Prep-schooler Dan Bartlett (John Cusack) is crushed when he fails a chemistry exam, preventing him from going on a Caribbean vacation with his girlfriend. At the last minute, his teacher passes him, and he sets off to meet up with the girl and her parents. Unfortunately, a series of travel misadventures causes him to remain several steps behind them. Circumstances lead him to become the first mate of a roguish sailor of fortune (Robert Loggia), who helps him try to catch up to his wayward lady love's boat. Meanwhile, she is busy fending off the unwanted advances of a comically persistent young man (Ben Stiller).
