Sloppy Joe's Bar in Key West: Ernest Hemingway's Favorite Hangout

Key West attracts travelers with its warm climate, Caribbean resort atmosphere, and vibrant nightlife. Among the many bars, one place stands out for its history and character. Celebrities have relaxed here, live music has played, and signature cocktails and dishes have become its hallmark.

History and Legends

In 1933, when Prohibition ended in the United States, a small bar opened in Key West, quickly becoming a favorite spot for locals and visitors alike. The establishment was originally located elsewhere, but in 1937 it moved to a building on Duval Street, where it remains today.

One of the most famous patrons was Ernest Hemingway. It is said that he often dropped by to have a couple of glasses of rum and discuss the latest news with friends. Bartenders and regulars still tell stories of his antics. One of them states that the writer loved to hold drinking competitions here, and his six-toed cat sometimes climbed onto the bar counter as if he were a full-fledged regular.

There is a legend that the writer's second wife, Pauline Pfeiffer, specifically chose a house opposite the Key West Lighthouse so that Hemingway wouldn't get lost on his way back from the bar — the lighthouse served as a landmark for him. How true this is is unknown, but the story itself has become popular among tourists.

Over the years, the place has turned into a cult location. Tennessee Williams, Truman Capote, and many others have been here. The atmosphere of freedom and ease that reigned inside attracted creative people and travelers.

During the Cuban Missile Crisis, the establishment even became the unofficial headquarters for journalists covering the situation. It is said that the bartenders knew the latest news before official agencies.

Another legend is associated with underground alcohol supplies during Prohibition. Rumor has it that even before the legalization of the establishment, its owners dealt with smugglers, and boxes of banned rum could be hidden in the building's basements. This story, of course, is not confirmed by anything, but visitors like to believe that the strong walls hide the secrets of the past.

Today, the bar continues to live its life. Both tourists and old-timers who remember the legendary times come here. Some come for the atmosphere, others for the history, and some are just looking for a good place to spend an evening in the company of live music and the right cocktails.

Menu and Signature Drinks

The food here is served without unnecessary complications, but with character. The main hit is the sandwich that gave the establishment its name. The recipe appeared back in the 1930s and has changed little since then. Chopped beef in tomato sauce, a soft bun, a generous portion of filling — a simple but successful combination. It is served with french fries or crispy chips.

In addition to the signature dish, the menu includes burgers, chicken wings, tacos, and fresh seafood. Local fishermen supply mahi-mahi and shrimp, so seafood lovers can take, for example, black grouper tacos or breaded shrimp. There are plenty of options — from classic beer snacks to large portions for those who are hungry after a long walk.

The main pride of the bar is its cocktails. Primarily rum-based. Key West has always been closely associated with this drink, so the selection here is worthy. One of the most popular options is the Rum Runner. It contains light and dark rum, banana and blackberry liqueur, pineapple and orange juices, and a drop of grenadine on top.

Those who prefer something stronger usually take the Hemingway Daiquiri. This is the very cocktail that, according to legend, the writer himself loved. It has no sugar, but it does have rum, lime juice, maraschino liqueur, and a little grapefruit fresh.

For those who want something refreshing, there is the Key Lime Pie Martini — a version of the classic dessert in liquid form. Vanilla vodka, lime liqueur, cream, and a little cookie crumble are mixed in a glass.

Of course, the menu also has classic options — margarita, pina colada, mojito. Beer is also served, both bottled and draft. The establishment focuses not only on cocktails, but also on a good atmosphere, so it's easy to find something to suit your mood here.

Atmosphere and Entertainment

This establishment is noisy, fun, and a bit chaotic — just as a good bar should be. It's rarely quiet here: someone is laughing, someone is ordering another cocktail, and live music plays almost non-stop.

The main entertainment is performances by local musicians. On stage, you can hear blues, rock 'n' roll, country, or something with obvious Caribbean motifs. Often, bands that have been playing here in the evenings for a long time drop by, but there are also spontaneous jam sessions. Guests can simply listen, sing along, or even go to the dance floor — no one will give you a dirty look if someone starts dancing right at the bar.

Inside, the walls are covered with vintage photographs, signs, and various souvenirs left by visitors. Somewhere you can see celebrity autographs, in another corner — yellowed newspaper clippings telling about important events in the history of the place.

There is another tradition — leaving money on the walls and ceiling. Tourists pin bills with signatures or wishes, and over the years they have accumulated so much that they say there are several thousand dollars hanging there in total. No one touches them — it is believed that this brings good luck.

The bar is open from morning until late at night. During the day, tourists come here before a walk around the city or after a long swim, and in the evening those who want to relax a little, have a couple of cocktails and listen to live music gather. The closer it gets to night, the louder it gets in the hall, and the dance floor gradually fills up.

This is a place where you can easily strike up a conversation with a stranger, listen to stories from bartenders, or simply watch the crowd have fun. Some come for an hour, others stay until closing.

Tips for Visitors

Before heading to the bar, there are a few things to consider:

• When to come. During the day, it's quieter and more spacious, and you can get a table without waiting. In the evening, lively fun begins, and by night the hall is completely filled. During the tourist season, it gets so crowded that you have to stand in line.
• Where to sit. Inside — music, dancing and the true spirit of the establishment. If you want to be in the center of events, it is better to choose a place inside. Outdoor tables are suitable for those who want to sit quietly and relax.
• What to order. The signature sandwich is the most popular dish. The portions are large, so sometimes it makes sense to take one for two. In the cocktail menu, you should pay attention to rum drinks. Among the local favorites are Rum Runner, Hemingway Daiquiri and Key Lime Pie Martini.
• How to pay. The bar accepts cards, but it is better to have cash with you. Tips are left at the rate of 15–20% of the bill.

There is no dress code here, but comfortable shoes will not hurt — especially if the evening ends with dancing.

What else to see nearby

The bar is located in the very center of Key West, which means there are plenty of places to visit around. If you have time, you can walk around the neighborhood and look into the iconic points of the city.

• Hemingway Home and Museum. Just a couple of minutes' walk away is the house where the writer lived in the 30s. His personal belongings, study and even descendants of his famous six-toed cats have been preserved here. The tour takes about an hour, but you can just walk through the shady courtyard.
• Key West Lighthouse. Located directly opposite Hemingway's house. The height of the tower is 22 meters, and the upper platform offers one of the best views of the city. The climb is easy, but you should be prepared for narrow steps.
• Duval Street. The main street of Key West, full of bars, shops and restaurants. It stretches from the ocean to the bay, and you can walk along it for hours, going to local shops and souvenir shops. It is especially lively in the evening.
• Buenos Aires Park. A small green corner near Duval Street. Here you can take a breath, relax in the shade of palm trees and admire the statues donated to Key West by the Argentine capital.
• Southernmost Point in the USA. One of the most photographed symbols of Key West is a concrete buoy marking the southern border of the continental part of the country. It is a 10-15 minute walk from the bar to it. If you want to take a photo without a crowd, it is better to come in the morning.
• Mallory Square. A square on the shore, famous for its sunsets. Every evening, street performers, musicians and tourists gather here to see off the sun. A great place to end a walk.

In Key West, everything is close by — from the bar to any of these points can be reached on foot in a few minutes.