The Southernmost City is known for its watering holes. Over the years, some have taken on legendary status because of their famous clientele. (Ernest Hemingway seems to have been a patron pretty much everywhere in Key West.) Others have entered into the pantheon of greatness due to their location or lack of adherence to any particular dress code…mainly nudity. One is a Key West original named after a famous song about a margarita that’s grown into a national empire. It seems you can get a drink on almost every corner in Key West, which is a good thing since partaking in alcoholic libations is one of the biggest reasons people visit. So if you’re headed all the way down to Mile Marker 0, here are our suggestions for the coolest places to grab a drink in Key West.
Sloppy Joe’s Bar – We might as well start off with the most storied dive bar in the nation – Sloppy Joe’s. This open-air bar at the corner of Duval and Greene Streets is the epicenter of the annual summer celebration that pays tribute to 20th century novelist Ernest Hemingway. For a week in late July, stocky white-bearded men who bear a resemblance to Papa descend on the bar for a look-a-like contest. The rest of the year, Sloppy Joe’s is the place to be and be seen while listening to local and national music acts.
Captain Tony’s Saloon – This colorful bar a few doors down from Sloppy Joe’s at 428 Greene Street is the place Hemingway himself frequented when he lived in Key West. Barstools at Captain Tony’s have seen the likes of Harry Truman, Jimmy Buffett, Truman Capote and John F. Kennedy. The building itself is Key West through and through. In its early days, the structure served as a morgue and later as a telegraph office. Today, in addition to being known as the “original Sloppy Joe’s,” Captain Tony’s is famous for its unique interior; vintage license plates cover the walls, countless women’s bras hang from the ceiling, and a large tree with an egregious past grows inside the bar.
Jimmy Buffett’s Margaritaville Cafe – Yes, you can find one of Jimmy Buffett’s tropical-themed restaurants in almost every tourist town in the country. But this location smack-dab in the middle of Duval Street is the one that started it all. So if you’re a die-hard Parrothead, someone who’s searching for his lost shaker of salt, or just need a frozen concoction to help you hang on, this place is a must.
Turtle Kraals – Located in the Key West Bight Marina, Turtle Kraals has been a popular spot with locals and tourists since 1980. Imagine sipping on your favorite cocktail while watching an old schooner departing the historic seaport for a sunset cruise or an adventure-seeker parasailing over the turquoise waters. You can see it all from the second-floor deck known as the Tower Bar. Still not convinced? Need more entertainment? Three nights a week, the restaurant hosts the Bahamian pastime of turtle racing where patrons “whoop and holler as four box turtles scurry from start to finish”
Green Parrot Bar – Diagonally across the street from the Monroe County Courthouse, the Green Parrot Bar has seen a lot of action since it came into existence way back in 1890. Cuban and Bahamian transplants used to take part in late-night impromptu jam sessions here and submarine sailors stationed at the Navy base a block away frequented the bar when it was known as The Brown Derby. The name was changed in the 1970s to the Green Parrot and the open-air bar has been a place to meet eccentric characters ever since.
Hog’s Breath Saloon – “Hog’s breath is better than no breath at all.” That’s the motto at this popular Key West watering hole and you probably won’t be able to leave town without purchasing a t-shirt or coffee mug emblazoned with the famous logo. A staple on the island since 1988, Hog’s Breath is a big hit with tourists “looking to blend in with a Key West flair.” The raw bar features local seafood, and the grill’s menu has something for every taste from pulled pork sandwiches and burgers to chicken wraps and tacos.
The Bull & Whistle Bar – The large stately building at the corner of Duval and Caroline Streets actually houses three distinct drinking venues. The Bull on the ground floor is the oldest open-air bar in Old Town Key West, while The Whistle a floor above provides a bird’s eye view of the crazy happenings on Duval. But the most talked about establishment at this location is a rooftop bar called the Garden of Eden. The fact there’s no air conditioning here really isn’t a problem. Just shed the clothes and join the fun!