"The Rum Diary" tells the increasingly unhinged story of itinerant journalist Paul Kemp. Tiring 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 newspaper, The San Juan Star, run by downtrodden editor Lotterman. Adopting the rum-soaked life of the island, Paul soon becomes obsessed with Chenault, the wildly attractive Connecticut-born fiancée of Sanderson. When Kemp is recruited by Sanderson to write favorably about his latest unsavory scheme, the journalist is presented with a choice: to use his words for the corrupt businessmen's financial benefit, or use them to take the bastards down.