Captain Ron

Captain Ron is a 1992 film starring Kurt Russell and Martin Short. A family in Chicago inherits a yacht formerly owned by Clark Gable. They decide to sail it from the Island of Ste. Pomme de Terre to Miami and hire a local, Captain Ron, to sail it for them. He guides them from island to island in the treacherous Caribbean, making friends with revolutionaries, partying with the locals, and running afoul of the dreaded "Pirates of the Caribbean."