Scratch beneath the surface of Milan, the industrial-rich metropolis of northwest Italy, and you will find an idiosyncratic charm – one of elegant boutiques, old-fashioned pasticcerias, Renaissance art and atmospheric restaurants, all mixed in with the new and modern. Best of all, you can explore the city on foot

Bar Luce at the Fondazione Prada

Bar Luce at the Fondazione Prada

Welcome to Milan – perhaps Italy’s most elusively exciting major metropolis. Elusive? Why? Well, the old adage about this ancient capital of Lombardy is that the more you look, the more you see. Unlike, say, Rome, Venice or Florence, this is not a city that intoxicates you with its beauty upon first sight. It is a place of business, scarred by war, and inclined to discretion rather than display. Milan’s charms are perhaps less obvious – less blatant – than its rival capitals. But this makes them all the more satisfying to seek out and discover.

By far the best way to tackle Milan is on foot. The city has a one-way system so circuitously convoluted that a day spent touring it by car can leave the impression that this is a huge, sprawling place because of the time you will spend going from A to B via Z. It is, in fact, very compact.

Mandarin Oriental, Milan is situated in the heart of the Centro Storico – the city lies at your feet. In five minutes, you can be at the Teatro alla Scala (arguably the most beautiful opera house in the world), the Galleria Vittorio Emanuele II (arguably the most beautiful shopping mall in the world) and the Duomo (certainly one of the most intricate and awesome examples of devotional architecture in the world).

Even closer is Via Montenapoleone, Milan’s prime luxury fashion street, and as such one of the most important thoroughfares in the city. Here and on Via della Spiga, which runs adjacently, you have all of the chief boutiques of all of the fashion houses for which this city is so famed. The Valentino store, recently redesigned by David Chipperfield, is a must-browse, as is Versace, Prada, and multiple stores from Dolce & Gabbana (whose men’s boutique on Corso Venezia has a delightful barbiere). From Pucci to Gucci and Armani to Zegna, they are all here.

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Inside Villa Necchi Campiglio, a private house open to the public

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Nonostante Marras, a store from fashion designer Antonio Marras

The very first fashion boutique to open here was Larusmiani (Via Montenapoleone 7), which first moved in 61 years ago. It makes gorgeous, overtly luxurious, tailored mens- and womenswear and is an interestingly artisan option for shoppers in search of sleek, Milanese luxury attire. A short stroll to Corso Venezia takes you to De Padova, the first and among the most influential interior-design showrooms – whether you are in search of archetypal modernist classics or exciting innovations – in this furniture-obsessed metropolis.

There are also some great restaurants and coffee spots in this area. For a post-De Padova pick-me-up, Princi bakery, directly opposite, makes outrageously good pizza and pastries. For something more substantial, Bagutta – named after the side street it resides on – is an institution. Decorated by generations of Milan’s finest artists, the atmosphere in this delightful trattoria is relaxed (although the waiters can, on occasion, succumb to brusqueness) and the food reliably excellent.

The old adage about this ancient capital is the more you look, the more you see

A touch more formal and old-fashioned is A Santa Lucia (founded in 1929) on nearby Via S Pietro All’Orto. Famous diners to have adorned its tables include Josephine Baker, Liza Minelli, Plácido Domingo and Alain Delon. After savouring its robustly traditional pasta or pizza, you may need a constitutional stroll – so either wander the forests of fashion again, or walk five minutes to Giardini Pubblici Indro Montanelli, one of Milan’s largest and most intricately landscaped parks. Another option is the extraordinary Villa Necchi Campiglio, on Via Mozart. But before you set out, do ask your concierge to confirm it is open to visitors. This glorious Thirties private house, designed by Piero Portaluppi for the scions of a sewing machine fortune, is popular with filmmakers and fashion houses and so is sometimes closed even during its supposedly open days (Wednesday to Sunday). There is a small entry fee, unless you wish only to sit in the glorious garden. But it is well worth seeing the interior of this beautiful, slightly melancholy, minor architectural masterpiece.

