'Generous' Josh belittles the sailing abilities of his friend Terry O'Brien, and Terry counters by betting Josh $20,000 that, using an all-female crew, he can beat him in a race to Tahiti. Terry's crew consists of novice sailors - a murderess, a cocktail waitress, and two other women who go along for the ride - while Josh has an experienced crew. Josh bribes one of his women to sabotage Terry's boat, and despite numerous delays owing to an island jailbreak, a mutiny, a night spent overboard, and a romantic intrigue, Terry manages to close the gap between the rival sailing vessels; but Josh still finishes first. Josh's sabotage plan backfires, and he is forced to confess to his underhanded tactics, although he insists that he is the better sailor. Terry challenges Josh to a rematch, this time using a crew of baboons, Josh accepts, unaware that the "baboons" Terry intends to use are a Polynesian singing group composed of expert sailors.