Key West: Beyond the Bars + Spring Breakers

Before 1930, Key West was the wealthiest city in the United States. After being hit especially hard by the depression, it was one of the poorest. In an effort to revive the town, Julius F. Stone Jr. (head of Federal Emergency Relief Administration at the time) launched a federal grants program that encouraged artists to come to the Southernmost point and, in turn, attracted tourists. Since then, Key West has exuded creativity and eccentricity and remains a wonderful place to spend time.

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Fruit Stand on Duval St.
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A typical scene on Duval St.

My first move upon arriving in Key West was to wander down Duval Street, the notorious epicenter of the city, and take in the sights. I made sure to stop at Sloppy Joe’s bar to pay tribute to Hemingway, a regular of this watering hole during his day. Ernest Hemingway lived in Key West from 1931-1940 with his second wife, Pauline Pfeiffer. The Hemingways purchased a run-down home that had once been the dwelling of Asa Tift,  a wealthy shipwreck salvager who built the residence in 1851. Hemingway and Pfeiffer turned the home into their private oasis, but their presence was so popular in the Keys, they famously had to build a brick wall around the grounds to keep out gawkers.

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The structure of the house was constructed from limestone dug from the ground beneath. There is a beautiful wraparound porch on the second floor, and Hemingway had a walkway constructed from the porch outside his bedroom door to his studio in the carriage house. The legendary author woke up every morning at 6am and crossed the walkway to begin his daily 8 hours of writing. Hemingway was most prolific during his time in Key West, producing 70% of his oeuvre during those 9 years.

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House 2

One of the most eye-catching elements of the house is the gorgeous 60-foot pool. Pfeiffer, wanting to surprise Hemingway while he was traveling as a war correspondent during the Spanish Civil War, commissioned the pool to be built in 1937. The pool was the first in Key West and the only one within 100 miles. Naturally, it was an expensive project. Pfeiffer dropped $20,000 on the construction, or roughly $800,000 in today’s equivalent. For even more perspective, the Hemingways originally bought their home for $8,000.

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After learning of the expense upon his return, Hemingway became enraged and criticized Pfeiffer for her irresponsible spending. Despite his burnishing success, Hemingway always seemed strapped for cash. In a fit of rage, the author pulled a penny from his pocket, declaring “Pauline, you’ve spent all but my last penny, so you might as well have that!”, and nailed it into the bricks of the pool’s patio. The penny is still in place today, protected beneath a glass covering. 

The infamous penny

I enjoyed seeing Hemingway’s dwelling, and especially where he worked while he was in Florida. His study was the birthplace of so many important works of 20th century literature, and is almost perfectly preserved. You also get a sense of his work ethic and routine while you tour the house.

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Hemingway’s Study

In addition to Hemingway’s home, Key West boasts many galleries and public art displays. Two notable galleries are less than a block apart. The first, Coco & Salem, sells wonderful little sculptures called “Square Groupers.”  The history of this term is fascinating. During the 1970s and 1980s, marijuana smugglers would come to the US via the Keys with bails of marijuana on their boats. If the coast guard or police would approach, the smugglers would throw the bails overboard so they weren’t caught with the contraband. These bails would often times be reeling in accidentally by fishermen or wash up on shore, and became known as “Square Groupers.” The little statues are perfect for the Keys with their vibrant colors. They also make for a great conversation piece. If you take the stand off each one, a secret storage place is revealed! 

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My favorite gallery in the city, Key West Pottery, is located at the South end of Duval street on the corner of Catherine. The founding artists at this gallery, Kelly Lever and Adam Russell, are potters who make dazzling examples of clay vases, bowls, sculptures and smaller decorative items. They also design prints, t-shirts and other works of art in various mediums. Their creations are stunning and, best of all, incredibly reasonable price-wise. They are striking, quality pieces that would work in any home, but are especially suited to a tropical aesthetic. On certain days, you can see the artists at work in the studio, and they are also available for commissions by request!

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There are many other galleries located throughout the city, and a fair amount are concentrated by Mallory Square. Be sure to stick around for the legendary Sunset Celebration – a uniquely Keys occurrence!

Apart form the galleries, just wandering around the city of Key West is inspiring. It is such a vibrant, colorful place with endless restaurants to try, bars to frequent and fun to be had. Learn more here

And finally, I am by no means a travel blog, but if you are planning a trip to the Southernmost point anytime soon, I highly recommend looking into the following:

Restaurant: Louie’s Backyard  — The best limeade and conch chowder I’ve ever had!

Accommodations: The Gardens Hotel — amazing location, service, and charm. Feels like you’re a million miles away. 

1 of 2 pools at The Gardens
Front of the hotel: Beautiful Key West architecture