The story of sailing in Kissimmee is also a story of people—of fishermen, settlers, and local families who built their lives around the water. Before tourism became a major industry, Kissimmee’s economy depended on the bounty of its lakes. Catboat guides often shared stories about the early days of Kissimmee, when water transport was the lif

At the heart of the operation were the boats themselves—modern interpretations of a classic design. The catboats used for Kissimmee’s adventures were lightweight, two-seater sailboats powered by small electric motors for safety but primarily driven by wind. These vessels retained the hallmark features of traditional catboats: a wide hull for

Kissimmee’s connection to water runs deep. Situated in Osceola County, this historic town grew alongside Lake Tohopekaliga, the largest lake in the Kissimmee Chain of Lakes. The lake spans over 18,000 acres and has long been central to the community’s identity—first as a fishing and transport hub, and later as a center for tourism and wildlif

Florida’s expansive network of lakes, rivers, and coastal waters made it a natural destination for sailing enthusiasts. In the early 1900s, as tourism began to flourish, catboats found new life on the state’s calm inland waters. Boats that once worked the harbors of Massachusetts now drifted across Florida’s lakes, repurposed for pleasure