Make Papa Proud: How to Live Like Hemingway in Key West

Do you bear a striking resemblance to Papa Hemingway? Let the judges decide! (Photo: Courtesy of Sloppy Joe’s)

“When you stop doing things for fun you might as well be dead.” – Ernest Hemingway, True at First Light

The Key West beach lifestyle is so legendary that it even tempted iconic American writer Ernest Hemingway to live, write and party hard here.

Whether you’re a lover of his works or are inspired by the Clive Owen and Nicole Kidman film, Hemingway & Gellhorn, Key West makes for the perfect Hemingway-inspired getaway.

Why search for this Nobel Prize-winning author in Key West? Because his spirit is stamped across the island, and Hemingway was all about living life to the fullest. Now it’s your turn to create your very own “Hemingway moments.”

Is it time to finally learn to scuba dive, sail or simply live life out loud for a long weekend?

In Key West, there’s no shortage of drinking, eating and sleeping establishments to make your stay unforgettable.

Drink Like Hemingway

Hemingway was known for meeting up with his drinking buddies daily in the late afternoon at high-class-yet-low-brow hotel bars and other drinking holes.

Some Key West hotels even boast Hemingway not only drank at their bar, but also slept under their roofs. Though Hemingway wasn’t a visitor to the modern Key West Marriott Beachside Hotel located on the waterfront, it’s still a great option for enjoying casual drinks and appetizers by the pool.

And if you’re going to act like Hemingway during your visit, then you should know Key West holds a Hemingway® Look-Alike Contest each year in July.

Tied to the popular Sloppy Joe’s bar on Duval Street, this three-day festival to all things Hemingway (or “Papa,” as he was known in his later years) even includes tributes from celebrities such as TV chef Paula Deen’s husband Michael Groover, who showed up to the 2012 gray-bearded contest.

Eat Like Hemingway & Visit His Home

Want to eat like Hemingway? Walk down to Pepe’s Café (806 Caroline St.) for the fresh-from-the-sea, “Pepe’s style” catch of the day. The ramshackle café is the oldest dining establishment in Key West.

Its funky outdoor patio attracts those who want to chill out and enjoy the best tastes of the Key West beach lifestyle for breakfast, lunch and dinner.

Take a trolley tour for even more Hemingway lore. Trolley passes are usually good for two days of hopping on and off at 12 Key West stops, including Hemingway’s home (907 Whitehead St.).

Hemingway resided in his island home for 12 years and he wrote some of his most famous works right here. While you won’t see Papa here today, you can meet a few six-toed cats descended from his own cat, Snowball.

Sunset Cruising Like Hemingway

It may not be gritty like Hemingway’s fisherman in Old Man and the Sea, but a sunset cruise in Key West is certainly memorable.

Some even feature wine aficionado crew members who pour wines paired with European-style plates of cheese, nuts, crudités and seasonal fruits. Sounds like a lot more fun than struggling with a huge marlin, right?

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