With all due respect to New Orleans, Key West is the best party town in the U.S. The weather is great, the people are friendly, the drinks are generous and cheap (especially at Happy Hour), and the atmosphere is safe and fun. You can't possibly drink in all of Key West's bars in one night or even two ... but some people try. My picks for the best bars in Key West include:
Sloppy Joe's, founded in 1933 and in its current location since 1937, was a one-time hangout for Papa Hemingway and his 'mob' and is still one of the most popular and reliably entertaining bars in Key West. Sloppy Joes is usually busy even on a Monday night in the off-season, and the large stage attracts the best bands playing in Old Town -- the music keeps going until 2 a.m., and the high ceilings allow for decent acoustics. Come in the late afternoon to dodge the crowds, or pop into Joe's Tap Room to enjoy a variety of draft beers on tap.
The low-slung and partly hidden Hog's Breath Saloon retains the feel of a biker bar despite its obvious appeal to the Key West tourist trade -- patrons can (and often do) dismount their Hogs and amble up to a stool at the open-sided bar. In typical Key West tradition, live bands and bikini contests dominate the entertainment calendar, and it's almost required that visitors leave wearing a Hog's Breath t-shirt emblazoned with the saloon's famous motto: "Hog's Breath is Better than No Breath at All."
The Bull and Whistle is really two bars in one (three, if you count the rooftop Garden of Eden). The ground-level Bull is dominated by a large central bar with a small performance stage in the corner, while the second-floor Whistle is more of a sports bar with a pool table, darts, and other bar games. The best aspect of either is unquestionably the Whistle's narrow second-floor verandah, lined with stools so visitors can enjoy both a cool drink and the street scene below.
The Garden of Eden
Perched atop the Bull and Whistle is Key West's only clothing-optional bar, the aptly named Garden of Eden. How much skin can you expect to see at this rooftop bar, lined with tropical plants and shielded from prying eyes below? From a lot to not much at all, depending on what day you come, what time it is, and what the weather is like. At a minimum you may have a topless bartender (serving drinks that run a bit more expensive than elsewhere in town or even downstairs) and a few dirty dancers, but come on a sunny afternoon and you'll find nude sunbathers reclining on lounge chairs. You don't have to go nude here, and body paint is a good way to be a bit daring without showing too much, but the no-photography rule is strictly enforced.
The site of the original Sloppy Joe's -- which moved across the street in a spat over rent -- this was Hemingway's Key West hangout for many years and retains a wealth of local history, much of it hanging from the walls of the bar. That tree you might be leaning against with your drink, for example, was Key West's 'hanging tree' in the 19th Century, so your companions could include the ghosts of some pirates who had their necks stretched by local vigilantes. Located on Greene Street, Captain Tony's has live music nightly.
The rooftop bar at the Rum Barrel restaurant, located next door to the Key West Pirate Soul Museum, is a nice spot to have a Happy Hour drink (many of the well drinks are prepared with top-shelf liquors) and enjoy the sunshine and enjoy some live music by solo performers on the small stage. Owned by a Philadelphia transplant, the bar also is home to the local Eagles fan club and proffers an authentic Philly Cheesesteak -- with or without "wiz."
The Smallest Bar
Like the name implies, this is a tiny bar. I'm not sure what the fire code says about maximum occupancy, but it can't be more than about 10. There's only about three barstools, but it's a great place to take over with a (small) group of friends, and there's plenty of interaction with curious passers-by on Duval Street.
The mechanical bull is the star of the (sometimes raunchy) show at Cowboy Bill's, and the bar has a friendly atmosphere even if you hate country music and line dancing (which you'll have to endure if you stop in). You have to love the saddle barstools. The 'Southernmost Country Bar' also has a whiskey bar and nightly Pabst Blue Ribbon special for y'all.
I don't like to include chain restaurants on lists like this, but I'll make another exception for the Key West outpost of the Hard Rock Cafe chain because of the loving way that the owners have restored a beautiful, three-story Victorian home in the heart of Duval Street. Ogle the rock memorabilia and drink a toast to your heroes on the balcony or al fresco in the house's palm-shaded former front yard.
This isn't the biggest or even the best of Jimmy Buffett's Margaritaville chain of bar/restaurants -- but it was the first, opened in 1985. Located behind a pink facade at 500 Duval St. (in the business district), Margaritaville Key West has a stage for bands and the usual tiki-bar decor, as well as a full menu of dining and specialty drink options. Worth a stop for any visiting Parrothead or if you just want to soak up some of the good-times vibe.