Compared with knockout Italian cities like Florence and Venice, Milan–considered the “handsome” sister–is gray and polluted and chock-full of Fascist architecture. But, as happens with siblings, the one without the looks usually has the most personality and style. Just as a perfectly tailored designer dress can change the woman who wears it, Milan’s star couturiers and luxury boutiques have transformed the city into Italy’s chicest, most modern metropolis, and one brimming with attitude and sophistication.

Cheat Sheet

  • Sleep…at the family-friendly Four Seasons Milano
  • Experience…a private viewing of The Last Supper with a plugged-in tour guide
  • Splurge…on a stylish suite at the Armani, the city’s ultimate design hotel
  • Eat…lunch or dinner at the old-fashioned yet fashionable Da Giacomo
  • Drink…espresso at Fioraio Bianchi Caffè in the bohemian neighborhood of Brera
  • Savor…the atmosphere at Gold, a café owned by Dolce & Gabbana
  • Visit…the Pinacoteca di Brera to see works by Raphael and della Francesca
  • See…an opera or the ballet at the fabled La Scala
  • Shop…at 10 Corso Como, terrific lifestyle boutique
  • Know…that as an Indagare member you can contact our Bookings Team for customized recommendations, special access and itineraries.

Read Indagare’s Top Tables Milan.

Lay of the Land

“What a wonder it [the Duomo] is! So grand, so solemn, so vast! And yet so delicate, so airy, so graceful! A very world of solid weight, and yet it seems...a delusion of frostwork that might vanish with a breath!”
~Mark Twain

Milan’s beating heart is the fashion district, Il Quadrilatero d’Oro, which is defined by four major thoroughfares: Via Montenapoleone, Via Manzoni, Via della Spiga and Corso Venezia and include Via Borgospesso, Via Santo Spirito, Via Sant’ Andrea and Via Gesu.’ Here you’ll find the glittering flagships of Italy’s premier designers: Gucci, Ferragamo, Missoni, Ferretti, Prada, Coveri, Cavalli, Versace, Trussardi, Dolce & Gabbana, Krizia, Moschino, Marni, Laura Bagiotti, Bottega Veneta, Ferragamo, Ferre, and Valentino. Of course most international high fashion brands are also present like Kenzo, YSL, Louis Vuitton and Chanel.

The historic center of Milan is a diamond in the rough. While some areas of the buzzing city are overlooked, the Centro Storico is beautifully maintained and has an easy air of class and glamour to it. Here resides the Duomo and some excellent shopping. Brera, a district within walking distance just north of the historical center, revolves around the street of the same name, and is home to the city’s finest art galleries, jewelry stores and unique antique shops and clothing stores. Akin to Paris’ Montmarte neighborhood, Brera has a friendly creative atmosphere, which becomes especially lively at night. Via Solferino is another important shopping street in Brera with a high-end outdoor market in San Marco Square twice a week.

The neighborhood of via Tortona comes alive in April during the Milan’s Design Fair (il Salone Internazionale del Mobile di Milano), which is arguably the world’s most important design fair (it attracts even more people than Milan’s glamorous fall and spring fashion shows). Over the last few years, it has started to draw more than just the trade but a wealthy, design-savvy crowd with lots of outsider events and happenings at galleries and shops in this area, which is far from the actual trade fair in Rho on the outskirts of Milan.

And with design taking a front-row seat next to fashion, it should come as no surprise that Milan itself is undergoing a makeover. The center of the city has expanded to welcome two new developments: Porta Nuova and CityLife. The former is a residential and commercial area designed by Zaha Hadid, Daniel Libeskind and Arata Isozaki. The complex has skyscrapers of offices and apartments as well as shops and a big green park. The Porta Nuova is the other new neighborhood just beyond the popular Garibaldi Corso Como neighborhood. Porta Nuova was designed by famed Argentine architect Cesar Pelli and incorporates state-of-the-art sustainability technology. There are two “vertical forest” skyscrapers, a hotel, shops, apartments, parks, commercial spaces, an exhibition center for fashion shows and a fashion museum. Its central square is dedicated to Gae Aulenti, one of Italy’s most famous architects and interior designers.

Way off the beaten path is the Corso Vercelli neighborhood where well-to-do families live. It’s a clean and bustling residential area with local restaurants, bars and independent shops. There are not as many hotels in this area but it’s worth checking out to come in contact with the local classy style of its residents.

When To Go

The only time Milan slows down is during the month of August when Italians take their annual vacations and the city is a ghost town. An ideal time to visit is the first two weeks of December when the holiday season in Milan begins with the annual feast day of St. Ambroeus on December 7th. The city empties out, which makes it a nice time for Americans to go for two reasons—great holiday shopping and good hotel rates. Avoid July and August: the summer months are hot and humid, and in August many shops are shuttered.

The most exciting time to be in Milan is during the International Furniture Fair in April. Hotel rooms go quickly, so plan your trip at least four to six months in advance. The neighborhood of via Tortona, which hosts the annual fair, becomes an amazing showcase of modern design, with galleries and exhibitions popping up in almost every courtyard and storefront.

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Beyond… Milan

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