Gothic cathedrals, art deco villas, vintage yellow trams, impeccably dressed signore, bright red Negronis glinting in the sun—these are some of the most classic symbols of Milan, but there’s a whole other side to the city, one that’s contemporary, cosmopolitan, and just plain cool. As Italy’s economic powerhouse—and fashion and design capital—Milan draws entrepreneurs and creatives from all over Italy and beyond. Now the northern Italian city is preparing for a major moment in the spotlight as it gears up to host the 2026 Winter Olympics together with Cortina and the Dolomites. As a Rome-based journalist, I love Milan for its bold energy and the way it simultaneously clings to its traditions. I’ve gotten to know the city well through repeat visits and designed this four-day itinerary, with help from a few plugged-in locals, for the ideal long weekend in Milan.
Thursday: Classic sights and bites
Don’t miss the views from the rooftop of the Duomo as well as from the piazza.
Photos by Michelle Heimerman
Any trip to Milan should start in the city’s geographic and spiritual heart: the Duomo. A symbol of the city, the enormous Gothic cathedral (the second largest church in Italy after St. Peter’s Basilica in Rome) took 600 years to complete and was finished in 1965. Join the crowds taking photos of the ornate building from the piazza, and then ascend to the terrace to marvel at the 135 gargoyles and other carvings up close and take in the city’s skyline. (Tickets for access to the terrace can—and probably should—be bought online in advance to ensure availability; the cost ranges from 16 to 36 euros.)
Afterwards, walk through the dazzling Galleria Vittorio Emanuele II, pausing to admire the glass dome and beautiful mosaic floors (but beware of pickpockets). Legend has it that spinning three times with your right heel on the testicles of the bull in its center will bring you good luck. Inside the gorgeous Belle Époque shopping mall, you’ll find designer stores as well as a few upscale restaurants and bars. For a nearby breakfast about a 12-minute walk away at a classic Milanese pasticceria, Neri and Akriti Baccheschi Berti, the husband-and-wife couple behind the boutique hotel Vico Milano, suggest going to the original location of Marchesi 1824 on Via Santa Maria alla Porta (now a small chain of three locations owned by Prada) for a cappuccino and brioche (that’s what they call croissants here).
For shopping in a gorgeous Belle Époque mall, head to Galleria Vittorio and then treat yourself with cake and pastries at Marchesi 1824.
Photos by Michelle Heimerman
Walk 15 minutes northeast to Brera, one of Milan’s most picturesque neighborhoods, full of narrow streets lined with stately buildings. Make a beeline for the Pinacoteca di Brera, the venerable art museum containing paintings by masters like Raphael and Caravaggio. The museum displays pieces from the Middle Ages through the 19th century. To see 20th-century works by the likes of Picasso and Modigliani, walk three minutes to Palazzo Citterio, which is part of the Grande Brera museum and library network.
Antonio Amorena, head travel designer and sales manager for the Milan office of luxury travel company Imago Artis Travel calls Brera his favorite neighborhood. “It’s a haven for fashion lovers looking for unique pieces, artisan jewelry, and emerging designer labels you won’t find elsewhere,” he explains. On my most recent visit, I bought a pair of bright green suede sandals at Alfonso Garlando, which has been making high-quality leather shoes for 50 years, and ogled the window displays at midcentury furniture gallery Robertaebasta.
Explore the vibrant streets of the Brera neighborhood.
Photo by Michelle Heimerman
“You should make some time to see all of the beautiful exhibitions that are always going on in Milano,” Neri says. “Then you should also take advantage of the opportunity to see some historical sites, for example, the Last Supper.” Just be sure to book far in advance if you want to see Leonardo da Vinci’s masterpiece inside the Basilica of Santa Maria delle Grazie. (Tickets are released in three-month blocks, and they go on sale one and a half to two months ahead of each three-month period; they tend to sell out quickly.)
After exploring Brera, you have numerous options for dinner throughout the city. For a classic Milanese restaurant experience, Neri and Akriti recommend Langosteria—the trendy restaurant group runs a handful of seafood spots in Milan, Liguria, Paris, and St. Moritz—and Giacomo Bistrot, which has a refined Old World atmosphere in the city’s center.
Al Matarel serves Milanese classics.
Photos by Michelle Heimerman
“When I want to enjoy classic Milanese dishes like risotto alla milanese [with saffron] or cotoletta alla milanese [the bone-in, buttery veal cutlet], I’d head to Antica Trattoria della Pesa, Ratanà, Trattoria Milanese, or Al Matarel,” Amorena says. Personally, I can vouch for Ratanà in the Porta Nuova neighborhood, where acclaimed chef Cesare Battisti takes a contemporary approach to traditional Milanese cooking. If you go, head up to the rooftop pool bar at Ceresio 7 for an aperitivo first, then walk 15 minutes through up-and-coming Isola, passing by the Bosco Verticale, a pair of plant-covered sustainably minded residential towers by visionary architect Stefano Boeri.
Friday: A deep dive into the city’s design scene
Architecture fans should head to Villa Necchi Campiglio.
Photos by Michelle Heimerman
Every April, Design Week—anchored by the Salone del Mobile, the annual furniture fair where designers debut their latest creations—animates the city with open houses and gallery openings, exhibitions, and events, but architecture and design fans will find plenty to do year-round.
