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In a city known for fashion and elegance, you'd expect Milan's bar scene to be sophisticated – and sure, it's possible to sip aperitifs with the beautiful people in a vine-covered garden. But the city is also blessed with a surfeit of quirky watering holes, so if you know where to go, you can also knock back shots in a converted 18th-century church or play pinball in a bar designed by Wes Anderson.

Wes Anderson’s cinematic world

This bar's kitsch design and pastel colour palette draws you in like one of Wes Anderson’s whimsical movies – which is perhaps unsurprising since the cult film director is the brains behind ’s design. From the 50s formica tables to the Steve Zissou-themed pinball machine, the experience is like being immersed in Anderson’s cinematic world. Housed in the elegant Fondazione Prada, the bar also draws inspirations from the city itself; look carefully and you’ll notice details from Milan’s iconic Galleria Vittorio Emanuele II.

Country life in the inner city

You’ll forget you’re in the city at Cascina Cuccagna, a former 18th-century farmstead that has been beautifully repurposed as a cultural space, guesthouse, restaurant and bar known as Un Posto a Milano. While the kitchen emphasises locally sourced ingredients, some direct from their vegetable garden, the drinks menu includes sulphate-free Italian wine, craft beers and quality cocktails. It also hosts a weekly farmer’s market along with creative classes and events.

Cocktails by the pool

is a 1930s public swimming pool and theatre space that’s been painstakingly restored by Fondazione Pier Lombardo and is now one of the city’s most popular summer haunts. Not only does it make for a scenic dip, you can also sip cocktails poolside or sprawl on its lawns over an aperitivo. It has a full program of events, from tai chi classes to art shows, dance performances and electronic music concerts. In winter the swimming pool transforms into a magical place for ice skating.

Where drinking is sacrosanct

In a country famous for its many churches, it seems almost fitting to go for a casual drink in one. , a tiny 18th-century church in Milan's Chinatown neighbourhood, makes this possible. Its faded frescoes and gothic arches provide the atmospheric setting for cheap shots and themed cocktails (Sangue di Giuda aka ‘Blood of Judas’ anyone?) This boisterous locale gets busy so it’s best to get here early at the weekend if you want a seat.

The elegant winter garden

Sitting in is like being in an elegant winter greenhouse. Housed in the neoclassical Villa Reale, its large windows have original details from the 1700s, while its greenery includes everything from palm trees to cacti. The brainchild of three siblings passionate about the food from their home region, it goes without saying that the Sicilian-inspired menu is excellent. The Villa is also home to the Galleria d'Arte Moderna and a dreamy kids’ park, which provides yet another excuse to visit.

The smallest bar in the world

Imagine renting your own private bar for a couple of hours, where you can choose every detail, from the music to the glassware, while a masked mixologist whips up cocktails according to your tastes. Welcome to . Billed as the smallest bar in the world, at 4 sq m with space for only four people (including the barman), drinking here is an intimate experience. If that sounds too claustrophobic for you, you can get take-away cocktails outside, by ordering through a small window (only on weekends).

The Italian fashion concept

Fashion, art and design have no finer home than Corso Como 10, the famed concept store started by fashion magazine editor Carla Sozzani. And while various branches can be found in big cities around the world, there’s nothing quite like the original. Housed in a 20th-century palazzo, it offers high-end fashion, a design bookstore, gallery, a rooftop garden and a restaurant and bar. Its vine-covered courtyard is the place to sip cocktails with the well-heeled.

A Milanese institution

Step back into a time of 60s glamour at Bar Basso, with its chandeliers, velvet seats and waiters in white shirts and black ties. Famous not only for having served everyone from Frank Sinatra to a former President of the Republic, it’s a veritable Milanese institution for one very good reason. It was the first place to offer ‘aperitivo’ (a drink plus light meal) to the public and and the beloved Negroni Sbagliato cocktail was invented here. You can still enjoy this drink here in its original form: in a large goblet (known as the Colossus) with an enormous block of ice and a slice of orange.

The gin-lover's choice

It's all about gin at The Botanical Club, which not only has over 150 well-known and hard-to-find gins from all over the world, but also produces its own brand –Spleen et Idéal. It’s Italy's first small-batch distillery and a chic place to imbibe with its minimal aesthetic and lush overhanging greenery. It also serves up a mix of fancy modern dishes, such as vegetable tempura or Hawaiian Poke. Choose from two locations, the original bar in Via Pastrenga or the bigger and bolder one in Via Tortona.

Searching for the 1930s

There’s something irresistible about the speakeasy , and it’s not just the feeling that you’re in on one terrific secret. It’s also the inventive cocktails and classy vintage decor that takes you back to the time of American Prohibition. Hidden by what appears to be a Chinese convenience store, entry is only granted by invitation, which is notoriously hard to come by. If you don't know someone who's already a member, the best way to gain entry is by sweet talking the staff at Mag Bar (the parent bar of this locale), in particular owner and bar manager Flavio Angiolillo.