Paul Kemp (Johnny Depp) is an aspiring author who hasn't been able to sell a book. Instead, he applies for a job at a newspaper in San Juan, Puerto Rico. He gets the job and meets Sala (Michael Rispoli), who gets him acclimated and tells him he thinks the newspaper will fold soon. Kemp is given the horoscope section. He's staying at a hotel and meets Chenault (Amber Heard), who's avoiding a Union Carbide party there. Kemp is immediately smitten with her.
Kemp is an alcoholic and his boss Lotterman (Richard Jenkins) tells him to stop drinking. Kemp also meets Moberg (Giovanni Ribisi), a deadbeat who can't be fired. Waiting for an interview, Kemp meets Sanderson (Aaron Eckhart), a freelance realtor, who takes him home to discuss Kemp writing ads for him. Chenault is Sanderson's fiancee, but pretends not to know him.
Kemp moves in with Sala, who also rooms with Moberg. The place is horribly unkempt and poor. Sala keeps cockerels for cockfighting. Kemp begins to see the poverty of San Juan, but his boss doesn't want him to write about it, as it's bad for tourism. Moberg returns with leftover filters from a rum plant containing high-proof alcohol. Moberg has been fired, and wants to kill Lotterman. He also likes Nazi records.
Kemp visits Sanderson and spies him making love to Chenault. He meets Zimburger (Bill Smitrovich) and Segarra (Amaury Nolasco), who want him to help with a real estate scam. Sanderson yells at some locals who are walking onto his beach. Later, Sala and Kemp are driving, and the locals attack them. The police arrive and break up the fight, then throw Sala and Kemp in jail. Sanderson gets them out.
The next day, Kemp meets with Sanderson's crew, who tell him that the US military is relinquishing the lease on some prime real estate, and he is asked to pick up Chenault from her house. They share a moment.
Zimburger takes Kemp and Sala to see the island property, then they head to St. Thomas for Carnival. He finds Chenault, and they wind up on Sanderson's boat. Sanderson is unhappy that Sala is involved. At night, they go to a club, and Chenault dances with locals, which enrages Sanderson even more.
The next day, Chenault is gone, and Sanderson tells Kemp that he blew it. When Salas and Kemp return home, Moberg tells them that Lotterman has left. He also sells them some drugs, which they take. In an rum- and drug-induced stupor, they wander about the docks. Kemp works on a newspaper story.
Lotterman returns, but won't publish Kemp's story. Chenault shows up at Kemp's place, and Sanderson disowns her. Sanderson withdraws his bail, and Kemp and Sala are wanted. Moberg also tells them that Lotterman has closed the paper. Kemp decides to print a last issue, telling the truth about Lotterman and Sanderson, as well as the stories Lotterman declined.
To gain money to print the last edition, Kemp, Sala, and Moberg place a big cockfighting bet. They visit a hermaphrodite witch doctor to lay a blessing on their cockerel. They win, but the newspaper machines have been confiscated. The dream dies.
Kemp continues his quest, stealing Sanderson's boat. The end credits explain that Kemp made it back to New York, married Chenault, and became a successful journalist.