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The Galleria Vittorio Emanuele II shopping mall

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Pupi Solari, famed in Milan for her eponymous boutiques

Another neighbourhood only a short walk from Mandarin Oriental is Brera, a quartiere that drips with history and is blessed with plenty of pedestrianised areas bristling with quirky boutiques, bars and restaurants. There are fewer big-name international brands here, which means you are more likely to find something particular to Milan. A chief example of this is the store, on Via Brera, of Massimo Alba. His high-quality clothes for men and women have a light touch but distinctly handcrafted feel, and like the man himself are never – all right, rarely – loud.

A few doors along is Cavalli E Nastri, which demonstrates perfectly the value of buying well-made items: treated respectfully, they will not only last for years but might even have a second life. The Milanese consume high fashion almost as enthusiastically as they produce it. So this, one of the city’s prime vintage boutiques, tends to be heaving with wonderful pre-worn classics.

For older examples of Italian artistry, still on Via Brera, head for the imposing façade of Pinacoteca di Brera. This grand but lived-in neoclassical palazzo is Milan’s main depository of Old Masters and boasts a punchy collection of Renaissance art, with works by Bellini, Bramante, Raphael, Tintoretto and Caravaggio filling its galleries. Unusually for a site of such importance, the building is quite rough around the edges (graffiti artists are well represented here, too!), but this adds to its charm, as does its quietly lovely garden.

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Luxury Milanese fashion retailer Larusmiani

Close by, on Via Montebello, is another satisfying Brera institution, with a sideline in flora: Fioraio Bianchi Caffè. This is a beautiful dining experience, thanks not only to the sophisticated lunch and evening menus but also the flowers. They are everywhere, fresh every day, creatively arranged, filling the room with aroma – and all for sale.

Also highly recommended is La Latteria on Via San Marco – but here it pays to eat early in the evening. La Latteria has fewer than 10 tables, doesn’t take bookings, and is a favourite haunt of Corriere della Sera journalists, whose offices are nearby. However, if you turn up early (around 7.30pm), you might reap the benefit of this kitchen’s beautifully executed take on local classics.

Speaking of classic, no student of Milan should fail to visit Corso Magenta – a short cab ride from Mandarin Oriental – and its surrounding streets. This area represents quintessentially old-fashioned Milan: bourgeois, mannered, conservative – but fun, too. Before exploring it, though, have a coffee at Pasticceria Marchesi on the corner of Via Santa Maria alla Porta and Corso Magenta itself. Milan heaves with pasticcerias – unassuming, often attractively appointed, local coffee and cake shops. Marchesi is one of the oldest in town (it opened in 1824), and a mesmerising spot in which to inhale an espresso and enjoy the almost theatrically baleful demeanour of its seen-it-all staff. Well-dressed locals gossip at the bar and take fastidious bites of delicious pastries. So beloved is Marchesi in Milan that Prada recently spent several million euros on securing a majority stake. With typical sensitivity, they have since left it entirely untouched.

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The marble-covered Mandarin Bar

Walk on, 20 metres or so, and duck into Lorenzi on Corso Magenta. This marvellously higgledy-piggledy store is a masculine apothecary, whose gleaming cabinets heave with niche colognes and luxurious shaving paraphernalia. Lorenzi also stocks a mean selection of chef’s knives. Another authentic if not the Milanese experience can be had if you enter Piazza Tommaseo 2 in Google Maps and let it lead you to Pupi Solari. This redoubtable retailer has (impeccably) dressed generations of locals in her surgically tasteful selection of clothes since 1969.

The greatest attraction in the Corso Magenta area – if not in all of Milan – is The Last Supper, in the church of Santa Maria delle Grazie. But viewing Da Vinci’s masterpiece mural is not something you can do on a whim: well before your Milan visit, book a tour or appointment that will give you a golden ticket to stand in front of this gloriously immersive mise en scène. A bucket list experience if ever there was one.

Afterwards, you will need a breather to digest the memory of what your eyes have feasted upon. Try Bar Magenta on Via Carducci: this wood-panelled corner bar has been operating for decades and has a pleasing aura of genteel abandon. Not the place to order anything too niche, but absolutely the spot for an Aperol Spritz or a birra alla spina and a moment imbibing a properly Milanese atmosphere. It gets busy, and quite young, late at night and on weekends.