Villa Necchi Campiglio is a pilgrimage site for fans of 20th-century architecture. Designed by Piero Portaluppi for wealthy industrialist sisters Nedda and Gigina Necchi (and Gigina’s husband Angelo Campiglio), the home is a masterpiece of 1930s rationalist design with a large garden, pool, and tennis court right in the center of the city. Now run by the Fondo Ambiente Italiano, a nonprofit organization dedicated to preserving historic places, the villa has been maintained as it was when the sisters lived there, with some works of art added later. If it looks familiar, you might have seen it in Luca Guadagnino’s film I Am Love or Ridley Scott’s House of Gucci.
For lunch, Neri and Akriti recommend the Salumaio di Montenapoleone in the courtyard of the Museo Bagatti Valsecchi, a house museum in the chic Quadrilatero della Moda. “If you’ve never been to Milan, that’s an iconic experience. Because how often do you dine in such a beautiful courtyard? I mean, it’s stunning,” Akriti says. You might also want to visit the museum upstairs to see the Renaissance art and armor collected by the Bagatti Valsecchi counts.
Castello Sforzesco is a medieval fortress in the verdant Parco Sempione.
Photos by Michelle Heimerman
A 20-minute walk through the Quadrilatero della Moda and Brera will bring you to Parco Sempione, the city’s green lung. Pass through the courtyard of the Castello Sforzesco and walk a few minutes to reach the Triennale Milano, the city’s design museum. Check out the temporary exhibitions and the permanent installation of Casa Lana, an apartment designed by Ettore Sottsass, one of the founders of the Memphis Group (a radical Italian design collective founded in 1980). Don’t leave without stopping by the shop, which has an excellent selection of design-focused books, posters, and even 3D printed jewelry.
“I think the perfect day in Milan is balancing the fancy classic chic, which is really Milanese, with something alternative, young, cool, fresh, and not just being stuck in one world,” says Akriti. In that spirit, dinner tonight will be at hipster hangout Erba Brusca in the city’s southern outskirts, where the vegetable garden dictates what’s on the menu and you can savor one of the city’s most affordable tasting menus outside in a garden reminiscent of a low-key outdoor patio in Brooklyn. If you want a nightcap afterward, take a taxi to the hopping Navigli neighborhood and stop by boho-chic MAG Café for avant-garde cocktails or the lively Rita’s Tiki Room for tropical drinks.
Saturday: Contemporary art and international cuisine
Retro Milanese café style at the Wes Anderson–designed Bar Luce in Fondazione Prada
Photo by Andrei Antipov/Shutterstock
On the city’s southeastern edge, the formerly industrial Porta Romana neighborhood is undergoing a radical transformation as the sustainably minded site of the Olympic Village, where 1,300 athletes will be housed. After the games, it will be transformed into student housing.
Today, you can take the metro there to visit a long-standing pillar of the neighborhood: Fondazione Prada. Housed in a former brewery reimagined by OMA, the studio led by famed architect Rem Koolhaas, it displays contemporary art installations by Louise Bourgeois, Jeff Koons, and Walter De Maria, as well as temporary exhibitions. Every Saturday and Sunday, the foundation offers free guided tours in English and Italian (be sure to book a spot in advance). Before or after the tour, stop by Bar Luce, the on-site café dreamt up by Wes Anderson.
For a break from pasta, Neri and Akriti recommend Ba Restaurant for “Hong Kong–level dim sum” or the omakase at Ronin in Chinatown. “It’s an incredible experience because it’s a full townhouse that has been converted,” Akriti says, explaining that there’s an izakaya on the ground floor, sushi and robata on the second floor, omakase and karaoke on the third floor, and a cocktail bar on the top floor. “These are the kinds of things that really make Milan what Milan is.”
Sunday: Join the Milanese . . . on Lake Como
Reserve a table or spend the night at the classic Passalacqua hotel on Lake Como.
Photo by Stefan Giftthaler
According to Neri and Akriti, one of the best things about Milan is its strategic location. Within a couple of hours, you can be by the sea in Liguria, in the Dolomites or the Swiss Alps, or on the lakes. “It’s absolutely crazy how much you can access—and actually the typical Milanese lives this way,” Akriti says. “I mean, we are never here on the weekends. The city empties out because everyone is heading off.”
If you only have time for a day trip, consider going to Lake Como, which is an hour away by train. Once you reach Como, hop on the ferry to visit quaint towns like Bellagio or arrange a private boat tour through Imago Artis. Along the lake’s shores you can see lavish villas built by Milanese nobles and now inhabited by the rich and famous (George Clooney included). One that’s worth visiting is the Villa del Balbianello, where some scenes from 007: Casino Royale and an episode of Star Wars were filmed. The gardens are beautiful, but it’s worth joining a guided tour of the home’s interiors to learn about its last owner, an intrepid explorer who went on expeditions to Antarctica and collected artifacts on his travels in Africa and South America. A Bond-like figure, he even had secret escape tunnels.
Where to stay
Neri and Akriti’s boutique hotel, Vico Milano, is a stylish seven-room hideaway on Corso Genova full of midcentury furnishings, Moroccan rugs, and bespoke design elements. Staying there feels more like visiting the home of your chic Milanese friends than checking into a typical hotel.
If you want to spend a night on Lake Como, splurge on a room at Passalacqua, the ultra-luxe boutique hotel in one of the lake’s grandest 18th-century villas. Run by Valentina De Santis and her family, who also own the Grand Hotel Tremezzo, it’s the ultimate getaway for sophisticated Milanese.
