One of Italy’s most dynamic cities, Milan is a hub of design, fashion, art, and business that delivers classic (and delicious) Italian culture with a modern flair. As the capital of the Lombardy region, it’s a financial powerhouse that’s heavily invested in urban renewal, green renovation, and technological innovation. But thanks to its location—one hour from Lake Garda and Lake Como in the Alps, and two hours from the beautiful Mediterranean Sea—it’s also one of the most attractive destinations for international tourists looking to explore the outdoors.

 

And if you want to experience its distinct blend of tradition and innovation, now is the perfect time: During the colder months, Milan is the perfect starting point for exploring the snowy peaks of the Alps (the Dolomites to the east are also a deluxe destination for winter holidays), while the Valtellina region is a prime spot for sports and wellness lovers who seek out signature gastronomic experiences. In addition to its proximity to the slopes, Milan features a myriad of art and design exhibitions, nightlife and fine dining experiences, and luxury shopping.

 

Not sure where to venture first? We asked locals about their favorite neighborhoods for a dreamy winter vacation in Milan. Here are some of the ones in this dynamic city—now just one year out from hosting the Winter Olympic Games in 2026—that came up most often.

Downtown Milano: Art, Fashion, and Opera

Piazza Duomo—where the Milan Cathedral proudly stands—is where this city reveals its soul. At the end of the fabled iron-and-glass Galleria Vittorio Emanuele II, a triumph of Italian Belle Epoque architecture with its refined stores and cafés, you’ll find Teatro alla Scala in all its Neoclassical splendor. Dating back to 1778, La Scala is one of the oldest and most important opera theaters in the world, and a key piece of Milanese culture.

 

Continue past the cathedral to the visually striking Museo del Novecento, with its modern-art exhibits and Futurist masterpieces. Pinacoteca di Brera is the national art gallery, offering Renaissance paintings by Raffaello Santi and Andrea Mantegna as well as the Romantic paintings of Francesco Hayez. And this past December 7—coinciding with Sant’ Ambrogio, the celebration day of Milan’s patron saint—the modern-art museum Palazzo Citterio opened the extraordinary exhibition “Greater Brera,” which encompasses masterpieces by Modigliani, Boccioni, Carrà, and Morandi, as well as the Vitali Collection and Pellizza da Volpedo’s La Fiumana.

Porta Venezia: A Welcoming Neighborhood

Porta Venezia, a multiethnic and hospitable enclave close to the city center, is marked by the rococo gardens of Via Palestro. New restaurants and bars pop up here every week, and it also serves as Milan’s rainbow district. For art lovers, Casa Galimberti, with its floral motifs and painted tiles portraying scenes of sensuous merriness, is one of the best examples of Liberty-style architecture in all of Europe.

Porta Romana: Amazing Gastronomy and Olympic Vistas

A melange of college students and urban professionals featuring restaurants and theaters in a turn-of-the-century setting, Porta Romana offers a nearly endless variety of Italian regional and ethnic cuisines and traditions. A tour to Fondazione Prada, one of the world’s best contemporary-art and film centers, is the perfect way to explore the neighborhood’s diversity. And come next year, skiers, skaters, snowboarders, and hockey players competing in the Winter Games will live here during Milano-Cortina 2026. The development of this vast park will create a whole new district, and an exciting new chapter for Milan.