Long before the overseas highway connected it to the mainland and cruise ships made it a regular port of call, Key West was a tropical frontier town. Populated in the early twentieth century by an eclectic mix of fishermen, spongers, rum runners, and cigar makers, the tiny island was more Caribbean than American. Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill, with its remote location, tropical setting, and wild spirit

Tennessee Williams first came to Key West at age thirty, in 1941. After living in a boarding house, he bought a clapboard Bahamian cottage on the outside of town, at 1431 Duncan Street, where he created a compound with a guest cottage, swimming pool, and one-room writing studio he called the “Mad House.” Williams was baptized, with encouragement from his brother and a fair amount of alcohol, at St. Mary Star of the Sea Catholic Church on Truman Avenue.

Among the writers and artists that Williams met while living in Key West was Elizabeth Bishop. She came to the island in the 1930s and initially rented an apartment at 529 Whitehead Street. In 1938, she purchased a nineteenth century clapboard Eyebrow house at 624 White Street, where she lived until 1946. She later lived in an apartment at 611 Frances Street, which looked out across tin shanty roofs and palm trees.

In a letter to Marianne Moore, Bishop describes her surroundings: “I have one Key West story that I must tell you. It is more like the place than anything I can think of. The other day I went to the china closet to get a little white bowl to put some flowers in and when I was rinsing it I noticed some little black specks. I said to Mrs. Almyda, ‘I think we must have mice’ – but she took the bowl over to the light and studied it and after a while she said, ‘No, them’s lizard.'"

Near Solares Hill, the island’s highest point at sixteen feet above sea level, is Windsor Lane Compound, established in 1976. The assortment of restored shacks, shanties, and cottages, were once winter homes for writers such as Richard Wilbur, John Ciardi, John Hersey, and Ralph Ellison. On William Street is a Greek Revival house and writing studio once owned by Shel Silverstein.

At 410 Caroline Street is Heritage House Museum, once the home of Jessie Porter, a fifth-generation “conch," or Key Wester. Originally built in 1830, Porter purchased the run-down Colonial home in 1930 and lovingly restored it. Her exotic garden became the center of Key West society, and artists and writers frequently gathered there, including Wallace Stevens, Archibald MacLeish, and Thornton Wilder. An old friend of Porter, Robert Frost spent many winters in her garden cottage.

Another frequent visitor, Wallace Stevens once wrote in a letter that Key West “is the real thing... the sweetest doing nothing contrived.” Though good friends with Hemingway, one rainy night outside of Sloppy Joe’s bar, the two got into an infamous brawl in which Stevens broke his hand on Hemingway’s jaw. The island also inspired Stevens’s evocative poem “The Idea of Order at Key West” which includes the lines:

Why, when the singing ended and we turned
Toward the town, tell why the glassy lights,
The lights in the fishing boats at anchor there,
As night descended, tilting in the air,
Mastered the night and portioned out the sea,
Fixing emblazoned zones and fiery poles,
Arranging, deepening, enchanting night.