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Chasing the Literary Ghosts of Key West

Key West famous author's house
Key West is famous for its authors. And while you can, of course, head to one of the many homes that have been enshrined as living tributes to their former literary inhabitants. There are a few spots off the beaten path that will show you there’s more to Key West’s literary history than the iconic Whitehead Street Ernest Hemingway House.

A Tale of Hemingway’s Two Sloppy Joe’s

Die-hard fans of Ernest “Papa” Hemingway will naturally want to tour his former home on Whitehead Street, now a museum populated by 40 to 50 six-toed cats (allegedly descendants of Hemingway’s own six-toed cat, Snow White). But to get a better feel for the real essence of the legendary author, you’ll need to do a little drinking. Indeed, in Key West, it’s not hard to find a barstool that Hemingway once occupied. In order to hang out at his favorite neighborhood watering hole, you’ll actually need to visit two Key West bars, now dueling over who gets the right to Hemingway’s notoriety. Hemingway frequented Sloppy Joe’s in the 1930s, both in the current Duval Street location but also in the Greene Street location, which now houses Captain Tony’s Saloon. Both bars like to claim they’re the original Sloppy Joe’s so beloved by Papa Hemingway, but you’ll have to decide where you feel his spirit most yourself.

The Bookstore that Judy Blume Built

Author of seminal coming-of-age works, such as Are You There, God? It’s Me, Margaret, Judy Blume is no stranger to what makes a good bookstore. Living in Key West since 2004, Blume helped launch Books & Books @ The Studios of Key West in January of 2016, which filled a need for a “locally owned, nonprofit, independently minded neighborhood bookstore” in Key West (considering the rich literary history of the island, Blume and her author husband, George Cooper, felt compelled to bring one to town). Head down their location, housed in the The Studios of Key West and a former Masonic Temple, to browse their titles or attend an author’s event – you might just brush shoulders with Ms. Blume herself.

The Bicycle Eating Tree That Belonged to Shel Silverstein

At 618 William Street, you’ll find an impressive Greek Revival house and writing studio that once belonged to Shel Silverstein, the beloved author of children’s literature. You’ll also find a massive banyan tree. Legend has it that Silverstein once leaned a bicycle against the tree for an extended period of time while he was out of town, only to return some time later to find that the banyan tree had gnarled itself around the bicycle, lifting it off the ground. The bicycle, which is now completely entombed within the tree, used to be partial visible as it hung suspended mid-tree trunk.

The Begged and Borrowed Trailer that Housed Truman Capote

Just a short walk from Sloppy Joe’s down Duval Street, you’ll find the waterfront view so irresistible, Truman Capote begged for it. When Capote was looking for a place to stay for a winter, he ended on the doorstep of Key West native David Wolkowsky. While trying to find suitable accommodations for Capote, Wolkowsky invited Capote to his bamboo-covered double-wide trailer that stood 10 feet from the waterfront, Wolkowsky’s temporary residence. Capote begged for the use of the luxury trailer upon seeing it. Wolkowsky finally relented, and Capote spent the winter holed up writing there, only to emerge with the manuscript for his novel Answered Prayers.

Tennessee Williams’s Backyard Asylum

After a brief stint in a Key West boarding house, Tennessee Williams bought a metal-roofed, red-shuttered cottage at 1431 Duncan Street in 1949, where he would spend the rest of his life. Williams went on to transform the property into a compound that included a guest house, a swimming pool, and a one-room writing studio that he called the “Mad House.” The author’s home and his backyard studio achieved a certain amount of notoriety in the late 1970s when the home was repeatedly broken into and his eccentric gardener was found murdered in the backyard. Widely attributed to anti-gay sentiments of the era, Williams reacted to the violence by saying, “I’ve been here longer than they have, and I’m not leaving.”
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