Don’t pigeonhole Milan. Italy’s fashion capital is far more than incredible clothing and snazzy shoes. Milan is Bel Paese’s (“beautiful country” in Italian) most contemporary city, with a history of innovation that weaves through the centuries. It’s time to invest in a long weekend and we’ve got the itinerary to fill three perfect days in Milan.
Check into Four Seasons Hotel Milano for a fully immersive Milanese experience. Set in a former 15th-century convent, the Forbes Travel Guide Four-Star hotel occupies an enviable location on Via Gesu in the historic Brera neighborhood. The posh perch puts you in the heart of the city’s fashion district, where neighbors include a mix of designer boutiques (Armani, Prada, Fendi) and local artisanal shops.
You’ll want the keys to the Fashion Suite (Suite 444), a 730-square-foot pied-à-terre outfitted with Fortuny fabrics, Frette linens, custom-loomed carpets and a nearly 300-square-foot terrace.
To get a feel for the city, start with a curated walk with Context Travel. Our pick is a customized architectural tour led by a local guide that highlights the evolution of modern Milan though the city’s most important buildings. While you’re enjoying the architecture, make sure to peek into only-in-Brera boutiques like Cavalli e Nastri, a warren of vintage haute couture finds.
End your walk at Pinacoteca di Brera, an impressive Renaissance gallery and home of the 250-plus-year-old Accademia di Belle Arti di Brera art school.
After a jaunt through the city, you deserve an aperitivo. Indulge in this Italian tradition in the garden of Bulgari Hotel Milan’s sundrenched Il Bar. This Four-Star boutique hotel has all but perfected happy hour with a non-stop assortment of delectable snacks to accompany your negroni.
Keep the artsy vibe going with dinner reservations at Voce Aimo e Nadia in the gorgeous Galleria d’Italia. The design is Milan chic: simple, stylish and understated luxe, like the cleverly curated menus by superstar chef duo Fabio Pisani and Alessandro Negrini. Look out for changing tasting menus designed to complement the adjacent gallery’s rotating displays. “L’Ottocento” celebrates the “The Italian Nineteenth Century” exhibition through five period-inspired dishes. After perusing the paintings, savor plates like Milan’s iconic saffron risotto, “milk and honey” herb-crusted chicken breast with dried figs and eggplant, and a limoncello-infused babà cake.
Catch up on the city’s stylish history at Triennale Milano, Milan’s museum dedicated to all things design that’s less than 10 minutes from your hotel room. Lose a few hours studying pieces by notable names like Paola Antonelli, Mario Bellini, Piero Lissoni and Patricia Urquiola in the newly opened Museo del Design Italiano permanent exhibit.
When you’ve had your fill of design details, head up to the gallery’s rooftop restaurant Terrazza Triennale for a whole new perspective on the city. Soak up the pleasant breezes that flow through the open-air dining room while you nosh on chef Stefano Cerveni’s classics, like cacio e pepe (Italy’s peppery version of mac and cheese), costoletta di vitello alla milanese (traditional Milanese veal chop), asparagus soup with poached egg and crispy Parmesan cheese, and a variety of salads.
After lunch, double-back to the Four Seasons for some well-deserved relaxation at the subterranean Four-Star spa. Partake in a bit of rejuvenation with the restorative Gold Fashion in Milan treatment, before swimming a few laps in the 46-foot pool beneath the beautiful brick-vaulted ceiling.
Refreshed and ready, head out to explore modern Milan at Fondazione Prada, a sprawling, 200,000-square-foot complex dedicated to contemporary art. Entertain your senses with exhibitions overflowing throughout the massive facility, including a nine-story tower, an open-air cinema and Bar Luce, a cocktail and snack bar designed by Wes Anderson with subtle hints to all of the director’s films — like The Life Aquatic pinball machine, for example.
Scale the Rem Koolhaas-designed tower to get eye to eye with larger-than-life sculptures by Jeff Koons, Damien Hirst and Carsten Höller, and plan to stay for dinner at Torre, the sixth- and seventh-floor bar and restaurant that shows off the 21st-century Milanese landscape.
If you prefer something more low-key and local, book a table at Nebbia. Part of a new generation of trattorias, the minimalist space serves up a menu of innovative takes on regional recipes. Must-try dishes include roasted pumpkin with goat milk and sesame, chicken wings with Sichuan pepper and bok choy, duck pâté with Tropea onions, and a mind-blowing semifreddo (semi-frozen gelato-like) dessert. And if you can, get an invite to 1930, an after-hours speakeasy whose address is given only by request via the bar’s social media channels.
Rise and shine with a morning stroll on Via Montenapoleone, one of Europe’s most expensive shopping streets. Slide up to the counter at Pasticceria Cova for a quick cappuccino and freshly baked pastry beneath sparkling chandeliers before heading on to Via Spiga for a look into Nilufar Gallery, the exhibition space of Nina Yashar, one of Milan’s top design dealers.
With the arts and angles still on your mind, make your way to the Maroncelli District, the city’s latest enclave of boutiques, galleries and studios.
If you’re hungry, just around the corner is 10 Corso Como, a fashion concept store and café, and AMOR, the latest outpost from culinary stars (and brothers) Massimiliano and Raffaele Alajmo, whose patented steamed pizza turns the tables on the traditional pie.
End the weekend at one of the city’s most iconic sights: Piazza del Duomo. The unforgettable gothic cathedral is centerpiece to a neighborhood of architectural landmarks — and shopping. One of Italy’s oldest continuously used malls, Galleria Vittorio Emanuele II is great for photo opportunities and fabulous boutiques. Stop into department store La Rinascente to check out the latest vintage-inspired collection from American designer JJ Martin’s popular La Double J label. Once you’ve finished shopping, climb to the top of Duomo di Milano to stand among its 3,400 statues, 135 gargoyles and hundred-some spires watching over the city. If the 250-step climb (or elevator ride) is too much, just enjoy the view, and reflect on your time in Milan, with a spritz on the Terrazza Aperol.