It’s nearly three-quarters of a mile from Sloppy Joe’s bar to the house behind the wall at 907 Whitehead Street. Ernest Hemingway made the walk countless times, drunk, sometimes angry, maybe lost in thought, happy from a good day fishing or not thinking about anything at all. He used to joke that living near the town’s lighthouse ensured he could always find his way home from the bar, and so it likely did.

The lighthouse would have been one of the first buildings to come into view as Hemingway and his wife Pauline first sailed into Key West in 1928, and one of the last things the writer saw as he left, alone, in 1939. During those years he produced some of his most endearing literary works, drank, fought, wrecked a marriage, named a bar, discovered saltwater sport fishing and gave the city at the end of the road a legacy of sorts. In return, Key West expected nothing of him, took nothing and posed only one real constant challenge: To spend the day drinking, fishing, or both?

Home

It was a walking town, with most everything you’d want to get to shoved in a few square miles at the west end of the island. Key West, not technically tropical (above the Tropic of Cancer) but it may as well be with its warm breezes, palm gardens and cool mornings. It was mornings that found Hemingway writing, going through a handful of No.2 pencils—seven pencils was a good day’s work—or punching out a couple hundred words on his Royal typewriter before heading into town. The studio in which he finished A Farewell to Arms and created such works as For Whom the Bell Tolls, Death in the Afternoon and Green Hills of Africa, is on the top floor of an old carriage house behind the main house on Whitehead Street, connected to the master bedroom by a catwalk. Sitting among various hunting trophies and reminders of his travels, he would have enjoyed the calm about the place, which remains even today.

The house is a grand piece of work, built in 1851 on the second-highest piece of ground in Key West (the highest holds the cemetery) by a marine architect and salvage wrecker named Asa Tift. Remarkably for Florida it has a basement, which Hemingway used as a wine cellar. He and his wife filled the house with furniture from around the world—Venetian glass chandeliers, woodwork from Spain, a cigar-maker’s chair from Cuba—and added a brick wall for privacy in 1935 after the residence appeared on a tourist map. For a time, 907 Whitehead St. was a happy home for the couple and the numerous six-toed cats Hemingway kept on the property.

It saw the birth of their two sons, Patrick and Gregory, and hosted frequent parties and visits from friends, but the house was also the setting for numerous dramas and, ultimately, the family’s dissolution. Of course that came after the writing, after the fishing, and long after the bar. The bar, in fact, is where you might say it all started. Started and ended.

Sloppy Joe’s

The floor at Jose Garcia’s Rio Havana club was a mess: wooden planks soaked from large chunks of melting ice that were cooling down the fresh seafood for sale. “Sloppy Joe’s,” patrons jokingly called it. Along with fish the place sold booze, which is why Hemingway and his friend Joe Russell stopped by on their frequent angling trips to Cuba. Back in Key West, Russell (also called “Josie”) chartered fishing boats and operated a speakeasy, making him an immediate friend to Hemingway.

When Prohibition ended, Josie went legit and opened a bar called the Blind Pig (proxy term for an illegal drinking joint) but Hemingway preferred the humorous moniker from their Cuban haunt. So Sloppy Joe’s for Jose Garcia became Sloppy Joe’s for Joe Russell, and a legendary watering hole was born. It’s said the place didn’t have a door—and didn’t need one because it never closed. Rowdy, basic and pouring a constant stream of drinks, the bar was moved one night—literally—after a $1/week rent increase encouraged Russell to buy a building down the street and change addresses. In exchange for free drinks, patrons were invited to grab their seats, the tables, their half-finished beers and anything else they could carry and take it half a block to the new spot at 201 Duval Street, where Sloppy Joe’s still operates today. As Dave Gonzales, a Key West native and guide at the Hemingway house tells it, the crowd even ripped out the bathroom fixtures, which Russell owned, and moved them as well. Josie didn’t need the toilets and sinks—the bathroom at the new location was already installed—and so the whole mess was dropped on the sidewalk out front. When Hemingway saw one of the urinals lying there, he decided it would make a great watering trough for the numerous cats he kept at his house. And so, after a few drinks, Gonzales says Hemingway and Russell dragged the large porcelain urinal the three-quarters of a mile down Duval St. to Hemingway’s home and dumped it in the backyard, where it sits today. Pauline, not pleased, covered the urinal with Spanish tiles in hopes of disguising its true form.

The bar was Hemingway’s home away from home. It hosted “The Mob,” Key West’s version of the Rat Pack. Hemingway, his friend Charlie Thompson, Russell, a local boat captain named Eddie “Bra” Saunders and a handful of others would meet there and solve the world’s problems over drinks. The bar was where Hemingway threw more than a few punches, though most of his proper fights happened elsewhere, and it’s where he launched—and finished—most of his fishing trips. It’s also where he met Martha Gelhorn, but we’ll get to her later.

