In the "Escape" segment, Gregory Udall is an escape artist trying to get out of the shadow of his famous father by duplicating the solo ultimate escape his father performed, with Mr. Roarke providing the prison. Unfortunately for Udall, if you don't escape, well...you stay there forever. Udall manages to escape by overcoming his desire to do it single-handedly as he gets another prisoner to help him.

In the "Cinderella" segment, Ann and Maxine are working class girls who manage to afford a trip to Fantasy Island with a wish to become jet-setters for two days. They both get involved with rich men - Maxine ends up getting her man even when she confesses she's poor, and Ann ends up with a doctor pretending to be a rich millionaire to raise money for his health clinic.