Key West: A Writer’s Paradise

Ernest Hemingway Key West
Island Genn posing next to a sculpture of Ernest Hemingway in Key West, FL

Ernest Hemingway‘s name is synonymous with Key West. He may be our most well known writer ever to have called the island home, but there are plenty of other that have or still do call Key West home. Names like Tennessee Williams, Robert Frost, John Hersey, James Merrill, Elizabeth Bishop, Richard Wilbur, John Malcolm Brinnin, Alison Lurie, Robert Stone, Thomas McGuane, Jim Harrison, Philip Burton, Judy Blume, Nancy Friday, Harry Mathews, Marie Chaix, Shel Silverstein, Wilfrid Sheed, David Kaufelt, Ann Beattie, Jimmy Buffett and Philip Caputo, among others. While some houses are open to the public, most are now privately owned by normal folks, so please do not go knocking on their doors for a tour!!!

When Hemingway first arrived in Key West with his second wife, Pauline, back in 1928, he stayed at what is now known as Casa Antigua located on Simonton Street. The building is currently a gift shop offering tours of their gardens. After renting several apartments, the Hemingway’s finally found their perfect home and purchased the Spanish Colonial at 907 Whitehead Street which had been built by famed Key West wrecker Asa Tift. Other famous Hemingway haunts include Sloppy Joe’s Bar, originally located at 428 Greene Street, now the home of Captain Tony’s Saloon. And of course, the well know restaurant, Blue Heaven on Petronia Street was once the boxing ring Hemingway had to move from his yard once he built his pool. Each July, locals celebrate Hemingway’s life in Key West with the Hemingway Days Celebration which includes events such as a Hemingway look-a-like contest, arm wrestling competitions, a Marlin Fishing Tournament, and a writing competition directed by Hemingway’s granddaughter Lorian.

 In 1941 Tennessee Williams began visiting the island. And in 1949 he purchased a home at 1431 Duncan Street in which he resided in for the rest of his days. The house is now privately owned and not opened to the public, but it is a standout with its red shutters. The acclaimed playwright’s “The Rose Tattoo” was turned into a film and shot in Key West in 1956. And in 1980, The Florida Keys Community College opened a theater and named it after their most famous play writing resident. The College is located at 5901 College Road on Stock Island, and plays host to many concerts and plays. Williams was also baptized a Catholic at St. Mary’s Star of the Sea located on Truman Avenue.

 In 1934, Robert Frost first visited Key West, and he visited each winter from 1945 to 1960. There was a small cottage behind the home of local resident Jessie Porter that Frost would stay at, and hence the cottage has been dubbed the Robert Frost Cottage. Until recently the home located at 410 Caroline Street was open to the public for tours. Frost served as the poet laureate of the United States from 1958 to 1959, and he happens to be the poet that penned my favorite poem of all time, “The Road Not Taken”. I was lucky enough to tour the home once long ago; unfortunately, I did not get any photos.

Jesse Porter also hosted several other artists and writers at her home including Wallace Stevens, Archibald MacLeish, and Thornton Wilder.

Other notable authors include James Leo Herlihy who penned Midnight Cowboy and once owned a small house located on 709 Baker’s Lane and Tom McGuane, author of Ninety-two in the Shade, who resided at 123-125 Ann Street, 1011 Von Phister Street, and 416 Elizabeth Street. Both of these novels were turned into Hollywood films.

Elizabeth Bishop, a Pulitzer Prize winning poet lived at 624 White Street from 1938 to 1946. But before she purchased her home, Elizabeth first rented an apartment at 529 Whitehead Street in the 1930’s. After she sold her house she lived for a short time in an apartment located at 611 Frances Street.

And another Pulitzer Prize winning poet, James Merrill, lived at 702 Elizabeth Street. Funny that Elizabeth Bishop didn’t live on Elizabeth Street.

Philip Caputo, an author and journalist, lived at 1101 Casa Marina Court and frequented the now closed Full Moon Saloon.

The Windsor Lane Compound of houses near Solares Hill, which is the highest point of the island, was once home to Pulitzer Prize winning poet Richard Wilbur, as well as famous authors John Hersey, John Ciardi, and Ralph Ellison.

On William Street is the once time house and writing studio of Shel Silverstein. Look for the Greek revival style of architecture to locate which house was his.

The Casa Marina Resort located on Reynolds Street and the La Concha Crowne Plaza located on Duval Street are both popular hotels that many writers including Tennessee Williams, Robert Frost, and Wallace Stevens have stayed.

And who hasn’t heard of Margaritaville? Jimmy Buffet’s store and restaurant is located at 500 Duval Street. The songwriter once lived in a house on Waddell Street, right next to Louie’s Backyard as well as several other houses on the island. And his one time recording studio is located at the Historic Seaport. 

Famed kids author Judy Blume who wrote one of my favorite childhood books, Freckle Juice, currently owns a house in Key West on Flagler Avenue.

Every winter in January, writers flock to the island for the annual Literary Seminar.  Workshops are given by notable authors to prospective writers as well as avid readers. The theme changes yearly, with the theme for 2014 being “The Dark Side”.

If you plan on visiting the island yourself, maybe you will find the inspiration to write too.

To see what is happening on the island during your visit, check out our Key West Events Calendar to see other upcoming special events. For more information about the fun side of Key West… things to do and see in our island city, go to our Key West Web Site.

Before deciding where you are going to eat while visiting Key West or any of the Florida Keys, be sure to read my  restaurant reviews; check out our restaurant review section of this blog.

Feel free to Email Me if you have any questions about Key West!!


Island Genn – Your Key West Concierge

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