Take an Ernest Hemingway-Inspired Trip to Key West
A lifelong love of the literary giant leads to the backroads, bars, and boats of Key West, Florida.
In the early winter of that year I rented a flat in a town that looked across the sea and the Gulf Stream to Cuba. In the front yard of the flat there were palmettos and palms, tall and thin in the sun, and the shade was cool and quiet and lovely in the heat. Bikes went by the house and down the road and the riders' voices stirred the leaves on the trees. There were chickens in the road and small white lights on the fence and the bikes scattered the chickens not to mention the cats.
You will start writing like this (and thinking like this and even dreaming without commas), I discovered, rereading Hemingway in Key West. It's a lovely experiment. Hemingway says things are lovely a lot, and they are. "It's the best place I've been any time, anywhere," he wrote of the Florida island. "Flowers, tamarind trees, guava trees, coconut palms … Got tight last night on absinthe and did knife tricks."
Lured by the myth of the man, I packed up The Old Man and the Sea and took a sort of reverse literary pilgrimage from my home near Ketchum, Idaho (where Papa spent his final days), to the southernmost tip of the continental United States, where he lived from 1928 to 1939. Like legions of writers before me, I packed books, notebooks and pens, shorts … but mostly books. Seeking traces of the colossal writer, I rented a cottage with a 1930s vibe, including lazy ceiling fans and a vintage 1939 palm garden framing mustard yellow shutters. After I traded snow boots for flip-flops and had some coffee at the table in the garden while turning pages that felt like old friends, I remembered why I've always loved Hemingway.
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Hemingway wrote all or part of five books, a play, and two of his most famous short stories in Key West. It was also here that he forged his macho image: fishing, drinking, carousing. What is it about this laid-back subtropical town? I wonder, happily walking the few short blocks from my cottage to Salute! On the Beach, a funky shack alleged to be a writer's hangout. I don't see any writers (at least none I recognize), just boisterous lunchgoers at open-air tables drinking mojitos. The view looks straight to Cuba, 90 miles across the Straits of Florida, and sitting here it's easy to envision Papa fishing aboard his beloved Pilar or, later, writing at his desk at Finca Vigía, the home he built outside Havana when Key West grew too crowded for him.
Talk to anyone who lives here and they'll tell you there's no Hemingway left, that it's all tourist bunk—the annual Hemingway Days fest, with barrel-chested, white-bearded men competing in a campy lookalike contest; a zany "running of the bulls;" and a fishing tournament when anglers can, according to organizers, "emulate Papa's devotion to deep-sea fishing."
But if you're a writer, what remains in Key West isn't about that. Not even remotely. It's about the words and an openness, and that this place is still a little twisted, even if it is a lot spiffier than it used to be. For Hemingway, the words were always connected to place, and if you pay attention, you'll find that indolent, adventurous spirit still very much in the air.
In the late afternoon, I take a stroll to Hemingway's former home, a stately Spanish Colonial that's now a museum. Stepping through the iron gates, I'm stunned by the crowds and the enduring global curiosity about Hemingway. (The guy in the gift shop tells me they get more than 1,000 visitors a day.)
"Hemingway's second wife, Pauline, was a very stylish woman!" says our tour guide, stopping to point out the chic chandeliers, Art Deco tiles, and portraits of Hemingway's four wives. Pauline was a journalist at Paris Vogue when she and the young novelist (then married to Hadley) met.
"Hemingway was very naughty," she says. We learn, among other things, that he met Martha Gellhorn (wife No. 3) in the Key West bar that was then Sloppy Joe's but is now Captain Tony's, and moved with her to Cuba, where Mary Welsh (wife No. 4) was a foreign correspondent. He moved with Welsh to Ketchum.
It's easy to be charmed by the dozens of polydactyl cats who roam the leafy grounds and are said to be descendants of Hemingway's six-toed cat Snow White. But the real highlight is his writing studio. Here, at a simple wooden table surrounded by shelves lined with books, sits the original Royal Portable typewriter on which he wrote Death in the Afternoon, The Green Hills of Africa, To Have and Have Not, and the famed short story "The Short Happy Life of Francis Macomber."
This is sacred ground. But it's shocking too, the stillness. Look past the cats, the drinking, the fishing, and the womanizing, and writing is a solitary act. I take pictures of the space. "Good thing Hemingway isn't trying to work here now!" someone says as we both snap an Instagram of a cat.
