Key West, FL
Let’s get this out of the way up front—Hemingway drank here. For real. Indeed, Papa was a regular at this national treasure back when it was called Sloppy Joe’s Bar. It’s still pretty sloppy. Adorably so. Money and undergarments are tacked to the walls and ceiling. There’s a tree in the middle of the place from which pirates were purportedly hanged. It’s the kind of place where you’re definitely going to hear some Jimmy Buffett music, like “The Last Mango in Paris,” a track about a dude by the name of Anthony Tarracino, better known as Captain Tony. “It has all the atmosphere you'd expect of a quintessential dive bar,” says Bill York, founder of a craft bitters company. “And, you know, a hanging tree.”
Securing a reservation at the Michelin three-star restaurant French Laundry can be a challenge, to say the least, but not to worry: There’s always room for you down the street at Pancha’s. The food’s not as good, and neither are the drinks, the wine, the beer or the service. But, boy, is it ever a hell of a lot cheaper. And the ambience is a whole different kind of fun. “A word of warning though,” says Isaac Shumway, former beverage director at Tosca Cafe in San Francisco. “Do not piss off Rose the bartender.” She’s known for having a counterintuitive approach to bartender hospitality, one that’s roughly summed up by the framed sign in the bar reading, ‘Zero Tolerance for Idiots.’
“The Horse,” as it’s known roundabout Fell’s Point, was established in 1775. It’s purported to be the last place Edgar Allen Poe visited before his mysterious death on October 7th, 1849, and the locals say Poe’s ghost still haunts the place. “The Horse ticks all the boxes you love about a great old dive,” says Tobin Ellis, one of the country’s leading hospitality consultants. “Genuinely friendly bartenders, a ton of whiskey, a worn-in feel with horse saddle bar stools, and live music seven nights a week.” And this being Maryland and all, let it be noted that the crab cake is legit.