The increasingly unhinged story of itinerant journalist Paul Kemp (Depp). Tired of the noise and madness of New York and the crushing conventions of late Eisenhower-era America, Kemp travels to the pristine island of Puerto Rico to write for a local San Juan newspaper run by the downtrodden editor Lotterman (Jenkins). Adopting the rum-soaked lifestyle of the late '50s version of Hemingway's "The Lost Generation," Paul soon becomes entangled with a very attractive American woman, Chenault (Heard) and her fiancee Sanderson (Eckhart), a businessman involved in shady property development deals. It is within this world that Kemp ultimately discovers his true voice as a writer and integrity as a man.