Sunshine and the Creative Mind: 10 Ways to Find Inspiration in Key West

“I work everywhere, but I work best here.”
– Tennessee Williams (of his time in Key West)

Something mysterious happens to writers when they visit Key West. They tend to fall in love with the place and never want to leave.

Take novelist Ernest Hemingway. He and his wife, Pauline, arrived on an ocean liner from Paris, by way of Cuba, in 1928. As the story goes, they had been planning to pick up a new car they’d ordered and drive North. But when the car was delayed for several weeks, stranding them in paradise, they rented a room at the Trev-Mor Hotel and soon fell captive to the island’s charms, making Key West their home for over a decade. Eventually they purchased their famous Spanish Colonial style house on Whitehead Street, where Hemingway wrote A Farewell to Arms, Death in the Afternoon, and Winner Takes Nothing, among others.

Playwright Tennessee Williams first vacationed in Key West in 1941, often staying at La Concha Hotel, where he finished writing A Streetcar Named Desire. Eight years later, he purchased a home on Duncan Street and created a writing studio he named “the Mad House,” where he wrote and painted until his death in 1983.

Singer, songwriter, and author Jimmy Buffett first arrived in Key West in 1971 to heal a broken heart caused by the end of his first marriage and the rejection he’d encountered in Nashville. He remained a resident for 30 years, during which time he found his tropical sound and wrote the lyrics to the song that catapulted his career, “Margaritaville,” as well as three best-selling books.

Novelist Judy Blume first arrived in Key West in the mid-1990s to escape the harsh New York City winter and finish her adult novel, Summer Sisters. She and her husband fell in love with the island and made it their home for the next 25 years. Novelist Meg Cabot and her husband share a similar Manhattan-to-Key-West story, becoming residents in 2005, where she has continued penning The Princess Diaries series as well as children’s novels, young adult novels, a manga series, and more.

With warm winters, palm-tree-lined streets, and electric blue water, it’s easy to understand what attracts writers to Key West. But what compels them to stay?

Maybe it’s the opportunity to live a simpler life—one where you can start your morning with a walk on the beach, like Robert Frost, who wintered in Key West from 1945-1960, where you can catch your dinner, like Hemingway, who spent his free time fishing, and where you can travel anywhere you need to go by bicycle. Perhaps it’s the uplifting effect of near-constant sunshine on the melancholic creative mind. Or maybe it’s as simple as Tennessee Williams once put it, “it’s the only place in this country where it’s warm enough to swim every day of the year.”

Spend a little time in Key West, and you too may begin to feel its seductive pull for once you look past its obvious paradisal patina, you’ll find interesting people, tales of triumph and defeat, and an enchanting history that’s often stranger than the fiction written there.

Whether you have three days or three decades to explore, Key West is the perfect place to slow down, engage your senses, and rekindle your creativity. So, grab your journal and follow me on an inspiration field trip to Key West.

Here’s your idea-generating itinerary:

1. Awaken your inner artist at Books & Books.

Sometimes sheer proximity to creative energy is enough to spark inspiration. That’s why a visit to Books & Books must be among your first stops in Key West. This isn’t just any independent bookstore, it was founded by the writer who shaped a generation of readers, Judy Blume, and her husband, nonfiction writer George Cooper, in 2016. Located at The Studios of Key West, a former Masonic Temple turned cultural hub, artistic entertainment is on tap multiple nights a week with author events, concerts, and performances. (Also, there’s a chance you might bump into Judy, and what’s more inspiring than that?)

2. Craft memorable characters in Mallory Square.

The golden hour before sunset is a magnetic force that attracts tourists, local artisans, and buskers to the water’s edge in Mallory Square, where the crowd bursts into applause when the sun finally dips beyond the blue horizon. On any given night, you’re as likely to see a talented teen playing guitar for college money as you are a fire-breathing man balancing on a pyramid of precariously stacked chairs.

Creative challenge: Find a bench and observe the cast of characters that meander by. Observe the qualities, mannerisms, and details that capture your attention. How might similar traits breathe new life into your characters?

3. Develop dialogue on Duval.

Many writers admit that some of their best dialogue is inspired by talking to (or eavesdropping on) strangers. When the sun goes down in Key West, there are few better places to do both than Duval Street, which has been called “the Bourbon Street of Key West.”

Interesting conversations are always on tap at the Chart Room at the Pier House Resort, at 1 Duval, where Jimmy Buffett got his start playing for drinks. La Concha Hotel, at 430 Duval, was popular among literary legends, like Tennessee Williams, and other famous figures. And, of course, Ernest Hemingway’s favorite watering hole was Sloppy Joe’s, which was also enjoyed by Truman Capote and Shel Silverstein. Visit its current location at 201 Duval and its original location at 428 Greene Street, which now houses Captain Tony’s Saloon. For especially interesting eavesdropping, stop by Sloppy Joe’s on July 21 to celebrate Hemingway’s birthday and watch hundreds of “Papa” doppelgängers compete in a three-day Hemingway Look-Alike Contest.

Creative challenge: Observe what people are talking about. What unique words or phrases do they use? How do their gestures and expressions accentuate their words? Consider how these details might create a unique voice or viewpoint for your characters. 

