4 Places to See Hemingway History in Key West

One of the best-known former residents of Key West is the author Ernest Hemingway. If you’re in Key West, you’re likely to come across more than a few places touting their relationship to the writer. Here are four (or five) places in Key West where you can see Hemingway history in person.

1. The Hemingway Home

Located at 907 Whitehead Street, the home where Hemingway lived for most of his time in Key West is a tourist destination, with tour groups coming through all day, every day. The home itself is beautiful both inside and out. If you visit, don’t forget to check out the cats who make the place home – they descend from a cat owned by the author and are known for being polydactyl, which means they have extra toes.

2. Sloppy Joe’s and Captain Tony’s

Hemingway’s love for alcohol is legendary. In Key West, he could regularly be found on a barstool at Sloppy Joe’s, a bar owned (at the time) by his friend Joe “Josie” Russell. You can still visit Sloppy Joe’s today, at the corner of Duval and Greene Streets. However, for at least part of the time when

Hemingway lived in Key West, Sloppy Joe’s was located down the street from its current location, where the bar Captain Tony’s now sits on Greene Street. The bar moved on May 5, 1937, when patrons at the old Sloppy Joe’s literally picked up the furnishings of the bar and moved them down the street to the new (and current) location, in return for a free round of drinks.

3. Hemingway’s First Key West Home

Although the Whitehead Street home is the one most associated with Hemingway on the island, his first home was at 314 Simonton Street. When Hemingway lived there, this was the island’s Ford dealership. Hemingway lived above the dealership, and it is here that he finished the first draft of one of his classic novels, A Farewell to Arms.

4. Blue Heaven

One of Hemingway’s favorite sports was boxing. When in Key West, he could regularly be found attending amateur boxing matches or refereeing them himself. During his days in Key West, Hemingway would often find his way to the property at 729 Thomas Street to referee boxing matches in the courtyard. Today, this property is a popular restaurant known as Blue Heaven, and you can have a meal in the courtyard where Hemingway once participated in one of his favorite sports.