8 Of The Best Bars In Key West

Adam Gopnik, a critic and essayist for The New Yorker, wrote an article about the Florida crime novel entitled “In the Back of the Cabana.” Gopnik calls this regional caper genre the “fiction of Florida glare,” and it normally involves some combination of the following: amateur sleuths, bumbling newspapermen, eco-terrorists, shady real estate tycoons, petty criminals taking their cues from films like Scarface and Pulp Fiction, and ragtag smugglers hauling white lobster (cocaine) into the States from South America and the Caribbean. Key West, the southernmost point in the continental U.S., is a major player in the Florida crime novel. There's something about a far-flung outpost that’s closer to Cuba (94 miles) than Miami that attracts a certain type of character.

While the idea of fishermen moonlighting as drug smugglers went up in smoke in the ‘70s, those types of stories make first-rate crime novels, and Key West has more stories, legends, and tall-tales than most destinations. Nicknamed The Conch Republic, the 3,700-acre island has long been a haven for writers and artists. Ernest Hemingway made his home in Key West for over 10 years, and Tennessee Williams bought a Bahamian cottage in 1949 and listed Key West as his permanent residence until his death in 1983. Thomas McGuane, Jim Harrison, and Joyce Carol Oates all lived in Key West, and musician Jimmy Buffett, the patron saint of Duval St., has been “looking for his lost shaker of salt” for years in Key West. A number of movies have also been filmed on the island including “The Rose Tattoo,” “Operation Petticoat,” and “License to Kill.”

Being that every hour is happy hour on the island, bar hopping in Key West is not for the faint of heart. If Hemingway had too many longnecks at Sloppy Joe’s, he looked for the light of the Key West Lighthouse to guide him home -or so the story goes. Whether it’s true or not doesn’t matter. It’s good advice.

8 Hog’s Breath Saloon

Hog’s Breath is Better Than No Breath at All. That’s the motto of this 25-year old watering hole on the corner of Front and Duval Streets. The saloon features an outdoor tropical sitting area and an indoor, air-conditioned bar; the decor is best described as part biker chic, part Kenny Chesney concert. The raw bar is one of the best in the Keys, and the recipe for the Bahamian conch chowder is believed to been smuggled from the islands by the bar’s owner. From national and local bands to bikini contests and Leather and Lace parties, the Hog’s Breath Saloon features a range of live entertainment.

7 The Bull and Whistle

Located on the corner of Duval and Caroline, the Bull and Whistle is a large, three-tiered building that looks like it belongs on Bourbon St. in New Orleans.  An iron balcony wraps around the second-floor, giving the bar a French Quarter-meets-brothel type of feel. The first floor is called The Bull. It’s a large space with a small stage and a sports bar vibe. The second floor, known as The Whistle, is the darling of the party crowd, as the iron balcony provides a perfect view of the shenanigans taking place on Duval. Inside, the second floor has pool tables, darts, and old fashioned honky-tonk bric-a-brac. The third floor, however, is where things get interesting. Known as The Garden of Eden, the rooftop bar is clothing optional.

6 Willy T’s

Willy T’s mojitos are tastefully strong, but not overdone, with a healthy dose of fresh mint and sugar pestled to oblivion. Located on the quieter end of Duval Street, the open-air bar and restaurant attracts a diverse and easy-going crowd. Like pirates marking buried treasure, visitors pin dollar bills all over the walls of Willy T's; if a bill happens to fall (and they do, as money is plastered as thick as wallpaper), it’s donated to the Wounded Warriors Fund. Live music starts at noon, with local musicians playing oldies, country, and reggae until closing time.

5 Sloppy Joe’s

Key West has more bars per capita than any other place in the U.S., but no watering hole is as famous (or infamous) as Sloppy Joe’s. This was Hemingway’s beloved haunt, and the long curving bar, rickety ceiling fans, and jalousie doors that open onto Duval Street are the same today as when the American author was writing A Farewell to Arms. What has changed, however, is the amount of people that crowd into Sloppy Joe’s; from weekend warriors and literary tourists to cruise ship vacationers looking for “Papa” souvenirs at the bar’s store, Sloppy Joe’s is a hopping place, the floor often squishy with spilled beer and Cuban rum by 11 a.m. Hemingway famously called Key West “the St. Tropez of the poor,” but that is definitely not the description today.

4 Captain Tony’s

Ernest Hemingway, Truman Capote, Shel Silverstein, John F. Kennedy, and Harry Truman all drank at Captain Tony’s. In fact, when any celebrity visits a barstool is painted with the patron’s name. Located on 428 Greene Street, the building was originally built in 1852 and over the years it’s been an icehouse, morgue, wireless telegraph station, cigar factory, and bordello. And here’s where it gets confusing.

In 1930, the building was turned into Sloppy Joes Bar. It was Hemingway’s favorite watering hole during his time in Key West. However, after the landlord raised the rent, the entire bar then was moved to Sloppy Joe’s current location on Duval St. In 1958, 428 Green Street became the home of Captain Tony’s. Two other interesting facts: the tree inside the bar was Key West’s hanging tree in the 19th century; and legend has it if you put a quarter in the mouth of the large Jewfish that hangs above the bar's outdoor sign, you’ll have good luck on the island.

3 The Green Parrot

Billed as a sunny place for shady people, The Green Parrot is a Key West icon and continually rated as one of the Top Ten Bars in America. Once known as the Brown Derby Bar, it was initially a bunker-like hangout for sailors stationed at the Navy base in the 1950s and ‘60s. After the Navy left in the ‘70s, the bar became a haven for hippies, bikers, vagabonds and free-spirits, and the owner, Judy Sullivan, renamed it The Green Parrot.  The bar epitomizes the weird magic of Key West and draws a cross-section of locals from construction workers and fishermen to drag queens. The Green Parrot not only has an extensive and legendary jukebox, but Florida Monthly Magazine rated it the Best Live Music Venue in the state in 2010. Don’t expect to find food at The Green Parrot. As an article in Playboy magazine stated, “the management works tirelessly to avoid progress. Amen to that!”

2 Half Shell Raw Bar

Owned by former Philadelphia 76ers President Pat Croce, the Half Shell Raw Bar is a well-worn and much-loved waterfront establishment on Margaret Street. Inside the Half Shell there are license plates hanging on the walls from all corners of the world, a famous sailfish sculpture, an extensive row of draft beer taps, and table shuffleboard (even the bar games are quirky in Key West). Outside, picnic tables overlook the picturesque Key West Marina; patrons can watch the yachts and double-keeled catamarans come and go as well as the fishermen unhauling the day’s catch on the dock. The Half Shell Raw Bar doubles as a seafood market. Be sure to wash down that cold beer with conch fritters, conch ceviche, gulf oysters, or a bucket of clams.

1 Pepe’s Cafe

Tucked away in a small alcove on the old commercial waterfront of Caroline Street, Pepe’s Cafe was established in 1909 and is considered the oldest “eating house” in the Florida Keys. It’s quaint, funky, and laid-back; there are only 6 stools at the bar and a handful of tables on a flagstone patio fringed with bougainvillea and Spanish moss. Locals typically occupy the seats, or tourists who’ve been in Key West long enough to be in the know. Pepe’s serves breakfast, lunch, and dinner, and there are $1 oysters and $1.50 drafts from 4-6:30p.m. While Pepe’s isn’t located far from Duval Street or tourist-centric Mallory Square, walking into this bar is like stepping back in time.

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