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. Ganja-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 high school student named Dan Bartlett (John Cusack) misses his flight to a Caribbean vacation with his wealthy girlfriend and her family, flying there alone after the plane leaves without him. He encounters various characters and mishaps as he attempts to catch up.  Island natives who smoke marijuana give him a ride in their vehicle but they don't make it as the family departs on a chartered yacht.