Great drinks don’t always come from big bars. In fact, the smaller the venue, the better your chance of striking up a conversation with the bartender or the person next to you. Bay Area food writer and chef Illyanna Maisonet compares going to a small bar to seeing a band at a tiny club. “It’s way more intimate,” she says. “It's like your own little nook.”
One of New York City’s best bars is also one of its smallest. This place doesn’t even call itself a bar but a “bitters tasting room.” Every cocktail on the menu, as you would expect, boasts of its bitterness. While you will probably end up standing, you’ll undoubtedly enjoy your CIA, a creation by bartender Sother Teague containing Cynar, Punt e Mes and apple brandy.
They didn’t think too hard about the name of this one, the tiniest watering hole in Key West, Florida. At 72 square feet, its website boasts of it being “about the size of a jail cell.” Expect a heavy dose of tropical vibes, of course, and plenty of rum and juice drinks. And if home feels a little too far away, book a room in its guest house. (Don’t worry, the beds are of normal size.)
You have to reserve a stool here, because it’s only 157 square feet and the capacity maxes out at 12. Even the bartenders have to hop over the bar just to get behind the stick. The cash-only spot does have a photo booth, though, making it well worth stuffing yourself inside.
Trust the name of Chicago’s tiniest bar, which clocks in at a snug 460 square feet. You can also trust in the bartenders, who know their stuff and mix up pitch-perfect classic cocktails. The Matchbox has been operating for more than half a century, though its current incarnation has been going since 1995. Follow the locals, who pop in for after-work drinks, then get dinner at The Silver Palm, the next-door restaurant owned by the same folks.
Good luck trying to find this under-the-radar date spot. The entrance is through a small door off to the side of the Italian restaurant Aita, making it the perfect place to wait for a table before dinner. But the drinks are superb by their own right, despite the tiny backbar. You’ll likely find a locally made aperitivo or gin, and there are a couple nooks where guests are known the make out. So look before you creep.
M Bar has been open for almost 20 years, even though it’s not that easy to spot from the street. The banquette seating forces intimacy and doesn’t even allow for two-dozen people to sit comfortably, but the wine bar offers well-priced pours selected by owner and advanced somm Jeremy Campbell.