Books That Take Place in Key West

A one-time newspaperman for the Miami Herald, Carl Hiassen is the reigning king of the South Florida caper. With an opening line like this: “On the hottest day of July, trolling in dead-calm waters near Key West, a tourist named James Mayberry reeled up a human arm,” you won’t be putting this book down until the sun sets over the Gulf of Mexico.

Part of the Alex Rutledge mystery series, the streets, bars, and landscape of Key West is rendered so vividly that you could use Corcoran’s novel -and not the City Guide map of Key West -to navigate the Old Town as well as the hamlets off of A1A. While the book focuses on the corrupt underbelly of the island, it does so in a laid-back, breezy style. After reading the chapter that takes place in the Half Shell Raw Bar, a famous seafood shack in the Key West marina, head over and Eat It Raw for yourself.

While this 1937 novel is second-tier Hemingway at best, it’s notable for being the only novel Key West’s favorite son wrote that takes place in the United States. The book centers around Henry Morgan, a down-and-out fishing boat captain who gets mixed up smuggling contraband between Key West and Cuba.

Best described as an angst-fueled counter-culture portrait of Key West in the 70s’, Ninety-Two in the Shade is McGuane’s most famous novel. While the book was nominated for the National Book Award, it has largely fallen off the literary radar today. The novel follows Thomas Skeleton as he returns home to be a skiff guide in Key West, where he is forced to face a host of cultural and familial issues, not to mention a deadly male rival, all of which plays out like a tropical fever dream.

If you want a definitive portrait of Key West in the 70s, when Jimmy Buffett, Hunter S. Thompson, and Thomas McGuane went gonzo in the Duval Street bars, when creative inspiration and cargo holds of pot fused to form a sort of Paris in the Twenties bacchanalia, then this is the book. It’s the last call on America’s most famous tropical highway.