Key West, the bottommost tip of the Florida Keys, is one of my favorite places in the world.
Ever since I first visited on a two-week long road trip through Florida with my now in-laws while I was in college, I’ve been hooked.
Crystal clear, turquoise waters filled to the brim with tropical fish that you can snorkel out to see right from the beach. Historic buildings lining palm tree-fringed streets. Quirky locals hawking drinks sold in hollowed out pineapples and coconuts chopped open fresh when you order them. A nightly celebration where the whole city gathers to watch the most beautiful sunsets you’ve ever seen.
It’s a nearly 3-hour drive to get there from the mainland of Florida on the famous Overseas Highway that stretches 113 miles through the Florida Keys before ending in Key West.
The city feels a bit like its own country, as separated as it is from the rest of the state and with its own customs and lifestyle. The locals agree, and fondly refer to it as the ‘Conch Republic.’
Since my first visit almost six years ago, I’ve been back five times. And every time I visit, I see something new or learn something I didn’t know about the history of this fascinating place.
One thing I continue to learn about with each visit is the connection that one of my favorite authors, Ernest Hemingway, had to Key West.
Who is Ernest Hemingway
If you don’t already know, Ernest Hemingway was an American best known for his fiction writing. He penned a number of now-classic titles, including “The Sun Also Rises,” “For Whom the Bell Tolls,” and “The Old Man and the Sea.”
Hemingway led a famously colorful life. When he was just 18, he worked as an ambulance driver for the Red Cross, serving in Europe during World War I where he was seriously injured. Before returning home, he met and fell in love with an older woman who he would later propose to, only to be later rejected when she fell for another man.
He became a journalist and war correspondent who traveled the world and spent a lot of time living abroad and in Cuba. He was a passionate outdoorsman who enjoyed deep sea fishing and big game hunting. He married four times, often cheating on his current wife with his future one, or leading other extra-marital affairs, perhaps as a result of the rejection from his first love. He smoked and drank to excess, which likely contributed to his suicide in 1961.
Somewhere in the middle of all that, he landed in Key West.
Ernest Hemingway in Key West
Ernest Hemingway discovered Key West almost by accident. He and his then-wife, Pauline, had traveled from Paris where they had been living to Havana, Cuba in April of 1928. They were on their way to Pauline’s family estate in Arkansas, and then on to Kansas City where they planned to live while Pauline gave birth to their son.
Pauline’s wealthy uncle had ordered the couple a motorcar from Ford. They crossed the 90 miles of ocean from Havana and arrived in Key West expecting to stay just two days. But when their car wasn’t ready upon their arrival, the Ford dealership insisted on putting the couple up in an apartment above their shop.
They would end up staying for several weeks, during which Hemingway fell in love with Key West.
The pair would return and rent houses each winter from 1928 to 1931. In April of 1931, the Hemingway’s, again with a lot of help from Pauline’s uncle, purchased a home. It would remain their primary residence until 1939, though Hemingway traveled to Spain at length to work as a war correspondent, where he fell in love with his next wife. He left Key West in 1939 and moved to Cuba with his new wife, leaving Pauline and her sons to continue living there until her death in 1951.
Hemingway House
Whether you like the famous author or not, the Hemingway House is a must-see. I am not someone who likes to revisit museums that have an entrance fee, but this is one that I happily pay for on every trip to the islands.
The home is embodies everything that is Key West. A sweeping patio, large windows, shading palm trees, a sparkling blue pool out back. And it’s filled to the brim with six-toed cats. Nope, not a typo.
Hemingway was gifted the first polydactyl cat to live on the property, and he has since reproduced. There are dozens of cats on the property, though many sport just 5 toes. Before you think I’m sending you to a feral-cat-sanctuary, know that these cats have it better than your average housecat, with air-conditioned homes, food bowls, and more scattered in all around the garden out back.
If it’s your first visit, I recommend joining one of the tours included in your gate fee. Now when I go back, I prefer wandering sans-crowds of other tourists. The writer in me loves imagining such a famous author spending his days in his office above the garage out back, gazing out the window and drawing inspiration from the beautiful island surrounding him.
Other Hemingway Hide-Outs
Hemingway rose to fame while living in Key West, so the places he frequented were well-documented. You can still visit his favorite bar, Sloppy Joe’s, although it has moved locations since his time. The actual bar he visited is now called Captain Tony’s.
You can wander the garden at the home that was once the Ford dealership that housed the Hemingway’s in the upstairs apartment. You can eat at the restaurant, Blue Heaven, that now occupies the building that was once a saloon where Hemingway would eat breakfast and referee boxing matches in the courtyard. You can order the Cuban coffee that Hemingway likely enjoyed from stands and restaurants throughout the city.
And of course, you can cast your line and try to reel in your own fish legend just as he spent many a morning and afternoon trying to do.
I’ve not made it to the Keys yet this year, but this post has me thinking that a trip might be in order sooner rather than later! One of the reasons I go the Keys, and Florida in general, so often is that cities like Orlando and Ft. Lauderdale are hot spots for budget airlines! Check out this guide to learn more about booking a flight on a budget airline.
Cate Goes 