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Ernest and Pauline Hemingway in Paris, 1927
Ernest and Pauline Hemingway in Paris, 1927

Hemingway's Floridays in Key West

Writers have always loved the Florida Keys, whether it was Tennessee Williams, F. Scott Fitzgerald, Hunter Thompson, Zane Grey, Robert Frost, Truman Capote or Jimmy Buffett.

They all came for a touch of the tropics, the beautiful blue waters, incredible fishing, the white sandy beaches, plus it almost feels like you’re in another country.

You could toss your watch and shoes, because things just move slower down there,  like Island time,  where people are more laid back.

It’s most famous resident from the literary world was American novelist and journalist Ernest Hemingway.

People come down to Key West today to drink in the same watering holes the hard drinking writer frequented,  tour his house and pet the descendants of the six-toed cats that roam the property.

Hemingway was a fellow member of the cafe society “Lost Generation” of expatriate artists and writers populating Paris during the 1920s.

He was finally making money from his novel “The Sun Also Rises”, when he moved to Key West with his new wife Pauline Pfeiffer in 1928.

They lived in an apartment for 3 years until Pauline’s wealthy Uncle Gus bought them the two-story Spanish Colonial house at 907 Whitehead Street for $8,000.

The Hemingway’s spared no expense on their new home as it became the town’s showpiece and still is

Hemingway’s Key West was a town  unlike any place he ever experienced.

It was filled with interesting people ranging from well-to-do businessmen, lawyers, down on their luck fishermen, shipwreck salvagers, smugglers, and scallywags (a person who behaves badly but in an amusingly mischievous rather than harmful way).

Ernest’s friends Charles Thompson,  Joe Russell (Sloppy Joe) and Captain Eddie “Bra” Saunders, together with his old Paris friends,  became known in Key West as “the Mob”.   They would go fishing in the Dry Tortugas, Bimini and Cuba for days and weeks at a time in pursuit of giant tuna and marlin.

Everyone in “the Mob”  had a nickname, and his was “Papa”.

Papa would referee local amateur fights in Bahama village, where the Blue Heaven restaurant is today.

Throughout his career he freely used the people and places he encountered in his literary works and many appeared as characters in his novels.

His feuds with other writers, his fist fights with other drunken stumblebums in town, and the alcohol they consumed at Sloppy Joes was a way of life.

He rose an hour before daybreak to begin writing (hangover or not) and usually finish by late morning.

Rarely using a typewriter except for writing dialogue, he preferred blue backed notebooks, two pencils and a pencil sharpener.

He had an average output of 400 to 700 words a day.

His declarative sentences that packed an emotional wallop and his over the top macho from his experiences permeated his work.

In 1934 Hemingway bought a 38 ft boat from Wheeler Shipbuilding in Brooklyn for $7,495.   He named it Pilar which was his nickname for his second wife Pauline.

Pilar was a sassy fishing boat with a shiny black hull,  she carried a phonograph,  slept six and had two engines,  one for trolling the other for cruising at a top speed of 16 knots.

During World War II Hemingway used the boat to search for German U-boats in the Caribbean waters.  His armament included a Thompson submachine gun and grenades.

He mostly used the machine gun to shoot at sharks to ward them off while hauling in large marlin.

More of a farce to get them extra gas rations and immunity from Cuban police for driving drunk, these adventures inspired him to write his novel “Islands in the Stream”.

When he wasn’t writing, he was boxing friends and enemies in the ring he set up in his garden, drinking with friends,  arguing with friends,  because that’s what men did.

Hemingway loved to write while relaxing out on his boat or his home.

He finished his semi-autographical World War I novel “Farewell to Arms” and his bullfighting book “Death in the Afternoon”.

He next wrote the novel “To Have and to Have Not” about smuggling during the Depression and perhaps his greatest short story,  “the Snows of Kilimanjaro”.

Ernest’s lifestyle in Key West is legendary,  he wrote well, drank hard, was a game fishing enthusiast and spent a lot of time in Sloppy Joes Bar, located at the current site of Captain Tony’s on Greene Street.

Sloppy Joes was a rough place, where drinks were cheap and fights were common.

Originally built an 1851 as an ice house, in the center of the bar is an old tree that was used to hang 17 people.

During one particularly heavy night of drinking Hemingway informed Sloppy Joe Russell that he would be taking his favorite urinal home with him, since Russell was moving locations.

He felt he deserved to salvage at least the urinal since he had pissed away enough money in it.

Pauline converted the urinal into a fountain outside the home where it’s still stands.

In 1935 a tourist guidebook published a map of Key West attractions and Hemingway’s was listed.

At home gawkers were trying to glimpse the famed author at work so he hired a local bricklayer to erect a 6-foot  wall that remains to this day.

In 1939 Key West became too touristy for Hemingway, but truth was he had a new girlfriend,  his wife found out,  and another marriage was done.

After living in Key West for nearly a decade, he moved to Cuba.   He got a large check for the movie rights to “For Whom the Bell Tolls” in 1940, so he ran off and married wife number three Martha Gellhorn.

She was a war correspondent and he traveled the world with her until they got sick of each other.

He married again to a real outdoors woman,  Mary Welsh who could fish, shoot, swear and put up with his moods.

He continued to visit Key West during the 40s and 50s and in 1954 he published “The Old Man and the Sea’ and it captured the Pulitzer and Nobel Prize.

On July 2nd 1961 at his home in Ketchum, Idaho,  he was found dead with a shotgun wound to the head.

His house is a National Historic Landmark and it’s open daily from 9:00 to 5:00.

All of the house’s rooms are open to visitors except for Hemingway’s writing room which can only be seen through a screen.

Go upstairs to his bedroom and gaze down at the town’s first swimming pool. Beyond that a bungalow with its walls surrounded with animal heads, skins and stuffed fish.

The tour takes 30 to 45 minutes and admission is only $19.00.

His home and hangouts are all down there waiting for you right off Route 1.

David Garland FL Key West Apr 24, 2025 History Museums Places to Visit

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Location: Key West, FL

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David Garland
Apr 24, 2025
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I saw the Pilar when I visited Cuba.  She was "yar"!
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Peter commented: "I saw the Pilar when I visited Cuba. …" 2 weeks ago
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