The 5 Hotels in the Florida Keys Where Ernest Hemingway Probably Got Really Drunk At

Jill Martin | January 22, 2018

Like a straw in a daiquiri, Key West and Ernest Hemingway proved to be a beneficial paring. He not only found inspiration on this island, he found love. He also penned intriguing words about Key West in novels, promoting its uniqueness to the world. So it’s no wonder that Key West loved him back, and to this day, celebrates him each summer during Hemingway Days. Although mostly documented, we’ve taken a few creative freedoms in listing properties where you can do more than walk in his shoes, you could experience sights, sounds, and flavors, similar to those that captured his imagination. Enjoy a drink at one of these famous Key West bars. Cheers.


Casa Marina, A Waldorf-Astoria Resort

Why it made the list

Although he may have missed the New Year's Eve grand opening in 1920, Hemingway’s time in Key West throughout the 1930s, and subsequent visits, makes for good theory that he knocked back a few behind these exclusive doors. Perhaps in the 1940s when it was used as officer’s quarters for the Navy during WWII, or in the 1950s when it was a hot spot for celebrities.

If you’ve got the money, honey, this resort delivers. Histor Read More


Captain Pip’s Marina & Hideaway

Why it made the list

Less than an hour north of Key West, Captain Pip’s is low key, unpretentious, and the kind of place where you can blend in with the crowd for days, or nights. No wonder it boasts a list of infamous guests, like Hemingway, and even Jimmy Hoffa. We can imagine him at the dockside bar, chatting it up with salty, seafaring captains, and comparing fish tales of yore.

If you love old school-style Florida resorts, this is the re Read More


La Concha Hotel & Spa

Why it made the list

Key West’s tallest hotel, and one of the most luxurious of its time, was frequented by Hemingway in the 1930s. He not only wrote about La Concha in his novel, To Have and Have Not, he began writing it here. And he frequently checked in with the woman who’d become his third wife (while married to his second). Some say he still haunts the suite that bears his name. While the rooftop bar is gone, you can still toast him at their lobby bar and restaurant, 430 Duval.

Historic properties always have their quirks, and La Concha Read More


Why it made the list

First a judge’s home in the late 1800s, then an illegal speakeasy in the 1930s, this colorful and historic hotel is rather famous for its frequent visits from Hemingway. He could walk here in under 12 minutes (and stumble home in 20). In 1939, it became a Cuban nightclub, and knowing his love for Havana, we image he salsa’d his nights away after imbibing in plenty of liquid courage.

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Speakeasy Inn

Why it made the list

This beloved inn is the former home of famed rumrunner, Raul Vasquez. Purchased in 1920, locals back then knew this was the place for Cuban rum, cigars, and a potentially lucrative game of cards. It’s also a mere 7-minute walk from the Hemingway Home, and as much as Ernest enjoyed a good daiquiri, we bet he wandered over frequently to double down.

Romantic and historic, this fully restored inn sits on the m Read More

  • 5. Casa Marina, A Waldorf-Astoria Resort
    1500 Reynolds St.,Key West,Florida,USA,33040
  • 3. La Concha Hotel & Spa
    430 Duval St.,Key West, Florida,USA,33040
  • 1. Speakeasy Inn
    1117 Duval St.,Key West,Florida,USA,33040

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