Inside Hemingway’s Key West: Best Places to Visit for Fans

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There is no doubt the in my my mind that the natural beauty, historical charm, and the laid-back lifestyle of Key West fueled Ernest Hemingway’s creative genius. Hemingway found inspiration from his interactions with the colorful characters of Key West—fishermen, bar owners, and locals. Continue reading for three things to see in Key West.

Hemingway House

The Hemingway House and Museum is a must-see if you are in Key West. The house was built in 1851 and purchased by Hemingway’s father-in-law for $8,000. You can walk through the house and the gardens, but the only place “off-limits” is Hemingway’s writing room. You can only view it through a screen.

Another interesting feature the grounds are home to nearly 60 polydactyl cats. The cats are descendants of Hemingway’s original six-toed cat, Snow White. These cats, named after famous figures, come in various shapes and sizes and are well cared for and drink water out of wine classes scattered across the property.

Southernmost Point

The Southernmost Point Buoy has been a popular tourist attraction since 1983, drawing crowds eager for a photo op. While it claims to mark the southernmost point in the continental U.S., that’s not entirely accurate—but that doesn’t stop visitors from lining up. On a busy day, expect to wait at least 15 minutes for your turn in front of this iconic landmark.

Sloppy Joes Bar

Hemingway’s time at Sloppy Joe’s in Key West had a lasting impact on both his life and his writing. The bar became his regular hangout, where he and his “Mob” of literary friends would drink, debate, and inspire one another.

The Hemingway Look-Alike Contest in Key West is a lively annual event that celebrates the life and legacy of Ernest Hemingway through playful competition and spirited festivities. Contestants from around the world dress as Hemingway, competing not just for physical resemblance, but for capturing his bold spirit.

Key West’s charm, history, and quirky characters clearly left their mark on Hemingway. Exploring these spots is like stepping into his world—where creativity, adventure, and a little bit of mischief were always on the agenda.

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