Sunset Key Cottages, a Luxury Collection Resort, Key West

4.2 (70 reviews)

245 Front Street, Key West, FL, 33040, United States   •  Weather:    •   Local Time:     •  Phone: 305-292-5300   •  Hotel Reservations: 866-837-4249


Literary Characters of Key West

Although Ernest Hemingway’s name is most often associated with Key West’s literary history, the island’s rich culture is wide and deep and includes Tennessee Williams, Robert Frost and numerous contemporary writers.


Ernest Hemingway

Hemingway lived in Key West during the 1930s and 1940s. His legacy lives on most visibly at the home he owned in Old Town, which since 1964 has been open to the public as the Ernest Hemingway Home & Museum. He spent his mornings writing some of his most notable works, including A Farewell to Arms, in his quaint second-story writing studio, where his manual Royal typewriter is on display. In the afternoons, he went fishing and enjoyed socializing at his favorite watering holes, including the original Sloppy Joe’s.

The home is still furnished as it was when Hemingway and his family lived there, including chandeliers they bought in Paris. The lush grounds, historic pool (the first swimming pool built in Key West) and resident six-toed cats round out the museum experience. Hemingway’s first residence in Key West, Casa Antigua (above a former car dealership and behind the Pelican Poop Shoppe) is a hidden gem that provides a glimpse into Hemingway’s early life on the island.

To commemorate the author’s birthday, the annual Hemingway Days are held in July. Events include readings, art exhibits, a marlin fishing tournament and a contest for stocky white-bearded men resembling “Papa” Hemingway.

Poets and Others

Legendary poet laureate Robert Frost also spent time in Key West, wintering in a garden cottage at 410 Caroline Street from 1945 to 1960. Although the cottage is no longer open to the public, it’s a fine example of Key West conch architecture. Every spring, the Studios of Key West, a local arts community, hosts the Robert Frost Poetry Festival, which features poetry and haiku workshops and readings.

As further evidence of the island’s lively literary heritage, best-selling contemporary authors and other writers converge on Key West every January for the Key West Literary Seminar. The five-day event includes a variety of writing workshops and has featured such luminaries as Margaret Atwood, Joyce Carol Oates, Gore Vidal, Ian McEwen and Amy Tan. One year, seven U.S. poet laureates took part in events all over town.


Tennessee Williams

For playwright Tennessee Williams, Key West provided the ideal hideaway to escape from his celebrity. He spent time on the island living virtually unnoticed in a small cottage at 1431 Duncan Street, mainly keeping to himself. He bought the residence in the 1940s and owned it until his death in 1983. It’s believed that he wrote the first drafts of A Streetcar Named Desire in Key West.

The playwright’s legacy is immortalized in Key West’s most recognized theater, the Tennessee Williams Theater on College Road. Located on the campus of Florida Keys Community College, the venue is the site of locally produced and traveling stage productions, as well as concerts by local music groups.