Pink Marble




Captain Justin Smith will greet you with smiles, cold cocktails and hors d'oeuvres when you arrive for your vacation. What are you waiting for? Come let us sail you through the Virgin Islands on your own customized trip! 


Meet the Captain

Justin was born in Connecticut, a state saturated in oceanic history. However, if you ask him, he will tell you he is from the ocean since “home is where the anchor drops.” Unlike most young American men, Justin had a unique upbringing. He was raised mainly by his seafaring grandparents, and received an education while 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 while honing his captain’s education at a myriad of maritime schools. A skilled sailor, he received his master’s license at the age of only sixteen. As a young man, Justin exhibited a passion not only for sailing the seas, but also for rebuilding classic boats. His first large project was the restoration of a classic fiberglass boat, a vessel that enabled him to start his adult maritime career. He sailed south towards the Caribbean, and to a life of adventure and self-fulfillment.  

Since beginning his profession in yacht charters in 2010, Justin has captained several yachts and now has more than 11 years of experience in the charter business. The love for his craft is shown not only in his expertise of the seas, but also through 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 make fresh conch salads. If you are lucky enough to sail with Justin, you'll get to explore the hidden treasures of the islands and be shown a world traversed by only a few.


Meet Deckhand Sam

Sam is a St. John COVID-19 rescue dog. During our lockdown here in the USVI, we decided we were going to foster a puppy to help the overwhelmed shelters. A week later, she had become an invaluable member of Kai's crew, and would call Kai her forever home. While running her first charter only a month later, it became clear that she knows how to win the crowd. A few weeks later, Sam crossed the North Atlantic on a nonstop eight-day trip from USVI to Newport, Connecticut, where we spent the summer doing "dirty boatyard work and learning all the boat things." She proved her skills that fall 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.


After all of Sam's miles, she has more than a dozen charters under her belt. Sam is a very laidback pup, listens extremely well, doesn't beg, and feels the vibe. At only 19 pounds, she blends in and most days you hardly even notice she's there. Sam is gentle with kids. She loves going for swims, walks on the beach, and snuggling if you're up for it!