Sloppy Joes Bar

Every visitor to Key West ends up at Sloppy Joe's at some point, and it is worth doing properly. The bar opened on December 5, 1933, the day Prohibition ended, run by Joe Russell, a charter-boat captain, rumrunner and fishing companion of Ernest Hemingway, who drank here throughout his Key West years in the 1930s. The original bar was on Greene Street, in the building now home to Captain Tony's Saloon; in 1937, after a rent dispute, Russell moved the business to its current corner at Duval and Greene, and legend says customers carried the bar and the furniture down the street in a single night without missing a drink. The name, supposedly suggested by Hemingway, came from a Havana bar with a reputation for wet floors. Today Sloppy Joe's is a big, open-sided saloon on the busiest corner of Duval, with tall windows thrown open to the street, ceiling fans turning, Hemingway memorabilia on the walls and live music on the stage from around midday until late at night. Entry is free; you pay for the drinks and pub food. The atmosphere is loud, sociable and unmistakably touristy, and that is part of the appeal — it is a rite of passage rather than a hidden gem. The bar is at its most famous each July during Hemingway Days, when bearded men from around the world compete in the Hemingway look-alike contest. Honest caveats: it is crowded on cruise-ship days and in high season, drink prices are what you would expect on the main tourist strip, and the official tourism listing tags it adults-only, so check the policy before bringing children.

The Hemingway connection is the bar's soul. Hemingway arrived in Key West in the late 1920s, and Joe Russell — "Josie" — became one of his closest friends, taking him fishing in the Gulf Stream and to Cuba, and appearing in thinly fictionalized form in his writing. The writer spent many evenings at Russell's bar, which was a working man's saloon with a mixed crowd of fishermen, sailors and locals, and the stories of those years, true and embellished, are told on the walls and by the staff. Captain Tony's Saloon on Greene Street, the bar's original home, is a separate establishment with its own colorful history and makes a natural second stop.

How to enjoy it: come in the afternoon for a seat by the open windows, a cold drink and the best people-watching on Duval, or at night for the full music-and-crowd experience. Afternoon sets are usually acoustic and mellow, while evening bands play to a packed room. The food is straightforward bar fare, including the namesake sandwich. The gift shop does a brisk trade in T-shirts. Pace yourself: the drinks are generous, the afternoon heat is real, and Duval is long, so alternate with water and eat something before the evening crowd arrives. If you are in town in July for Hemingway Days, expect the look-alike contest to fill the bar and the street, and book accommodation far ahead.

Who it suits and pairing: first-time visitors who want a classic Key West bar experience, nightlife seekers on a Duval crawl, and Hemingway fans who have just toured his house. Pair it with the Hemingway Home and Museum on Whitehead Street by day, with the Mallory Square sunset a block away, and with Captain Tony's around the corner. Families and travelers who prefer quiet should enjoy Duval in the daytime instead, or head to the Historic Seaport for a calmer drink by the water. And if the crowd is three deep at the bar, simply walk on; the history is on the walls, and you can come back in the quieter mid-afternoon lull.