With all due respect to New Orleans, Key West is the best party town in the United States. 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 you can try.
Sloppy Joe's, founded in 1933 and in its current location since 1937, was a one-time hangout for Ernest "Papa" Hemingway and his "mob" and is still one of the most popular and reliably entertaining bars in Key West. Sloppy Joe's 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 choose from 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 veranda, which is lined with stools so visitors can enjoy both a cool drink and the street scene below.
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 will likely 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—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. Capt. Tony's has live music nightly.
As the name implies, this is a tiny bar. Maximum legal occupancy can't be more than about 10. There are 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. It's adjacent to the Smallest Bar Inn.
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.
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 in the business district at 500 Duval St., 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. It's worth a stop for any visiting Parrothead or if you just want to soak up some of the good-times vibe.
Local bars always get the nod on "best" lists, but the Key West outpost of the Hard Rock Cafe chain is an exception 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 alfresco in the house's palm-shaded former front yard.
Located at Key West's historic harbor, the Schooner Wharf Bar caters to boaters as well as tourists. A sunset cruise followed by Dark 'n' Stormy cocktails on the deck here is close to heaven.
The Rum Bar at the Speakeasy Inn on Duval Street is presided over by Bahama Bob Leonard, a laid-back Key West icon who also happens to be one of the premier rum experts in the world. Classic tropical cocktails like the painkiller, mojito, and rum runner are hand-crafted with care at this in-the-know spot for rum aficionados, and Leonard can also introduce you to hidden gems among his vast collection of rums from the Caribbean and beyond.
This seaport bar and restaurant has a great upstairs patio and famous Friday night turtle races—a "where else but Key West?" happening.
The Green Parrot is a fun corner bar that's a must-stop on the walk to or from a visit to the Hemingway home. Lots of locals, as well as wandering tourists, drop in here. Checking out the signs, memorabilia, and assorted junk hanging around the bar is worth popping in for a cold one.
This Duval Street Irish bar includes weekly live performances by Irish Kevin himself, an immigrant who settled in Key West in 1992 and opened a pub on Duval Street.