Hemingway in Key West

By: Claire Bullen

February 3, 2015

Ernest Hemingway may have been one of the 20th century’s leading literary luminaries, but Hemingway in Key West? Here, they just call him Papa.

Throughout his life, Hemingway came to be strongly tied to the places he lived and worked. Those who’ve read A Moveable Feast (or who have seen “Midnight in Paris”) associate him with the City of Lights, while, particularly in his later years, his name became synonymous with Havana (and the Floridita bar). And Florida? Hemingway and his second wife Pauline moved down to Key West in 1928 and lived here, on and off, for the next 10 years. While they only came down to buy a car, Hemingway was soon swayed by the tropical breezes, the relaxed pace”¦and the never-ending supply of daiquiris.

Hemingway in Key West | Hemingway House And Museum
A trip to the Hemingway Home and Museum is a must © Rob O’Neal Photography

Those looking to follow in Papa’s irascible footprints have plenty of stops to make on their literary tour of Key West, where he’s still regarded as something of a patron saint. From landmarks and museums to a gloriously kitschy festival held in his name, there’s plenty to see and do – just make sure you brush up on A Farewell to Arms first.

Hemingway in Key West | Hemingway Cat
You won’t have to look far to find the six-toed ‘Hemingway cats’ © Rob O’Neal Photography

The first stop on any Hemingway in Key West tour should begin at the Hemingway Home and Museum. Located at 907 Whitehead Street, the two-storey house was originally built in 1851, and today looks much the same as it did when Hemingway lived and worked within its walls. One especially noteworthy feature? The fact that the property is home to a huge colony of cats – many of them six-toed, these so-called “Hemingway cats” are descendants from the dozens that Hemingway owned in his lifetime. Tour guides lead visitors on a timeline of Hemingway’s time in Key West, all while ensuring the feline residents are comfortable and well cared for.

Hemingway in Key West | Sloppy Joes Bar
Hemingway’s favourite bar, Sloppy Joe’s is still a popular landmark © Rauluminate/iStock Editorial/Thinkstock

Hemingway was such an avid tippler that his favourite cocktail soon came to be appended with his name; to sample one of those infamous Hemingway daiquiris, head over to Sloppy Joe’s Bar, which was the author’s preferred Key West watering hole. After opening in 1933 (on the very day that Prohibition was repealed), Sloppy Joe’s quickly became local legend, thanks in part to Hemingway and his literary mob who regularly descended on the place. Today, the bar still serves up the delicious cocktails (here called “˜Papa Dobles’) that he liked so much.

Hemingway in Key West | Hemingway Days Festival
The Running of the Bulls is a quirky part of the annual Hemingway Days Festival © Andy Newman/Florida Keys News Bureau/HO

For those truly devoted to celebrating the author’s legacy, the best time of year to visit Key West is when the city holds its annual Hemingway Days Festival. Returning this year in late July for its 35th anniversary, the festival is equal parts reverence and kitsch, and comprises readings, talks, a marlin fishing tournament, a cheeky “˜Running of the Bulls’ and especially the infamous Papa Look-Alike Contest, which sees dozens of white bearded, sweater-wearing men sweat under the Florida sun for the chance to take home top honours (the competition is held at Sloppy Joe’s, naturally).

Hemingway in Key West | Hemingway Lookalikes Contest
The Papa Look-Alike Contest sees dozens of Hemingways compete for top honours © Andy Newman/Florida Keys News Bureau/HO

And for the curious, there are still more traces of Hemingway around town – Casa Antigua, for instance, once the Trev-Mor Hotel, which he stayed in upon first moving down to the Keys. Just be cautious of hanging around too long: you may just decide to stay put for the next decade, like Papa himself.


Virgin Atlantic operates direct flights to Miami from London Heathrow, making it easy to discover the legacy of Hemingway in Key West.


Have you gone on a Hemingway in Key West tour? Share your favourite sights in the comments below.

Written by Claire Bullen

Claire Bullen

Claire Bullen

Claire is a born globetrotter: before relocating to London, she spent time in New York, Paris, Philadelphia, Chicago, and San Francisco. When she's not in pursuit of the next exciting meal, she can be found haunting indie bookstores and sketching outdoors. Follow Claire @ClaireMBullen

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