Bamboo Bob is a small time DJ broadcasting from his bedroom. When his Trop Rock radio station is nominated for an award, his wild cousin Steve hatches a plan to sneak the pair down to Key West to attend the ceremony, before Bob's impending job interview. Things get complicated when he meets one of his biggest fans who shows him what life in the Keys could be like. Bob finds he has to choose between the life he's living, or the one beyond the beach he's only dreamed of.

Chasing the Sun

A newly single guy meets an offbeat girl after posting his dating manifesto online. As the two spend a weekend together in a pretend relationship, a connection grows that may complicate their real lives.