Captain Justin Smith
Justin was born in Connecticut, a state saturated in oceanic history; but, if you ask him he will tell you he is from the ocean, “home is where the anchor drops.” Unlike most young American men, Justin was raised mainly by his seafaring grandparents and received an education whilst they sailed up and down the Eastern Coast of the United States.

The world has been Justin’s oyster and he was privileged enough to have spent his youth in various countries and honed his captain’s education in a myriad of maritime schools. A skilled sailor, he received his master’s license at the juvenile age of only sixteen; he was unable to escape the call of the ocean. As a young man, Justin exhibited a passion not only to sail the seas, but also to rebuild classic boats. His first large project was the restoration of a classic fiberglass boat, a vessel which enabled him to start his adult maritime career. He sailed south towards not only the Caribbean, but onwards to a life of adventure and self-fulfillment.

During his time in the Caribbean, Justin captained several yachts and began his profession in yacht charters. 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. The love for his craft shows not only in his expertise of the seas, but also in riveting conversations with guests about boats, the ocean, and all things nautical!

At the helm, Captain Justin likes to take his guests to off the beaten path locations, catch lobsters and makes fresh conch salads. Come sail with Justin and explore the hidden treasures of the islands, he’ll show you a world traversed by only a few.


First Mate Lecil James
Born and raised in the arid deserts of southwestern Colorado, Lecil has swapped desert and mountains for the endless horizon of the ocean. She has always prioritized letting her passions lead her through life. After earning an advanced degree in theater and sculpture, Lecil spent her early career traveling the world, working in theater production, hospitality and regenerative farming. 

Lecil came to sailing much later in life. Amid the pandemic, she found herself on Cape Cod, Massachusetts, where she joined the crew of a commercial schooner. She offered day sails to tourists whilst moonlighting as a beachfront lifeguard and thought life couldn't get any better. That is, until she learned about the amazing world of term charters and the opportunity to combine two of her favourite hobbies: sailing and cooking. She fully embraced the call of the sea and joined the team on Kai full time in 2024. A true adventurer at heart, Lecil thrives on exploring the diverse places Kai visits, diving deep into local cultures and savoring regional delicacies along the way. When not in the galley, she’s probably somewhere in the water trying to find the perfect shell to show Justin. ​


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 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.