Exploring Ernest Hemingway’s Key West While Visiting Florida  

Key West has seen its fair share of famed literary figures pass through, but if there’s one person who really left a mark on this place it’s Ernest Hemingway.

I only had a couple of days in town on my recent trip across the Florida Keys, but I wanted to discover Hemingway’s Key West, so even with limited time, I made it my mission to hit up as many spots as I could connected with this famed writer.

For any other Hemingway fans out there, here’s a look at some places you’ll want to track down on your next visit:

Blue Heaven

Blue Heaven is an establishment steeped in history. Over the course of its existence it has been a dance hall, a bordello, and it also hosted cock fights, gambling and Friday night boxing matches refereed by the one and only Ernest Hemingway. I couldn’t explore Hemingway’s Key West without dropping by this iconic venue, so on my first morning there I ventured for brunch.

Blue Heaven is a really cool spot with a super laid-back feel. They have blue-shuttered windows, a shaded courtyard surrounded by lush palms, oh, and the food is amazing! They know how to do brunch galore, so you’ll want to bring your appetite. If there’s one item that you absolutely need to order off the menu it’s the Lobster Eggs Benedict.

Picture toasted English Muffins with avocado, lobster, bacon strips, tomatoes, and poached eggs covered in a hollandaise sauce, with a side of tropical fruits that include honeydew melon, pineapple, and cantaloupe. And if that wasn’t a big enough brunch, I also ordered a slice of Key Lime Pie, a fruit smoothie, and I may have sneaked a bite from someone else’s Banana Bread.

Suffice it say, the food at Blue Heaven is incredible!

Address: 729 Thomas Street

Hemingway House

After brunch at Blue Heaven, I walked over to Hemingway’s House. My favourite part about this visit was hearing the stories behind Hemingway’s home. I decided to take the guided tour and I ended up with the most passionate guide who was basically a walking encyclopaedia on anything related to Hemingway.

The best story of the day was learning how the house got its swimming pool. It turns out that while Hemingway went off to cover the Spanish Civil War (in the company of another woman!), his second wife Pauline decided she would build a massive swimming pool over his beloved boxing ring.

When Hemingway returned and learned that the pool had cost a whopping $20,000, he was furious. So he took a penny out of his pocket and angrily tossed it on the ground telling her, “You’ve spent all but my last penny, so you might as well have that!” Seeing as the concrete was still fresh, Pauline took the penny and imbedded it into the cement where you can still see it today.

Of course we can’t speak of Hemingway’s home without mentioning the 50+ polydactyl cats that call this place home. The six-toed cats are the descendants of Hemingway’s pet cat Snow White. Most of them are a friendly bunch used to visitors streaming through, so they’ll give you a pose or two and allow a bit of a scratch.

Address: 907 Whitehead Street

Key West Lighthouse

From Hemingway’s Home I walked across the street to the Key West Lighthouse. It is said that after a late night at the bar, Hemingway would stumble out onto the street and use the lighthouse as a marker to find his way home. The lighthouse may not be as easy to spot from across town nowadays, but you have to think that when Hemingway lived here the palm trees would have been quite a bit shorter.

It’s 88 steps to the top and you get some pretty cool panoramic views of Key West. We could even see a cruise ship off in the distance on the day I visited. When you visit the lighthouse, you also get access to the Keeper’s Quarters Museums where they have regular exhibitions.

Address: 938 Whitehead Street 

Sloppy Joe’s Bar

“Always do sober what you said you’d do drunk. That will teach you to keep your mouth shut.”

Hemingway loved his mojitos, so my next logical stop was his local watering hole, Sloppy Joe’s Bar, which was owned by his good friend and fishing companion Joe Russell. It is said that Hemingway had a bit of influence when it came to naming this place. Apparently Sloppy Joe’s got its name from the original Sloppy Joe’s bar in Old Havana that sold liquor and iced seafood. Because the ice would melt quickly in the Cuban heat, patrons taunted the owner José García Río (or just Joe in English) that he ran a “sloppy” place.

Now before you track this place down, I should mention that the original location of Sloppy Joe’s at the time Hemingway frequented was a few doors down on 428 Greene Street and is now called Captain Tony’s Saloon. Sloppy Joe’s changed location after Russell refused to pay the rent increase from $3 per week to $4. It is said that since a nearby spot was vacant, customers simply picked up their drinks and carried them over to 201 Duval Street, along with every piece of furniture in the bar and just kept drinking. Easiest move ever!

