The Best Places in Italy

Wine labels plaster the ceiling at this old-school Venetian wine bar tucked into a narrow alley near the Rialto, and the cellar below holds over a thousand bottles at prices that feel slightly illegal for Venice. Rough wooden benches, bare planks on the walls, and a glass counter piled with cicheti complete the picture. Locals have been doing exactly this, a glass and a small bite, here for generations.

A handful of bar stools at a grey marble counter, and the rest of the room is tightly packed tables that belong to diners at mealtimes. Harry's is a cocktail bar that trades heavily on its history, and it earned every bit of it: this is where the Bellini was invented, and Hemingway was a regular. It's small, plain, and slightly intimidating to walk into, which somehow makes ordering one feel like an occasion.

A 15-meter bar counter lined with bamboo shelves stacked floor-to-ceiling with rum pretty much tells you everything. Rita's Tiki Room is a cocktail bar on Milan's canalside strip, serving Tiki classics and house originals alongside Polynesian snacks with a Cantonese edge. The same team behind Rita around the corner runs this one, and the vibe is full commitment: proper accoutrements, no ironic winking at the theme.

The sign is easy to miss, which seems to be part of the point. This cocktail bar in Porta Romana pulls you into a low-lit room of velvet sofas, extravagant mirrors, and sparkling lights that make it feel like the '80s never quite ended. The kind of place where you stop checking your phone without deciding to. A neighborhood worth wandering for its trattorias anyway, so the detour is painless.

A corner bacaro a short walk from San Marco, with shutters thrown open and barely a meter of corridor to stand in. The reason to know it is the hours: open until 1am most nights and 2am on Saturdays, long after Venice has gone to bed. Drinkers overflow onto the campo, voices carrying loudly enough to navigate by, which the neighbors have noted and the police occasionally confirm.

The Negroni Sbagliato was born here when the owner grabbed sparkling wine instead of gin and decided to serve it anyway. Bar Basso is an old-school neighborhood cocktail bar in Milan that has barely changed since the late fifties, and the happy accident has been the house drink ever since. Order yours in one of the enormous chalice glasses the original owner designed, a shape you'll start spotting around the city once you know to look.

Surfboards and antique furniture share wall space at this cocktail bar on the far edge of Milan, and somehow the combination works. The room feels less like a city bar and more like a countryside detour, all mismatched art and skating decks, with a plant enthusiast behind the counter shaking what Italians have always called "misture." Five kilometers from the center, which is exactly far enough to feel like you've escaped something.

A windowless room on Via del Moro in Trastevere, done up in dark wood and overhead luggage racks like a very stationary Orient Express car. Jerry Thomas is a classic cocktail bar with 90-minute reservations and bartenders dressed for a century ago, which suits the bottled classics and Champagne on offer. Outside, Trastevere does its rowdy thing; inside, you'd never know.