Key West isn’t just a drinking town—though, let’s be honest, they do that pretty well. But this small island has another side, one filled with stories, poetry, and some of the most famous authors to ever put pen to paper.

If you love books and literature, this is your paradise. Hemingway wrote here. Tennessee Williams swam here. Robert Frost reflected under the palm trees here. Even Judy Blume still calls this island city home.

For those of you in the Fun in Key West Book Club, or our VIP Chapters & Cocktails Crew, today’s post is for you. We’re exploring why Key West is truly the best place for book lovers, how the island continues to inspire American writers, and what you can experience on your own literary adventure.

The Island of Inspiration

There’s just something about Key West that gets under a writer’s skin. Maybe it’s the sound of the waves rolling in, the scent of coconut palms, or the way time seems to melt away. From the moment you cross the Overseas Highway and step into this island’s slower rhythm, you understand why so many creative souls called it home.

Key West has always been a sanctuary—a place to escape deadlines, expectations, and even winter. Every corner has a story, and if you listen closely, the wind through the palm fronds sounds suspiciously like the clack of typewriter keys.

The Legends Who Lived Here

Key West’s literary history reads like a who’s who of American literature. The island’s unique charm and relative seclusion provided the perfect backdrop for some of the greatest minds to create their most famous works.

Ernest Hemingway – The Old Man of Whitehead Street

Let’s start with the island’s most famous resident: Ernest Miller Hemingway. The Nobel Prize-winning author and Pulitzer Prize recipient made his Key West estate on Whitehead Street world-famous. He arrived in 1928 with his second wife, Pauline Pfeiffer, after her wealthy uncle gave them a stunning Spanish Colonial home as a wedding gift. It was Hemingway’s first real house, complete with lush gardens and tamarind trees, and it became the heart of his creative life.

Here, he wrote or worked on Green Hills of Africa, The Snows of Kilimanjaro, and For Whom the Bell Tolls. His stories were often inspired by his love of deep-sea fishing, travel, and adventure. His writing studio, perched above the carriage house, still looks as though he might stroll in with a glass of rum and start another masterpiece.

When he wasn’t writing, he was at Sloppy Joe’s Bar on Greene Street, swapping stories with his good friend Joe Russell, a local ship’s captain and rumored bootlegger. Their friendship inspired more than a few tales in his famous books.

Hemingway was also a notorious cat lover. He was gifted a snow-white polydactyl cat named Snow White, starting a colony of cats with extra toes that still live on the property today. These Hemingway cats—descendants of Hemingway’s original—have become almost as famous as the writer himself.

Visitors can tour the Ernest Hemingway Home and Museum, now a National Historic Landmark, and see the famous swimming pool Pauline built while Hemingway was covering the Spanish Civil War with his third wife, Martha Gellhorn. Legend has it, he threw a penny into the wet concrete, declaring it his “last cent.” Each July, the island celebrates Hemingway Days with a Hemingway look-alike contest, a marlin tournament, and writing competitions.

Tennessee Williams – The Poet of Duncan Street

Just a few blocks off Duval Street, you’ll find 1431 Duncan Street, the tranquil Key West home of playwright Tennessee Williams. He first arrived in 1941 and quickly found sanctuary on the small island. The Pulitzer Prize-winning playwright, known for A Streetcar Named Desire and The Rose Tattoo, found a sense of peace in Key West that shines through in his writing.

He loved to write in the mornings and swim in the afternoons, finding balance under the coconut palms. His two-story house with its lush gardens and red shutters was his haven for decades. A fun local legend says Williams was baptized at St. Mary’s Star of the Sea while quite intoxicated. Today, the Tennessee Williams Museum on Truman Avenue celebrates his famous works and his enduring connection to the island city. Each March, Key West honors him with a month of performances and readings.

Robert Frost – The Poet Behind the Palm Trees

If you thought the Florida Keys were only for cocktails and sunsets, meet Robert Frost. America’s poet laureate began visiting in 1934, spending nearly 16 winters in a small cottage behind Jessie Porter’s home on Caroline Street. Known as the Robert Frost Cottage, it was a serene hideaway where he reflected and wrote. Frost often called Key West his “place to breathe,” entertaining other famous people like John Hersey, Richard Wilbur, and Shel Silverstein.

Other Literary Greats Who Loved the Island

• Elizabeth Bishop: The poet lived on White Street and Elizabeth Street, crafting poetry that captured the rhythms of the sea.
• Shel Silverstein: The beloved author wrote children’s classics and adult humor while living on William Street.
• Jimmy Buffett: He lived and recorded music here, turning storytelling into song. His first Key West apartment was right next to Louie’s Backyard.
• Judy Blume: The queen of coming-of-age stories now lives here and runs Books & Books, a locally owned gift shop and bookstore.

From Hemingway’s six-toed cats to Tennessee Williams’ red shutters, this island city has always been a magnet for dreamers. It proves that even the wildest spirits can find peace in paradise.

Literary Landmarks & Festivals to Visit

If you’re planning a visit, here are some must-see stops for any book lover.

Landmarks:

• Ernest Hemingway Home & Museum (Whitehead Street): Tour the home, meet the Hemingway cats, and see the famous writing studio.
• Tennessee Williams Museum (Truman Avenue): A beautiful tribute to one of America’s greatest playwrights.
• Robert Frost Cottage (Caroline Street): Though usually closed to the public, it’s worth walking by this historic spot.
• Casa Antigua (Simonton Street): The first place Hemingway stayed on the island, now an escape room with tropical gardens.
• Books & Books (off Duval Street): Judy Blume’s charming bookstore, which often hosts readings and signings.

Festivals:

• Hemingway Days (July): Features a Hemingway look-alike contest, marlin fishing tournament, and literary readings.
• Tennessee Williams Month (March): A month of plays, art, and events celebrating his own work.
• Key West Literary Seminar (January): Writers, poets, and readers from all over the United States gather to share inspiration.

Today’s Storytellers

That creative spark from Hemingway’s time still burns bright. It’s the same spirit that fuels our Fun in Key West Book Club, where we read novels set in paradise and connect with authors.

For those who crave more, our VIP Chapters & Cocktails Club takes it to another level. You get a digital magazine with playlists, trivia, and cocktail recipes. Plus, you can join live author chats and get insider access to interviews. It’s like your own mini Hemingway Days, but with fewer marlins and more margaritas.

Your Next Chapter Awaits

Key West might be known for its nightlife, but it’s truly a sanctuary for storytellers. Every street—from Whitehead Street to Duval Street—holds the echoes of famous works, creative minds, and maybe a few good bar brawls.

Whether you’re planning a short trip down the Overseas Highway or just need an escape through books, Key West’s literary history will make you fall in love.

In Key West, every story ends with a sunset… and maybe a cocktail.