Address: 201 Duval Street 

Casa Antigua

When Ernest Hemingway first arrived in Key West, he stayed at 314 Simonton Street which is today known as Casa Antigua. Back then the place was The Trev-Mor Hotel, and it housed the island’s first car dealership, Trev-Mor Ford, on the first floor. You could say Hemingway’s love affair with Key West began in this very spot.

When he arrived aboard an ocealiner with his wife in April of 1928, the two of them were expecting to pick up a new Ford and drive back up North. However, the car wasn’t there. Since the car had been delayed and the two were stranded, the car dealer offered them a place to stay at the Trev-Mor Hotel, and over the course of the seven weeks it took for the car to arrive, not only did Hemingway fall for Key West but he also wrote A Farewell to Arms.

Today, Casa Antigua is a private home, but the garden is open for tours, and visitors can glimpse the apartment where Hemingway stayed. They also have a little gift shop called The Pelican Poop Shoppe. Don’t ask me how it got its name.

Address: 314 Simonton Street

Hemingway Days Celebration

Last but not least, if you happen to be in Key West during the month of July, you might find yourself in the middle of the Hemingway Days Celebration. Activities include a look-alike contest for men resembling Hemingway (you’d need a pretty good beard to enter that one!), readings of Hemingway’s work, an exhibit of rare Hemingway memorabilia, a running with the bulls, and a literary competition directed by author and Hemingway’s granddaughter, Lorian Hemingway.

*COOL OPPORTUNITY FOR WRITERS AND HEMINGWAY FANS*

Now, while doing a bit of research about the Hemingway Days Celebration I came across this very cool opportunity.

As part of this year’s celebration, there’s a fiction writing contest happening and the grand prize is 10 days spent writing in Hemingway’s Key West studio!

They’re looking for flash fiction that is 500 words or less, so if this is a dream of yours, you can read more about how to enter here.

Plan Your Own Hemingway Trail: A Field Guide for Fans (and the Hemingway-Curious)

You’ve already covered the greatest hits. Blue Heaven, the house with the six-toed celebrities, the lighthouse across the street, Sloppy Joe’s/Captain Tony’s, Casa Antigua, and the July mayhem of Hemingway Days. If you want to stitch those into a smooth, story-rich day (or two), whilst avoiding the “sprint and forget” shuffle, here’s your guide.

At-a-Glance Itineraries

Half-Day “Best Of” (Walkable Loop)

One Perfect Day (Slow and Satisfying)

Stop-by-Stop Cheat Sheet

The Walking Route

• Start at Blue Heaven. Exit on Thomas St, turn right toward Petronia St for a quick Bahama Village wander, then stroll two blocks east to Whitehead.
• Turn right on Whitehead: Hemingway Home (right) and Lighthouse (left) are directly opposite each other.
• Continue north on Whitehead to Southard, then east to Duval; left on Duval for Sloppy Joe’s (Duval & Greene).
• For Captain Tony’s, go one block west on Greene.
• Casa Antigua is 3 blocks north and 1 block west (Simonton & Eaton).
• To finish at the Seaport, continue north on Simonton to Caroline, right to William St and the Harbor Walk.

Total distance: ~1.7 miles (2.8 km). Flat, but plan shade breaks.

What to Order (and Why)

Getting Around (Simple, Cheap, and Less Sweaty)

One Last, Very Hemingway Thing

He worked in the morning, fished in the afternoon, gathered with friends in the evening, and lived with a foot in the ordinary—cats, boxing, errands—and a hand reaching for sentences. Build your Key West day the same way: a little work (journal), a little water (seaport or swim), a little gathering (music and a drink), and something wonderfully ordinary (a quiet walk through Bahama Village under a sky that looks like it was painted for you).

If you craft your visit with that rhythm, you won’t just see Hemingway’s Key West—you’ll feel why he stayed.

Many thanks to The Florida Keys and Key West for hosting me during my visit. For more travel inspiration have a look at their Instagram, Facebook and Twitter accounts. 

Are you a fan of Ernest Hemingway’s works?