A Key West Bar Crawl
Drink like Hemingway in the Conch Republic
When Ponce de Leon stumbled upon a piece of land in 1512, he named it Cayo Hueso, Bone Island. This westernmost island in the Florida Keys —and the Southernmost city in the contiguous United States— has since been a place for smugglers, pirates, poets, artists, bohemians, writers, and tourists who converge on this roughly four-square-mile city to escape from the everyday life of…well…anywhere else.
Key West is like no other city in the U.S. Notable Key West residents have included John James Audubon, Tennessee Williams, and Jimmy Buffett at some point; and Harry S. Truman had a summer house in Key West. Arguably, the most famous resident of Key West was Ernest Hemingway. A young Hemingway wrote “A Farewell to Arms” in Key West when his car broke down in 1928, and stayed for a decade. In between writing some of the greatest works of contemporary American fiction, Hemingway managed to drink…a lot. Walk into almost any bar and you’ll be regaled with “Hemingway drank here” signs — even if the bar opened just a few weeks ago.
Nevertheless, most of the bars in Key West still speak to the artist in all of us — they’re colorful, spiritual, and funky. Some are haunted, and yes — some were actually frequented by Hemingway.
The best part about Key West is that it’s easy to visit many great bars in one day and stumble back to your bed and breakfast (don’t drive — or even bike if you’re planning some day drinking). Most bars are within walking distance from each other on the island’s main drag — Duval Street. And, although there are dozens of bars to choose from, here are the most interesting and iconic bars you should check out on your Key West bar crawl.
Though Sloppy Joe’s is the home of the Hemingway lookalike contest, held annually on July 21 on Hemingway’s birthday, Captain Tony’s is the actual watering hole frequented by “Papa.” The former morgue morphed into a cigar factory, ice house, and bordello before it became Sloppy Joe’s Bar in the 1930s. In 1968, Tony Tarracino, a local boat captain turned bar owner and then politician, ran the joint until he sold it in the 1980s (Sparacino died in 2008). Jimmy Buffett got his start playing at the bar, and Bob Dylan was a frequent customer. The bar, festooned with currency from around the world, is built around an old tree, said to be used for hangings. The bar also has as least two bodies buried (look for the markers) and, probably, countless ghosts, including, some say, Hemingway himself.
While Captain Tony’s is the original Sloppy Joe’s, this Duval Street bar is no slouch. The walls are decorated with all manner of Hemingway memorabilia, including pictures of past Hemingway lookalike contest winners. Stop in for live music by legitimately good bands almost any time of day or night and stay for a few Sloppy Ritas and a fish dip. If you’re into craft beer, Sloppy Joe’s has a craft beer bar around the corner on Greene Street that’s quiet and air-conditioned.
This three-story complex consists of three different bars: The Bull is on the first floor, offering an open-air (no airconditioning) old-school bar decorated with murals of the history of Key West. On the second floor, the Whistle has a balcony where you can grab a drink and overlook Duval Street. Venture up the stairs and you’ll be asked to put away your cell phones and cameras before entering the Garden of Eden. This “clothing optional” rooftop bar allows for sun (and moon) bathing everything (though you will never be pressured to take your clothes off). Drink, dance, and even take a peek — just don’t take any pictures. The vibe is actually super friendly, so feel free to be a little adventurous. I cannot confirm nor deny I spent my birthday dancing (in my birthday suit) with my boyfriend after a few too many.
The Hemingway family is very much involved in the making and distribution of Papa’s Pilar — a fine rum that’s offered in dark and blonde expressions. Tour the distillery or have a free tasting before entering a secret doorway that leads you to a Hemingway-themed bar that serves cocktails made with the rum made on premises. Opt for a Hemingway daiquiri (naturally), and don’t forget to toast Papa — in the form of a life-sized bronze statue.
The Green Parrot has been slinging drinks since 1890. The bar is a perfect place to seek shelter from Key West’s typical afternoon rain storms — just grab some free popcorn from the ever-popping machine, take a seat, and enjoy the live music that plays daily. The Green Parrot is also home to some of the best bloody marys you’ll ever have. The bloodys are made to order — ask for a checklist of items and the bartender will make you exactly what you want. This is a recommended early afternoon stop if you’ve had a really long night for obvious reasons.
Airplane buffs and historians will want to check out First Flight for its aviation-themed bar. The restaurant and brewery are located in the former Pan American Airways building, where passengers waited for their seaplanes to Miami and Havana. Formerly Kelly’s Caribbean Bar, named after past owner Kelly McGillis, First Flight offers excellent beers, including the Capt. Maverick IPA. First Flight is also a welcome respite from Key West’s typical dive bars — the space is so pretty, that many wedding ceremonies are performed here.
One of Key West’s places where you should sip your drink instead of downing it, the Rum Bar offers a selection of 350 different rums to choose from. This tiny bar is elegantly casual. It offers rum flights and classic rum-based cocktails.