The history of Key West has been marked by the comings and goings of many literary greats, from Ernest Hemingway to Judy Blume. Here’s how you can walk in their footsteps…beyond just a visit to The Hemingway House on Whitehead Street.

Key West’s history has featured many cameos from literary heavyweights, including author Ernest Hemingway and playwright Tennessee Williams, both who not just lived here but also penned famous works in the southernmost island city. So if you’re looking to relive some of the spaces and places that have been touched by these literary legends, first, make your headquarters at The Laureate Key West – the all-suite retreat that is an ode to the laid-back lifestyle that inspired these authors’ great works of literature, music, and poetry. Once you get settled in, set your watch to island time and venture out to these must-see literary landmarks.

“Once There was a Tree”


The inspiration for Shel Silverstein’s famed children’s book The Giving Tree, written in 1964, was actually a local massive banyan tree that sat outside his wooden two-story Key West home on William Street. Unfortunately, in 2017, Hurricane Irma uprooted the tree, sending it toppling over the century-old home. But, the site is still worth a visit: the historic property – albeit in a bit of disarray – remains with the tree beside it, demonstrating not just the gravitas of the literary history here, but the natural history, too.

The House on Duncan Street

Made infamous by a series of break-ins in the 1970s, 1431 Duncan Street was formerly home to the famed playwright, Tennessee Williams. In 1949, he purchased the modest metal-roofed, red-shuttered cottage and transformed it into an elaborate compound that included a guest house and a one-room writing studio that he called the “Mad House.”

Hemingway’s Haunt


The iteration of Sloppy Joe’s that Hemingway used to frequent, image circa 1950 from the Monroe County Library Collection.

Everyone knows about the Hemingway Home on Whitehead Street, the former residence of Ernest Hemingway, where he lived between the years of 1931 and 1939 and wrote 70 percent of his lifetime works. If looking to feel Hemingway’s energy in a not-so-obvious tourist attraction, however, head over to Sloppy Joe’s to quench your thirst and hit a historic hotspot. The story goes that Ernest Hemingway would frequent the watering hole in the 1930s with an eccentric cast of local characters by his side. So pull up a stool, order a cold one, and see if you rub elbows with any literary ghosts.

A Temple to Literature

Pay a visit to the former 1950s Masonic Temple-turned-bookstore at the corner of Simonton and Eaton streets, owned by none other than the young adults’ novelist Judy Blume. Much more than just a bookstore though overseen by the author best known for her book Are You There, God? It’s Me, Margaret, Books & Books at The Studios of Key West is a nonprofit with a wealth of books, classes, studio space, and live performances. Spend an afternoon browsing the books or catch one of their art exhibits!


Where to Stay The Laureate Key West | Opal Key Resort & Marina | The Capitana Key West | Sunset Key Cottages