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An Insider Guide to Milan – The Iconic Fashion City Hosting the Winter Olympics

While we’re more accustomed to heading to Milan with fashion and design at the forefront, early 2026 is bringing something new to the city: the Winter Olympics. Come February, the northern Italian metropolis will share the limelight with Cortina for the 25th Winter Games, with the Paralympics following in March.

Milan will host ice sports, including figure skating and short track speed skating, at the Unipol Forum di Assago; speed skating at the Fiera Milano Rho Exhibition Center; and ice hockey at Rho Fiera and the new Arena Santa Giulia.

There will be official fan zones and public screenings across the city, but for those more accustomed to bouncing from one fashion party to the next, you may be a little, well, on your own. But fear not – we’ve tapped into the expertise of some of the individuals who know the city best, so that if you’re left to your own devices, or simply need a break from the crowds, you can enjoy Milan’s best local spots.

See more: The Must-See Moments From Milan Design Week 2025

For a quiet stroll in the city, head to the Navigli canals ©Shutterstock

The best restaurants in Milan to visit during the Winter Olympics

World-class pizza and pasta are, of course, aplenty in this Italian city, but be sure to make the most of Milan’s specialties and more traditional Northern Italian dishes, often found in low-key, relaxed trattorias.

In winter, Lombardians gravitate toward cassoeula, a braised veal shank cooked slowly until the meat yields to a fork, often served with gremolata. Risotto alla Milanese is also a must-try: a rich, buttery, golden-colored rice dish flavored with saffron. 

For something a little meatier, order cotoletta alla Milanese — a bone-in veal cutlet, pounded thin, breaded, and fried in butter. Crisp on the outside, tender inside, it is usually served simply, with no sides aside from a wedge of lemon.

Peck offers great food paired with fine wines ©Peck

“In Milan, my favorite place for lunch is Bacaro Montenapoleone,” says Fortela creative director Alessandro Squarzi. “It’s a hidden courtyard tucked away on Via Montenapoleone, with just a few tables. Their vitello tonnato is one of my absolute favorites, and they offer a well-curated wine selection.”

For traditional dishes, Ezio Indiani, general manager of the iconic Milanese hotel Savoia di Principe, recommends Trattoria Milanese. Or for something a little more contemporary, book into Ratanà – a beautiful old building in Isola.

The best bars in Milan

Milan’s drinking culture is built around routine, so if you want to blend into the background and not stand out as a tourist, you need to learn the rules. Days start with coffee (pastry optional) taken quickly and usually standing at the bar. For this, Indiani directs you to Caffè Cova, “a true Milanese institution.” A cappuccino is fair game in the morning, but ordering one after lunch will mark you as a visitor.

Caffè Cova is a true Milanese institution ©Shutterstock

In the early evening, the city shifts into aperitivo mode, Milan’s signature drinking ritual: a pre-dinner pause enjoyed with friends and unhurried conversation. Classic orders include a Negroni, Americano, or spritz, enjoyed with small plates that range from olives and crisps to more generous spreads, depending on where you go.

“For a good Americano cocktail, I always choose La Pesa Pubblica,” says Squarzi. “In the Liberty District, right next to the Fortela boutique, it’s a very low-profile spot with surprisingly well-crafted cocktails.”

Milan native Michele Lupi, of Italian shoe brand Tod’s, backs locals-only bar Norah Was Drunk, “a refined spot, even if not located in the center of town.” Named after the owner’s small dog, Norah, who would lick leftover glasses after dinner and end up a little tipsy, Lupi suggests ordering the Oyster Martini – a saltier take on the classic, served with an oyster inside. For side plates: “a plate of Pata Negra, an exquisite cheese assiette, and wonderful smoked salmon with sour cream.”

Villa Necchi Campiglio can be found in Milan’s Neighborhood of Silence ©Shutterstock

Then comes wine. Aperitivo hour can be enjoyed at one of the city’s historic wine bars – Indiani recommends N’Ombra de Vin for an intimate get-together – but for a true Milanese experience, let the evening be food-led. “Peck is ideal for a gourmet experience with fine wines,” he recommends.

See more: Heads or Tails? The Double-Sided Fashion Coin of Milan

The best things to do in Milan, aside from the Olympics

Beyond the Duomo, the Galleria, and the boutiques, Milan’s other landmarks often go overlooked. Indiani suggests a visit to Casa Museo Boschi di Stefano, “a small but stunning museum that combines modern art with Milanese history.” Make time for the Brera Botanical Garden, Via Lincoln in the Porta Venezia area, and Villa Necchi Campiglio, “a hidden architectural gem with beautiful gardens.”

“Among my favorite hidden gems is the Cimitero Monumentale, a place of silence and contemplative beauty, perfect for stepping away from the city’s rhythm,” says Valeriano Antonioli, CEO of Lungarno Collection and Portrait Hotels and Resorts.

Casa Museo Boschi di Stefano is a small modern art gallery ©Shutterstock

“More than a cemetery, it is an open-air museum and the final resting place of many notable Italians, including Gae Aulenti, the visionary architect whose passion for design has left a lasting mark on Milan. It is a powerful space where art, sculpture, and romanticism intertwine with reflection on life and death.”

There’s also Villa Necchi Campiglio, which Antonioli heralds as a “masterpiece.” Nestled in the city’s Neighborhood of Silence, the building was designed by Milanese architect Piero Portaluppi and offers a rare glimpse into Milanese high society of the 1930s, with elegant interiors and serene gardens.

To experience a true taste of Milan without the crowds of the Olympics, Indiani points you toward the Isola and Porta Nuova districts. “This is a vibrant area combining contemporary architecture, street art, and independent boutiques.” Other districts worth a visit include Porta Romana and Porta Vigentina, historic areas with charming streets, local cafes, and artisan shops.

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And for an early morning or late evening walk, stroll along the Navigli canals. “It offers the opportunity to see a quieter, more local side of the city,” says Indiani.

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