He was broke when he first stepped off the ferry in 1928. Well, not quite broke, but definitely not the titan of American letters we picture today. Ernest Hemingway arrived in the Florida Keys by accident, really. A delayed car delivery forced him and his second wife, Pauline, to wait around.
They stayed. They stayed for over a decade.
Key West wasn't a luxury resort back then. It was a gritty, salt-stained wrecking and fishing village that had seen better days. The Great Depression was about to kick the door in, and the island was basically bankrupt. But for Hemingway, this isolated limestone rock was exactly what he needed to turn into "Papa."
The House That Changed Everything
You can't talk about Ernest Hemingway Key West without talking about 907 Whitehead Street. It’s a massive Spanish Colonial house made of native limestone. Honestly, it was a bit of a dump when Pauline’s Uncle Gus bought it for them for $8,000 in 1931.
The place had no running water. It was boarded up. But it sat on the highest point of the island—a whole 16 feet above sea level.
Hemingway loved it. He built a brick wall around the property to keep the tourists out. He hated the "lookie-loos." He eventually added the first in-ground pool in Key West. It cost $20,000, which was an insane amount of money in the 1930s. Legend says he got so mad at the price that he took a penny from his pocket and pressed it into the wet cement.
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"You might as well take my last cent," he told Pauline.
If you go there today, you can still see that penny. It’s a 1934-D copper cent, still stuck in the concrete near the pool.
Those Famous Six-Toed Cats
Then there are the cats. You’ve probably heard of them. Polydactyl cats.
It started with a kitten named Snow White. A sea captain gave her to Hemingway because sailors thought extra toes were lucky for catching mice on rocking ships. Today, about 50 or 60 descendants of Snow White still run the grounds.
They have the run of the place. They sleep on the furniture. They have their own cemetery. About half of them have the physical six-toe trait, but they all carry the gene. If you visit, don't try to pick them up—they're local celebrities and they know it.
The Writing Studio: Where the Magic Happened
Hemingway was a creature of habit. He’d wake up at sunrise, even if he’d been closing down the bars the night before. He’d walk across a second-story catwalk from his bedroom to a private studio above the carriage house.
He wrote standing up.
He claimed it kept him focused. In that small, humid room, he hammered out some of the most important books in American history. We’re talking:
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- A Farewell to Arms (he finished it here)
- To Have and Have Not (his only novel actually set in Key West)
- The Snows of Kilimanjaro
- Green Hills of Africa
Basically, the 1930s were his prime. The island provided the "clean, well-lighted place" he needed to work before the heat of the afternoon made thinking impossible.
Drinking with the "Mob" at Sloppy Joe's
Once the writing was done, usually by noon, Hemingway headed for the water or the bar. Mostly both.
His best friend was Joe Russell. Joe ran a speakeasy during Prohibition and then opened the legendary Sloppy Joe’s Bar. Hemingway didn't just drink there; he was a fixture. He called his group of friends "The Mob." They were a mix of local characters, charter boat captains, and famous writers like John Dos Passos.
The Urinal Incident
There’s a weird story about a urinal that sounds fake, but it's 100% real. When Sloppy Joe’s moved locations in 1937 to its current spot on Duval Street, Hemingway decided he wanted a souvenir.
He claimed he’d "pissed away" enough money in that urinal to own it.
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He and Joe Russell literally carried the heavy porcelain fixture down the street and plopped it in Hemingway's yard. Pauline was horrified. She tried to hide it by turning it into a tiled water fountain for the cats. It’s still there today, right next to the pool, serving as a very historical cat bowl.
Why He Finally Left for Cuba
By 1939, the vibe had changed. Key West was becoming a "tourist trap" in Hemingway's eyes. The government was trying to revitalize the island's economy by promoting it as a vacation destination.
He hated it. People were knocking on his door.
Plus, his marriage to Pauline was falling apart. He’d met a young, ambitious war correspondent named Martha Gellhorn at Sloppy Joe’s. She was the opposite of Pauline—she wanted to be in the middle of the action, not living a domestic life in the Keys.
Hemingway eventually followed Martha to Cuba, settling at Finca Vigía. He kept the Key West house until his death in 1961, but he never really lived there again.
What You Should Actually Do in Key West
If you're heading down there to find the ghost of "Papa," don't just do the standard tour and leave. The Ernest Hemingway Key West experience is about the atmosphere.
- Visit the Museum Early: It opens at 9:00 AM. Go then before the cruise ship crowds turn the garden into a parking lot. It’s cash only, so don't show up with just a credit card.
- Grab a Drink at Capt. Tony’s: This was the original location of Sloppy Joe’s. This is where Hemingway actually sat and drank while he was living on Whitehead Street.
- Check out the Seaport: Walk the docks where the Pilar (his 38-foot fishing boat) used to be moored. You can still feel the "Conch Republic" grit if you look past the souvenir shops.
- Look for the "Hemingway Days" in July: If you want total chaos, go during his birthday week. They have a massive look-alike contest where hundreds of bearded men in white safari shirts take over the island.
Key West isn't the quiet escape it was in 1931. It’s loud, it’s expensive, and it’s crowded. But if you stand on the balcony of that house and look toward the lighthouse across the street, you can still see why a restless writer from Chicago decided this was the center of the world for a while.
Your next move for the trip: Check the local weather patterns for your visit. Key West is beautiful in the winter, but if you're going for the "Hemingway Days" festival in July, be prepared for 90-degree humidity that feels like a wet blanket. Also, remember that the Hemingway Home still only accepts cash for admission, so hit the ATM before you get in line.