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"You know, I originally moved to Key West 36 years ago because I'd read The Old Man and the Sea," Capt. Roc says when I phone to book a day of offshore fishing with Key West Pro Guides. "The giant marlin fishing was in Cuba, and Hemingway wrote that book in Cuba, but it was always in the back of my head."
Waking up at 6 a.m. the next day to make it to the marina by 7:45, I wonder what on Earth I was thinking. Hemingway, after all, was famously disciplined, writing every day at dawn. But once I meet Capt. Dave, an easygoing fifth-generation Floridian, and speed across the shimmering blue water in his fiberglass Conch 27, I'm glad to be on the sea. "It keeps you humble," Capt. Dave says when we get skunked catching baitfish.
Finally, after driving around in light chop for a while, Dave says, "We're in the bait!" and boats 10 speedos (otherwise known as redtail scad) in a flash. I keep hooking something called a blue runner, a worthless fish with a ferocious hunger that fights like hell. "Let's see if we can catch us a WAHOO!" Dave exclaims once we've stockpiled enough bait, threading live speedos on big hooks. When one of the two rods starts jumping and bending, we know I'm no match, so Capt. Dave reels in a gleaming, 4-foot king mackerel—then another, and another. "They're toothy," he says, removing hooks from jaws packed with teeth like razorblades. "Careful!"
Even though I catch nothing but blue runners, it's wonderful on this water, pale blue like the sky, and I leave with a whole new level of respect for the giant marlin Hemingway fought.
Famished the next morning after my day at sea, I hightail it toward Pepe's, a local institution since 1909. It's a sparkling day, with roosters crowing and sun bouncing off the streets. An anything-goes atmosphere pervades: the crazy feral chickens, the irreverent gay scene, an expansive ease. Key West, I decide, feels as wildly exuberant and tolerant as the foliage.
The waitress at Pepe's calls me "hon" and tucks me into a varnished-pine booth as snug as the cabin of Hemingway's boat. The coffee comes in a thick white mug, and the bill for it—plus eggs, bacon, home fries, homemade banana-walnut bread, and juice—totals $16.98. Seeing as it's noon, and I'm on Hemingway time, I decide I'd better check out Captain Tony's, where Hemingway went to drink his scotch-and-sodas. Greene Street, once a ramshackle lane, is full of milling tourists in T-shirts. The drinking here starts early.
At Tony's, I settle onto a stool and order a beer. A guitarist croons "Sweet Home Alabama" beneath forests of dollar bills tacked to the rafters. The guy sitting next to me strikes up a conversation.
I'm meeting a guy at a bar! I think, astonished because I haven't been bar-hopping by myself in about 30 years.
I tell him I'm a writer, and he says, "My 14-year-old daughter wants to be a writer! Can you believe she asked for bookshelves for Christmas?"
He pulls out his iPhone and shows me a video of his child hopping around stacks of books arranged by genre on her bedroom floor. He is going on and on about her when it hits me: I'm just a mom in a bar now, but the beer tastes cool and clean.
It feels like a Hemingway moment to me.
The Best of Key West
Get schooled on our favorite things to do in Florida's southernmost point.
The quickest way to Key West is by air to Key West International Airport. To build anticipation, consider flying to Miami and driving three hours south along U.S. 1, which becomes the breath-taking Overseas Highway.
Vacation Homes of Key West offers a wealth of historic cottages that channel the atmosphere of Hemingway and his generation, including Butterfly Garden, the base for this adventure, with its own garden planted in the 1930s.
Key West Pro Guides can help even a fishing novice get the Hemingway experience on the water, and they're ready to help experts land that trophy fish.
Don't miss dinner at this one-time bordello where Hemingway refereed boxing matches.
314 Simonton St.
When the car Papa planned to pick up in Key West was delayed, he stayed six weeks above this former Ford dealership revising A Farewell to Arms.
Captain Tony's Saloon
At the original location of Hemingway's main bar, Sloppy Joe's, check out decades of dollar bills (and stuff) tacked to the ceiling.
90 Miles to Cuba
Artist Linda Reike curates vintage finds including rare books, nautical antiques, jewelry, and 1930s postcards from Key West and Cuba.
Books & Books
This lovely indie bookstore was founded by Judy Blume and is ground zero for Key West's literary scene.