds, most of the time you won’t even notice that Sam is there (unless of course you’re up for joining her for a swim, snuggle, or walk on the beach – she loves those). Sam is gentle with kids, doesn’t beg, and listens extremely well.

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