4. Curate conflict at the Key West Lighthouse.

If your story lacks conflict, you may find inspiration at the Key West Lighthouse on Whitehead Street. Here you’ll learn about the extraordinary life and perseverance of Barbara Mabrity, whose husband Michael was appointed as the lighthouse keeper in 1826. When he died of yellow fever six years later, Barbara took over his post, keeping the light lit under constant threats of war and weather while raising six young children. And when a Category 5 hurricane struck in 1846, toppled the lighthouse, and destroyed everything she owned, she continued serving as a lighthouse keeper on Key West until she was 82 years old.

Creative challenge: Brainstorm all the ways your setting can make life challenging for your characters.

5. Binge on backstory at the Shipwreck Historeum.

Key West’s inviting blue water might be the hook that pulls us into its tropical tale, but you’ll need to look beneath the surface—literally—to get the island’s full story. Once you do, you’ll learn the Florida Reef has made these tranquil waters among the most treacherous in the world for sailors. Visit the Shipwreck Historeum to learn about the golden age of sail, which saw at least one wreck per week and lured treasure hunters to its shores to salvage and auction off goods from sunken vessels—a pursuit that once made Key West one of the richest cities in America.

Creative challenge: As you unearth these tales of tragedy and triumph, consider which elements of your story are not what they seem. How might you leverage unexpected backstory to lure readers deeper into your story world?

6. Hook it like Hemingway.

We writers know that sometimes the best writing happens when you’re not writing at all. When Hemingway wasn’t writing, he spent much of his free time aboard his 38-foot wooden fishing boat, Pilar. These adventures are said to have inspired The Old Man and The Sea and Islands in the Stream. Not surprisingly, Key West is one of the best deep sea fishing destinations in the country. Hire a guide to show you the most productive fishing spots and teach you the proper technique to land marlin, mahi mahi, and tuna.

Creative challenge: As you soak in the solitude waiting for the big one to bite, pay attention to the places your mind wanders, for it’s moment like this, when we’re miles away from pen and paper, that we often hook our best ideas.

7. Pedal and ponder on the Florida Keys Overseas Heritage Trail.

In the late 1800s, Henry Flagler envisioned a single railroad system would connect Florida’s east coast, from Jacksonville to Key West. By 1912, he’d made the Florida East Coast Railway’s Over-Sea Railroad to Key West a reality. Eventually, the growing popularity of automobile travel followed by the Labor Day Hurricane of 1935, which heavily damaged the railway, led to its demise. The state purchased the land and bridges and repurposed the route for vehicle traffic, creating the Overseas Highway.

Today, the Florida Keys Overseas Heritage Trail (FKOHT), a 90-mile paved recreation trail that follows the former railbed, runs alongside it. Eventually, it will cover 106 miles, preserving all 23 of Flagler’s remaining bridges. FKOHT starts (or ends) in Key West. Pick it up at Higgs Beach or Bayview Park, and ride over the ocean and through the Lower Keys, stopping to refuel at Baby’s Coffee (at mile marker 15).

Creative challenge: As you pedal, ponder the forces of change at work in your story. What do your characters dream of building or achieving? What headwinds do they face? What’s relevant now that might become obsolete (or disrupted) in the near future?

8. Spark your imagination on a deserted island.

Seventy miles west of Key West, in the middle of the Gulf of Mexico, is Dry Tortugas National Park. Accessible by private boat, high-speed ferry, or sea plane, 99% of the park is underwater, protecting the largest concentration of shipwrecks in North America. The main island, Garden Key, is home to Fort Jefferson, a massive coastal fortress that began construction in 1846, required 16 million bricks, and technically still isn’t complete.

An impressive feat of human ingenuity (and patience), Fort Jefferson was built to protect one of the most strategic deep-water anchorages in North America, and it’s had many lives over the years. During and after the Civil War, it served as a prison for criminals and deserters, and being sentenced there was considered a fate worse than death. Eventually, it became a quarantine station for the Marine-Hospital Service, then a seaplane base during World War I, and finally an observation post during World War II before being declared as a National Park in 1935.

Creative challenge: As you explore Fort Jefferson, imagine what life might be like in a place cut off from civilization, modern conveniences, and essentials, like fresh water. Consider the challenges your characters face and what “survival” means to them.

9. Follow in the footsteps of literary legends.

There’s something almost magical about standing in the same place your favorite writer once stood, inhabiting the same space as greatness. It’s not hard to do this in Key West, since so many literary legends, including 12 Pulitzer Prize winners, have called the island home at one time or another.

To get the inside scoop on where Tennessee Williams, Shel Silverstein, Elizabeth Bishop, Robert Frost, and other famous writers lived, worked, and played, take the Old Town Literary Walking Tour ($30/person)—a 90-minute narrated tour that departs from the Monroe County Public Library every Friday at 5 p.m. and Sundays at 10 a.m.

Creative challenge: As you learn about each writer’s interests and work, consider how one place can inspire such a variety of creative expression. What does it inspire in you?

10. Study with today’s greats.

If you happen to be in Key West in mid-January, don’t miss the Key West Literary Seminar, a four-day event that explores a unique literary theme with presentations by accomplished writers. There’s also a Writer’s Workshop Program for writers at all stages to explore the craft and experiment with new techniques.

And if you have an extra $1,500 lying around, you can take all the inspiration you’ve gathered during your time in Key West and book a three-hour evening writing session at the Hemingway Home, where you and a guest will have full access to Hemingway’s house, gardens, and writing studio to work on your next masterpiece in the same place he created his.

 

Have you been to Key West? If so, where did you find inspiration?

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