Barefoot Billy’s

Barefoot Billy’s has operated in Key West since 1992, running its jet ski tour business from two resort locations on the eastern side of the island, the Casa Marina Resort and The Reach Resort. Both properties sit along the Atlantic-facing shoreline away from the busier Duval Street corridor, giving the operation a quieter stretch of water to launch from than some of the harbor-based watersports companies closer to downtown.

The core lineup includes jet ski tours that loop guests around the nearby reef and channel areas, snorkeling tours for those who want to get in the water rather than just ride above it, sandbar charters for a more relaxed day anchored in shallow water, and parasailing for guests looking for an aerial view of the island and surrounding reef. Golf cart rentals round out the land-based side of the business, letting guests combine a watersports outing with easy transportation around the rest of the island.

Beyond the standard tour menu, Barefoot Billy’s also offers boat rentals, private charters, fishing charters, kayak rentals, and paddleboard rentals, effectively covering most categories of on-water recreation from a couple of fixed resort locations. Having built this range of services under a single brand over more than three decades gives the operation a well-established local identity, reflected in a large volume of accumulated customer reviews across travel platforms.

Operating from resort properties rather than a standalone dock or marina storefront reflects a common model in the Key West watersports industry, where beachfront hotels partner with tour operators to offer activities directly to their guests without those guests needing to travel elsewhere on the island. For visitors staying at Casa Marina or The Reach specifically, or anyone looking for watersports away from the more crowded harbor area downtown, Barefoot Billy’s three decades of continuous operation from these two locations represents one of the longer-running names in this particular corner of the Key West tourism economy.

Jet ski tours generally require riders to be at least a certain age to drive, with younger children typically allowed to ride as passengers behind a parent or guardian, a common structure across most Key West jet ski operators. Because both dock locations sit on the Atlantic side of the island, morning conditions here can differ from the calmer harbor water downtown, and guides typically adjust routes based on wind and chop on any given day. Parasailing flights are generally weather dependent as well, and the crew typically communicates any weather-related delays directly to guests staying at the two host resorts rather than requiring a guest to check in separately.