Where Ernest Hemingway Ate and Drank in Key West

I’ve always believed you don’t just visit Key West. You drift into it, sun-dazed and salt-streaked, until the island starts to feel like memory. Perhaps that’s why prolific author Ernest Hemingway never really left when he moved away in 1938.

His stories linger in the Conch Republic. You’ll find his presence in the salty breeze, in the chipped bar tops, and in the rhythm of a town that feels like a slice of paradise from a bygone era.

I felt an immense wave of nostalgia when I stood inside his home on Whitehead Street. I felt it again years later in Cuba at his former home, Finca Vigía, stepping onto his pool deck just across from his beloved fishing boat, Pilar.

My Personal Connection to Hemingway

As a first-generation American of Cuban descent and a Miami native, tracing his footsteps between Key West and Havana is extra special. He moved between the islands, chasing stories, embracing strangers, soaking up the sea, and, of course, having a drink at the end of the day.

Finca Vigía, located in San Francisco de Paula, 14 miles from Havana, was Hemingway’s home from 1939 to 1960. Now a national museum (Museo Hemingway), the Spanish-colonial home remains filled with his original belongings, books, and art. It’s also home to his fishing boat, Pilar. He wrote The Old Man and the Sea here. I was lucky enough to visit in 2014, when things were stable on the island.

However, some of his most meaningful days weren’t in Cuba. They occurred a decade before, down in the magical town of the Conch Republic.

Hemingway Calls Key West Home

Before his time in Cuba, Hemingway made the Southernmost City his home. Hemingway arrived in Key West in 1928, after his time in Paris. Those years, from 1928 to 1938, would later be called the “best decade of his life.” He wrote in the mornings, fished in the afternoons, and drank at night with a cast of characters that felt pulled straight from his own novels.

Pretty much anyone who knows anything about Key West knows that Hemingway once called the island home. He is arguably the most famous Key West resident of all time, hence the huge annual Hemingway Days celebrations held in his honor each July. (I experienced the annual Hemingway Look-Alike Contest in 2025, and I highly encourage you to make the trip, as well.)

In the 1930s, when he resided on the island, Hemingway, whom locals affectionately called “Papa,” became a major tourist draw. People were constantly trying to get into his home just to catch a glimpse of the famed author. Nearly a century later, that same pull still exists. His presence lingers in a way that feels almost tangible.

Visiting His Favorite Key West Spots Today

Some of the places Hemingway once frequented no longer exist, and others have quietly become private residences. However, there are still plenty of spots across Key West where his spirit feels alive, where you can walk the same streets, step into the same bars, and experience a version of the island that hasn’t entirely changed.

Below are some of those places, listed alphabetically, where you can still follow in his footsteps.

Casa Antigua (Formerly the Trev-Mor Hotel)

In April 1928, Ernest Hemingway arrived in Key West by ocean liner with his wife, Pauline, after several years in Paris, expecting nothing more than a brief stop to pick up a Ford he had ordered. The plan was simple: grab the car and drive up the Keys. But the car didn’t arrive. Instead, the couple found themselves unexpectedly stranded, taken in by the owners of the Trev-Mor Ford Agency and given a room upstairs while they waited. The car dealership was on the first floor, and hotel rooms were on the upper two floors.

What was supposed to be a short stay stretched into weeks, and in that time, something shifted. From their window, Hemingway could look out over the seaport, wander down to Mallory Square in search of fishing charters, and settle into a rhythm that felt instinctively right. He wrote in the mornings, explored in the afternoons, and by night, made his way to the bars that would soon become legend.

It was during this accidental pause that he penned A Farewell to Arms from his second-story room, unknowingly anchoring himself to the island in a way that would define the next decade of his life.

That first stay unfolded at what we now know as Casa Antigua, formerly the Trev-Mor Hotel at 334 Simonton St. It’s easy to walk past today without realizing its significance, but this was Hemingway’s introduction to Key West, the place where he first lived, wrote, and fell hard for the island. He and Pauline remained there for nearly two years before moving into their permanent home on Whitehead Street, but the foundation of everything began here. 314 Simonton St, Key West; keywesthistoricmarkertour.org.

The Green Parrot (Formerly Brown Derby)

The Green Parrot Bar, the oldest bar in Florida, dating back to 1890, is a true Key West institution with a soul as colorful as the island itself. It was originally a grocery store before becoming the Brown Derby sailors’ bar.

At Brown Derby, you can imagine Hemingway tucked into a corner, watching everything. At the former Sloppy Joe’s (Cap’t Tony’s Saloon) and Green Parrot, he surrounded himself with what locals called “The Mob.” Fishermen, bartenders, writers, drifters. People who lived fully and loudly. They drank, they fished, they became characters. And then they became literature.

The bar transformed in the 1970s when visionary owner Judy Sullivan turned it into one of America’s “great freak-bars,” attracting hippies, bikers, and free spirits with its open-air shutters and legendary tequila specials. Later, owners Jim and Linda Bean cemented their legacy by making live music the bar’s heartbeat, earning national recognition from Playboy in 2000 as one of “The Best Bars in America.”

Today, under the stewardship of John Vagnoni and Pat Croce, the Green Parrot remains a rowdy, welcoming corner saloon where locals and tourists gather for free, old-school popcorn, the famous “Root Beer Barrel” shots (I personally am not a fan, but you gotta try it at least once), and unforgettable nights of music and memories.601 Whitehead St., Key West; 305-294-6133; greenparrot.com.

La Concha Key West (Formerly Key West Colonial Hotel)

In April 1928, when Hemingway arrived aboard a ferry from Cuba, the hotel was his first glimpse of downtown. The light pink, seven-story hotel was later referenced in two short stories. Plus, it’s referenced in his 1937 novel, To Have and Have Not.

Known as the Key West Colonial Hotel in Hemingway’s time, it became a gathering place for visiting friends and family. He and Pauline spent time here socializing and staying connected to people passing through the island.

Celebrating its 100th birthday in 2026, La Concha Key West holds a special place in my heart. It’s a landmark Old Town hotel I love for its Art Deco glamour, Cuban heritage, rooftop views, and unbeatable location.

Plus, you’ll find welcoming staff, a lively pool, a gorgeous wooden bar, and a one-of-a-kind seashell-inspired breakfast dining room. 430 Duval St.., Key West; 305-296-2991; laconchakeywest.com.

The Waters Surrounding Key West

This might be the most important “place” of all. Hemingway lived for the water. He fished these seas relentlessly, chasing marlin and meaning in equal measure. He even used the Pilar to patrol for German submarines during World War II. You can still head out on a fishing charter today and get a glimpse of what that life felt like, wind in your face, nothing but blue in every direction.

Or, you can feel his presence on the docks themselves, where the line between bar and ocean disappears. Fishing wasn’t separate from drinking for Hemingway. It was part of the same ritual.