The Mob

The day after he moved to Key West (first visiting on the advice of writer John Dos Passos), Hemingway met Charles Thompson. Thompson’s family was one of the best off in town, but Charlie was a down-to-earth guy, an avid fisherman and hunter who ran the local hardware store. In addition to introducing Hemingway to saltwater sport fishing, an activity the writer pursued for the rest of his life, Thompson and his wife Lorine became close friends of the Hemingways. Thompson even accompanied the couple on their epic nine-month African safari in 1933, with a stopover in Paris during which he managed to get drunk with James Joyce, who’d just finished Ulysses and who Thompson later referred to as “a grand little man.” Thompson was a charter member of Hemingway’s Mob, as was Russell. More joined in when Hemingway sent letters to his Paris friends asking them to come down to “St. Tropez for the poor,” as he called Key West, and of course there were the locals.

All together, the Mob would drink, gamble, fish, go swimming and spend their days doing not much of anything and their nights carousing. Perfect Key West living.

Living and The End There was Pilar, a 38-foot fishing yacht named for a bullfighting shrine in Spain (Pauline thought it was named for her as “Pilar” was one of her nicknames). It was Hemingway’s dream boat and a lifelong companion, ferrying him and his friends on numerous multi-day fishing adventures and ultimately to Cuba, where it sits in dry-dock today. There was the night he punched a drunk Wallace Stephens into a puddle after the poet upset Hemingway’s sister Ursula at a cocktail party. Backyard sparring in his private boxing ring, hundreds of marlin and tuna pulled from the sea, madness in Cuba including the Havana dalliance with Jane Mason, wife of a major Pan Am investor and friend of Hemingway’s, the book To Have and Have Not, the only novel he set in the United States and a book he reportedly didn’t like… Hemingway’s Key West adventures held a pile of good times and a few messes as well, but none of it mattered as much as a meeting he had in 1936 at his beloved Sloppy Joe’s. That encounter, with Martha Gelhorn, really was the beginning of the end.

Hemingway’s wife, Pauline Pfeiffer, was a graduate of the Missouri School of Journalism. She’d been in Paris on assignment for Vogue when she met the writer and his first wife, Hadley. Despite being a devout Roman Catholic and a friend of Hadley’s, Pauline began an affair with Hemingway, and eventually married him in 1927. Pauline’s family was wealthy and it was her uncle Gus who purchased the Key West home for the couple, for $8,000 in 1931. He’d also purchased a new car for them upon their arrival. But just five years later, the marriage came full circle and the happy days were over. One night at Sloppy Joe’s, Hemingway met Gelhorn, a stunning blonde. As the story has it, she was looking great in a black sundress, he was looking like hell in a dirty shirt, frayed sandals and a pair of Bermuda shorts held up by a piece of rope. However it happened, the two began carrying on an affair—and not discretely. One year later, both were in Spain covering the civil war for various publications while Pauline was home in Key West trying to salvage her marriage. Knowing Hemingway enjoyed swimming, she had a private pool installed next to his writing studio. But her attempt to please him backfired. When he returned he grew furious at the pool’s price—$20,000—and reportedly took a penny from his pocket and threw it at his wife, declaring, “You might as well have my last cent!” The money for the pool, the house, the 1933 African safari and a few other adventures wasn’t Hemingway’s, of course, which may have been part of the problem for the macho writer. In any case, Hemingway began spending more and more time in Spain and in Cuba, where he had a house with Martha. His Key West friends cooled to him, mostly siding with Pauline over the affair, and his marriage effectively ended. In late 1939, after some time in Sun Valley, Idaho, a new favorite haunt, he returned to Key West in hopes of spending the holidays with Pauline and his sons, but they’d left for New York in advance of his visit. He spent Christmas alone in the house, and on December 26 packed his things and boarded the ferry for Cuba, ending his Key West days. For her part, Pauline had the penny pressed into cement under glass next to the pool, where it remains today.

Now Today, Sloppy Joe’s is a madhouse, as known for its Hemingway T-shirts as it is for being a bar. Those hoping to stop by on a weekend for a quiet drink in remembrance of “Papa,” as the locals called Hemingway, will be sorely disappointed to learn they’ve little hope of seeing the bar, much less sitting at it quietly.

Standing-room-only crowds and live music are common in the high season, making it near impossible to study the various bits and pieces of Hemingway memorabilia on the walls, much less order a “Papa Dobles”—a mix of rum, grapefruit, grenadine, sweet and sour, club soda and lime, advertised as “Papa’s favorite!” The original site of the Blind Pig is still a bar as well, “Captain Tony’s,” and Hemingway’s house is a tourist attraction. The studio is still there, much as he would have left it. So are the urinal/water trough and the six-toed cats. But the small-town intimacy of the island has, to some degree, given way to a kind of “bikers on spring break” atmosphere, which is neither bad nor good exactly. It’s tough to say how Hemingway would find Key West today, but decades ago, a world away from the lights of 1920s Paris and the cocktail company of Gertrude Stein, Picasso and the rest, the writer found a place that takes all comers as they are and allows them to be themselves. For better or worse, that hasn’t changed.

For more on Hemingway’s Key West, read Stuart B. McIver’s useful book of the same title, a valuable resource for this article. And be sure to visit Dave Gonzales and the team at the Hemingway home in person or online at hemingwayhome.com