Santa Maria delle Grazie, home of Da Vinci's 'The Last Supper'

Santa Maria delle Grazie, home of Da Vinci's 'The Last Supper'

Across the train tracks at Porta Genova (take the locally famous green iron footbridge) is Zona Tortona, a sort of Silicon Valley for fashion that houses the headquarters of companies including Ermenegildo Zegna, Moncler, Armani and Fendi. This is where many of the catwalk shows during Milan Fashion Week happen, and is also the locale of Nonostante Marras, a beautiful jumble of furniture, books, interior design, and – vitally – clothes, housed inside a weathered former warehouse and masterminded by the fashion designer Antonio Marras.

For a party atmosphere, however, immerse yourself in the Navigli. On the southern side of Milan, about a 20-minute cab ride from the hotel (traffic depending), this is a unique corner of the city thanks to the canals that cut through it. The streets alongside them are lined with restaurants and bars, and it’s a popular place to gather in the evening from aperitivo o’clock right through to the small hours. But before diving in, try reputedly one of Milan’s most pleasurable beauty experiences. On Viale Col di Lana, Bahama Mama is a nail-bar vintage-store hybrid that gets consistently rave reviews. And who can argue with combining a manicure with the acquisition – if you’re lucky – of some vintage Moschino?

Concept store 10 Corso Como

Concept store 10 Corso Como

Afterwards, both spruced up and dressed up, you’ll be perfectly poised for a passeggiata – with plenty of stops along the way. One of them could be at Spritz Navigli, on Ripa di Porta Ticinese. This is a pretty typical, but extremely well-sited, place to enjoy your aperitivo. For a fixed price, you get one drink plus free rein at a buffet piled high with bruschetta, salads, pizza and antipasti. For more meaningful sustenance, Al Pont de Ferr, also on Ripa di Porta Ticinese, looks like a traditional osteria but is anything but: this Michelin-starred restaurant specialises in creative gastronomy yet eschews fussiness, pomposity and hyper-inflated prices, and is well worth booking as the heart of a night spent in the Navigli.

On the same stretch of canal, MAG Cafè is a great next stop. The drinks menu is long, the mixology expert, and the atmosphere buzzy but not raucous. Alternatively, end your day with a cocktail in the sophisticated black and white marble Mandarin Bar & Bistrot at Mandarin Oriental, Milan, or in its ambiently lit courtyard.

Milan is as densely packed with delights as a good ossobuco is with flavour

After a late night, a soothing re-entry into daytime might be required. Wearing sunglasses indoors certainly won’t be frowned upon at the new Milan headquarters of Fondazione Prada on Largo Isarco. Those who have visited it rhapsodise about the harmony of its architecture, its gold-leafed tower, and the incredible display of art from the Fondazione collection. Perhaps the biggest buzz, however, surrounds the retro Milanese café designed by film director Wes Anderson.

Another fine venue for effortless atmosphere is 10 Corso Como, a short walk north of Brera down Corso Garibaldi – home of Rossignoli, Milan’s best bike shop. Corso Como has made the street it is named after internationally famous thanks to Carla Sozzani – sister of Italian Vogue editor-in-chief, Franca – who opened an art and design gallery here in 1990. Then came the café, the bookshop, and the store. Reputedly the site for which the first use of the phrase ‘concept store’ was coined, this is a warren of a venue to explore and enjoy.

Fine dining in the courtyard of Seta at Mandarin Oriental, Mila

Fine dining in the courtyard of Seta at Mandarin Oriental, Milan

On close-by Piazza XXV Aprile, in a former concert hall once graced by Billie Holiday, lies Eataly, the final stop of this hither and thither Milanese ramble. Milan’s outpost of this wonderful chain of food halls is marvellous. As well as cafés and restaurants aplenty, shelf after shelf is stacked with regional specialities including hundreds of pasta sauces, which make perfect presents to take home. There is also a wide collection of cooking utensils and recipe books, in case all that exposure to Milanese cuisine has fired a desire to make it yourself.

Milan is as densely packed with delights as a good ossobuco is with flavour, and this is, by no means, an exhaustive guide to them. As you wander you will find favourites of your own. Because the more you look, the more you see.

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