About Barefoot Billy's
Barefoot Billy's has been a Key West fixture since 1988, when founder Billy started out as the island's most persistent suntan lotion salesman on the beach. By 1992 the business had evolved into something far more ambitious: the first-ever guided jet ski tour to circumnavigate Key West, a 26-mile route that remains the company's signature experience to this day. That pioneering spirit turned a one-man beach operation into one of the island's most recognised watersports brands, now running out of prime resort locations on the south shore.
Their primary base sits at the Casa Marina Resort on Reynolds Street, where guests walk straight off the sand and onto a jet ski — no shuttle or marina transfer required. A second location at the Reach Resort offers the same beachfront convenience just a short stroll away. Beyond the flagship Island Jet Ski Tour, the lineup includes catamaran sunset cruises, reef snorkeling excursions, sandbar trips, parasailing flights, and kayak and paddleboard rentals, giving visitors a full menu of on-water activities without leaving the resort grounds.
Barefoot Billy's also operates a concierge desk that helps guests book restaurants, nightlife, and other Key West excursions, positioning the brand as a one-stop resource rather than just a watersports vendor. Their guided tours cap group sizes to keep the experience personal, and the resort-based setup means families with young children can easily move between the beach and the activity counter throughout the day. For anyone staying on Key West's quieter south side, Barefoot Billy's eliminates the need to trek to the crowded Historic Seaport for a quality watersports experience.
