The 12 Best Bars in Key West

Duval street, Key West, Florida, USA at night

Travelpix Ltd / Getty Images

With all due respect to New Orleans, Key West is probably 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.

01 of 12

Sloppy Joe's

Sloppy Joe's
201 Duval St, Key West, FL 33040, USA
Phone +1 305-294-5717

Sloppy Joe's, founded in 1933 and in its current location since 1937, was a former 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.

02 of 12

The Hog's Breath Saloon

400 Front St, Key West, FL 33040-6617, USA
Phone +1 305-296-4222

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."

03 of 12

The Bull and Whistle

Bull & Whistle
Richard Elzey/Flickr/Creative Commons
224 Duval St, Key West, FL 33040, USA
Phone +1 305-296-4545

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. This three-for-one special features daily live music as well as amazing art—"The history of Key West, its icons, and the events that make up the magic of the island are hand-painted along the walls," the company states on its website.

04 of 12

The Garden of Eden

Garden of Eden at Bull & Whistle Bar

Courtesy of the Bull & Whistle Bar

224 Duval St, Key West, FL 33040, USA
Phone +1 305-296-4545

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.

Continue to 5 of 12 below.
05 of 12

Capt. Tony's Saloon

Capt. Tony's Saloon
Sam Howzit/Flickr/Creative Commons
428 Greene St, Key West, FL 33040, USA
Phone +1 305-294-1838

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.

06 of 12

The Smallest Bar

Smallest Bar
Roger W/Flickr/Creative Commons
124 Duval St, Key West, FL 33040, USA

As the name implies, this is a tiny bar. The room itself is 72-square feet (about the size of a jail cell), making maximum legal occupancy no 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. This miniature bar is across the street from the Smallest Bar Inn, a very normal sized hotel.

07 of 12

Margaritaville Key West

Jimmy Buffetts Margaritaville
1Photodiva / Getty Images
500 Duval St, Key West, FL 33040, USA
Phone +1 305-292-1435

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. You can try some locally-inspired dishes for a quick eat, like conch fritters and a slice of delicious key lime pie. You can get their specialty drinks in either a regular 22 oz. glass, or in a souvenir blender cup. Specialty drinks are pricey at about $18 a glass but are made with a lot of different and delicious liquors and juices. It's worth a stop for any visiting Parrothead or if you just want to soak up some of the good-times vibes.

08 of 12

Hard Rock Cafe Key West

hard Rock Cafe
qwesy qwesy/Wikimedia Commons
313 Duval St, Key West, FL 33040, USA
Phone +1 305-293-0230

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. The brand is embracing their found home well; on their website, they talk about a potential spirit wandering their halls. At this Hard Rock Cafe, you can ogle the rock memorabilia, drink a toast to your heroes on the balcony, relax on alfresco in the front yard, or try to catch a sighting of the restless spirit of Robert Curry. A little something for everyone!

Continue to 9 of 12 below.
09 of 12

The Schooner Wharf Bar

Schooner Warf Bar
Michael West
202 William St, Key West, FL 33040-6645, USA
Phone +1 305-292-9520

Located at Key West's historic harbor, the Schooner Wharf Bar caters to boaters as well as tourists, including some notable names like Al Jardine from the Beach Boys and the late broadcaster and author, Charles Kuralt. Specialty drinks at this nautical bar include the "Schooner Lemonade," rumrunners, and mango daiquiris. If you're looking for a sweet deal, this bar offers not one, not two, but three different happy hours: the first from 8 a.m. to noon, the second from 5 p.m. to 7 p.m., and the last from 2 a.m. to 4 a.m. A sunset cruise followed by Dark 'n' Stormy cocktails on the deck here is close to heaven.

10 of 12

The Rum Bar

1115 Duval St, Key West, FL 33040, USA
Phone +1 305-296-2680

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 over 350 rums from the Caribbean and beyond.

11 of 12

The Green Parrot

601 Whitehead St, Key West, FL 33040-6548, USA
Phone +1 305-294-6133

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. This eclectic bar has gone through several changes throughout its time but has remained a staple for great music and comradery in the Key West. The walls are decorated with signs, memorabilia, and assorted junk, and most everything has an interesting story or history. This bar is open seven days a week and has live music performances almost daily, from country bands to brass punk rock.

12 of 12

Irish Kevin's

Irish kevin's
 Beachfront Solutions/Flickr/Creative Commons
211 Duval St, Key West, FL 33040, USA
Phone +1 305-292-1262

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. The bar boasts its many beers on tap, and they encourage their guests to sing along with Irish Kevin and their many other performers, and possibly "become part of the show" themselves. Can't make it in to see one of your favorite performers? No worries, you can head to their Stage Cam page on their website and watch the performances live as they happen.

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The 12 Best Bars in Key West