Last updated on January 6th, 2026 at 09:32 am
Ernest Hemingway ended up in Key West like many others — by accident.
He came for a day and ended up staying for a decade. That was close to a century ago, and the town has yet to recover from his presence.
Papa’s spirit permeates the island. His former home, complete with a gaggle of six-toed cats, remains one of the most popular tourist attractions. Each July more than 100 white-bearded men wearing sweaters and safari khaki shorts storm the streets for the largest look-alike contest in the world.
Thanks to Hemingway, Key West endures as a haven for writers and other artists.
It is easy to simultaneously admire and curse the man. He was an imposing character, a larger-than-life egoist heavy of drink and quick of wit. He slayed hundreds of animals, hunted Nazi U-boats with hand grenades, survived two plane crashes, gunned down sharks with a Thompson submachine gun to save his tuna catch (it didn’t work), won Pulitzer and Nobel prizes, inspired generations of creative talent, and once reassured F. Scott Fitzgerald that his penis was of a standard size.
To this end, a truly honest Hemingway-style experience in Key West could entail instigating a number of bar brawls, stealing the urinal from your favorite drinking establishment, getting a divorce or two and spending your last penny.
Ideally, however, it will not need to include any of those because there are more imaginative ways to revel in Hemingway’s Key West, most of which do not involve jail time and liver damage.
Experience Key West like Hemingway
Fish the Northwest Passage
Locals call the remains of the Northwest Passage lighthouse off Key West the “Hemingway Stilts” after the avid angler who cherished this fishing hole. It might be a stretch to break his world record of landing seven marlin in a day, but you’re bound to at least get some yellowtail and grouper for dinner.
TripAdvisor: Key West fishing charters
Indulge in Life’s Pleasures
Hemingway savored food, drink and friends, and often during his travels sought out the finest meals and drinking establishments. Grab some companions for a delectable breakfast at Blue Heaven, the former home of his boxing ring, then mosey over to Sloppy Joe’s or Capt. Tony’s Saloon, both buildings in which he downed many a libation. For extra authenticity and hangover eschew, avoid his nemesis, blended and sweetened concoctions.
Related story: Most Beloved ‘Locals’ Bars in Key West
Get marooned in the Dry Tortugas
It was 1930 when a storm blew in, stranding Papa and his fishing crew for two weeks on Garden Key, 70 miles west of Key West. They hid in a shed at abandoned Fort Jefferson, braved the wind to catch what fish they could, and mostly survived off of the 24 cans of spaghetti and 12 cans of beans they happened to bring along. It’s not recommended to brave the Tortugas in a storm, but it is a healthy adventure to camp there for a few nights. Plus, SpaghettiOs do taste a lot better when eaten on a beach under starlight.
Related story: Camping at the Dry Tortugas National Park
Be inspired at the Hemingway Home and Museum
A National Historic Landmark, the Hemingway Home in Key West was his residence for more than a decade, where he wrote some of his most famous works including “To Have and Have Not.”
Cat-lovers put this on their list of things to see because it is home to a colony of cats, many of whom are descendants of Hemingway’s original six-toed cat, Snow White.
The Spanish Colonial Home was built in 1851 and Hemingway added Key West’s first in-ground pool in 1938. It’s extraordinary — huge (24 feet wide and 60 feet long), dug out of coral rock, and unusually deep. (The shallow end is 5 feet deep and the deep end is 10 feet deep.) Water has never been plentiful in Key West and this pool was built with a pump to fill it with salt water. It was also extraordinarily expensive — $20,000, and that was during the Great Depression.
Here’s a link to the Hemingway Home and Museum.
Try On Your Own Legendary Style
“Whatever your style, find it and flaunt it,” is not a quote by Hemingway, but it could be about him. Key West is known for its come-as-you-are acceptance of all people. So what better place to find your defining style and the confidence that comes with it? Just as Hemingway is forever known for his sweaters and Jimmy Buffett for his lack of shoes, there’s a new set of duds waiting for you somewhere in town, poised to create the next legendary look.
Discover your style at these Key West specialty shops on Tripadvisor
Experience one good, true adventure
Hemingway traveled widely, experienced much, learned courage and lived life for each savory moment. There’s no better way to exploit Key West Hemingway style than adventuring outside of your comfort zone. Learn to scuba, ride a parasail or finally get up the nerve to ask out that lovely gal or handsome guy you’ve been eyeing. It might be intimidating, but ultimately no one regrets a grand adventure.
Here’s a link to Key West adventures on Tripadvisor
we were there in Feb. We will go back. Loved it
Thanks for this great article!! I’ve always been one of those people who “simultaneously admire and curse the man.” In someways I want to be like him in the sense of living life to the fullest and having adventures, and in others ways I want to be nothing like him–such as my relationship with my family. Also, thanks for the pic of the look-alike contest. I’ve always heard about it, but never actually seen what it looks like!