Hollywood, 1930s. Tod Hackett, a young painter who tries to make his way as an art director in the lurid world of film industry, gets infatuated with his neighbor Faye Greener, an aspiring actress who prefers the life that Homer Simpson, a lone accountant, can offer her.

Two teenagers set out on a 2000-mile sailboat journey from California to Hawaii and en route combat the natural challenges and their inner shortcomings.