High school student Dan Bartlett (John Cusack) misses the plane he was supposed to be on with his rich girlfriend and her family on the way to a Caribbean vacation during a school break. He flies there alone, and runs into a series of characters and misadventures as he tries to catch up. Cannabis (drug)-smoking island natives give him a lift in their vehicle, but they don't quite make it as the family takes off on a chartered yacht. A crusty old sailor (Robert Loggia) with his own reasons takes up the chase with Bartlett on a decrepit sailboat. Bartlett then runs into corrupt cops and winds up in jail. Finally, he catches up to the yacht, only to find that the family has been taken hostage by pirates. He comes to the rescue.