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by Aidan Booth January 18, 2019 4 min read

When Ernest Hemingway and his second wife Pauline Pfeiffer arrived in Key West in 1928, they had no intention of staying long-term. Indeed, the couple only traveled here to pick up a Ford Roadster that Pfeiffer's uncle bought for them. Had the shipment of that car not been delayed, it's possible one of America's finest writers wouldn't have fallen in love with Florida's southernmost city. 

Because Ernest was forced to stay in Key West, he spent a great deal of time exploring the area. The great writer soon made friends with the locals, many of whom affectionately nicknamed him "Papa." For about ten years, Ernest worked, fished, and enjoyed life in Key West, and residents celebrate their most famous literary resident by preserving his home and artifacts as well as hosting a world-renowned festival. 

Anyone interested in taking a relaxing and educational holiday should consider adding a Key West trip to their travel plans 2019. Below, you'll learn about all of the must-visit destinations related to one of the 21st century's greatest writers. 

"Papa's" Key West Pad

One of the most popular travel destinations in Key West is Hemingway's House & Museum, which is located at 907 Whitehead Street. Amazingly, the same wealthy uncle that gifted Ernest & Pauline the new Roadster was generous enough to buy the couple this elegant house in 1931. 

Originally constructed in 1851, the architecture of this house has a distinctly Spanish flair. Ernest and Pauline invested a great deal in giving this historic home a renovation, complete with a very expensive in-ground swimming pool. Be sure to look for a penny that's stuck in the cement near the pool. So the story goes, Ernest threw this penny into the drying cement as he yelled, "Here, take the last penny I've got!" 

As you tour the interior of this house, you'll find everything as it was right before Ernest left Key West for Cuba in the 1940s. Some of the most fascinating finds inside this museum include trophies from Africa, European artifacts, a urinal/fountain (more on that in a bit), and dozens of six-fingered cats. 

Yes, "Papa" was most definitely a cat man. Apparently, a local fisherman gave the author his first polydactyl cat and, well, the rest is history! Ernest immediately started breeding these cats in Key West and at his home near Havana. Today, however, only the Key West museum has a living community of polydactyl felines. 

Anyone can visit this home & museum for a 30-minute guided tour between 9AM – 5PM any day of the year. These tour tickets cost $14 for one adult and $6 for children between the ages of 6 and 12. 

Waiting For The Roadster: The Trev-Mor Hotel

As mentioned in the intro, Ernest and Pauline initially visited Key West to pick up a Ford Roadster. You may be wondering, where did they stay while they were waiting for their car? Answer: the Trev-Mor Hotel at 314 Simonton Street. 

Interestingly, this hotel was located above the Ford dealership. The owner of the dealership allowed the couple to stay in this second floor hotel while they were waiting for their car to arrive. It's in this hotel room that the great author wrote significant portions of his classic WWI novel A Farewell To Arms. 

Unfortunately, you can't visit this room because the Trev-Mor Hotel is now the Casa Antigua residential area. You can, however, purchase a ticket to walk through the atrium garden. 

Sloppy Joe's Or Captain Tony's? You Decide!

Whether he was in Paris, Havana, or Key West, Ernest spent a great deal of time at his favorite bars. In Key West, the author's bar of choice was clear: Sloppy Joe's. However, there are two bars in Key West that constantly compete for the title of the real Sloppy Joe's. 

Originally, Joe Russell (aka "Sloppy Joe") owned the location at 428 Greene Street, but he decided to move to 201 Duval Street in 1937 for financial reasons. Today, the bar on Greene Street is called Captain Tony's Saloon and the one on Duval Street has the famous Sloppy Joe's name. In truth, Papa spent the majority of his Key West time in the Greene Street location, but he did also frequent the Duval Street bar after Russell moved. 

There are pros and cons to choosing between these bars. While Sloppy Joe's owns and displays many of Hemingway's personal belongings, some tourists complain that it's too, well, touristy. Captain Tony's has a more relaxed feel, but don't expect to find as many artifacts here. The only way to figure out which bar suits your style is to visit both! 

Oh, before we forget, here's the story about the urinal mentioned earlier: Hemingway thought he pissed so much money away at Sloppy Joe's that he stole the urinal from the bar one night. That urinal was then converted into a fountain at the writer's Key West home. 

Grow A Beard And Enter Key West's Look-Alike Contest

Even if you've never been to Key West, you might've seen Sloppy Joe's Restaurant on TV around July 21st. Yes, this is where all the bearded men travel to compete in the famed Hemingway look-alike contest! 

To commemorate the celebrated author's birth, Key West locals put on a very special multi-day festival every July. In addition to a look-alike contest, there's also a "Running of the Bulls," numerous sporting competitions, and live readings. If you can, definitely book your trip during this especially festive time of year. 

Key West: An Unforgettable Florida Getaway

Even if you're not interested in literature, don't write off Key West as a possible 2019 travel destination. There are plenty of other fascinating places to explore like the Key West Lighthouse, Fort Zachary Taylor, and President Truman's Little White House. Besides historic sites, Key West boasts some of the finest seafood in the nation. So, go ahead; voyage to Key West in 2019…and save plenty of room for some mouthwatering key lime pie!


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