Others have gained an appreciation of the city in recent years, too: ultra-wealthy foreigners have flocked to Milan since 2017, when Italy introduced a flat tax on foreign income. International members’ clubs and hotels, including Soho House and Casa Cipriani, have opened or are planning to open new outposts in Milan.
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Still, Milan’s many cultural, historic, food, and night life options haven’t been flooded by newcomers, so the feeling of serendipitous discovery remains a real possibility for visitors. Starting May 11, Milan will be more accessible to Bostonians than ever, as JetBlue launches direct flights from Logan International Airport.
Milan is decently connected with public transit, though locals save time by hopping on e-bikes via operators such as Lime or Dott or using ride-share apps. To minimize logistical stress, stay in the Centro Storico, meaning historic center, or for more affordability, nearby in a neighborhood such as Zona Risorgimento or Isola.
Here is an itinerary of my four perfect days in Milan, a long weekend full of food, art, history, and, of course, wine.
The typical Italian breakfast is simple: a cappuccino or espresso and a pastry. (Cigarette, optional.) Pasticcerie, or bakeries, are abundant across Milan, but for a particularly indulgent experience, head to Marchesi 1824 on Via Santa Maria Alla Porta in the historic center, where the cafe’s original outpost has stood for two centuries.
Now owned by Prada, Marchesi 1824 serves gorgeous little treats including maritozzi — fluffy buns filled with whipped cream — and cornetti, similar to French croissants but softer, and filled with pistachio, chocolate, or plain cream.
Marchesi 1824 at Galleria Vittorio Emanuele II in Milan.Adobe Stock/Andrei Antipov
Continue feasting with your eyes, if not your stomach, with a visit to the nearby Chiesa di San Maurizio al Monastero Maggiore, a 16th-century church whose walls are covered in colorful, intricate frescoes painted by one of Leonardo da Vinci’s disciples, Bernardino Luini.
Next, stroll to the Pinacoteca di Brera, Milan’s premier art museum, to see Italian masterpieces by Caravaggio, Bellini, Tintoretto, and others. A 15-minute walk away is the Ambrosiana, a library and art gallery where you’ll see the full-scale drawing that Raphael made for The School of Athens, and original pages from da Vinci’s 12-volume Codex Atlanticus.
After consuming so much art, you’ll need to recover your other senses, and for this, I recommend a late lunch at Piz. Bear with me here, and don’t judge a book by its cover. Located smack dab in the middle of the historic center, Piz is no hidden gem. Its walls are painted in bright yellow, it’s often packed, and on arrival, you’ll receive a free glass of prosecco. The menu is short and the pizzas fantastic (and a bargain, at $9 to $15 US dollars). Choose from margherita, marinara with garlic, white pizza with poppy seeds and chives, and a pizza of the day.
Visitors look at a painting in gallery Pinacoteca di Brera.JAROSLAV MORAVCIK/Adobe Stock
Cap off a day of sightseeing with a visit to the city’s top tourist attraction, just down the street from Piz: the Duomo di Milano, a Gothic-style cathedral that was built over nearly six centuries, beginning in 1386. Every time I pass the Duomo, I am awed by the scope and complexity of human collaboration that was required to build it. A combination ticket provides access to the cathedral and the rooftop, which you can reach either on foot or via elevators. Cue spectacular city views. On most days, the last entry is at 6 p.m.
Italians are so adept at the transition from afternoon into evening that they have a name for it: aperitivo. After visiting the Duomo, grab a drink next door, at Camparino, a bar that has been mixing the Campari Spritz to exacting standards since 1915.
Galleria Vittorio Emanuele IIAdobe STock
Spritz in hand, enjoy the free crackers and olives, along with the view as the sunset paints the Duomo’s twisty spires and white-pink marble facade with brilliant shades of gold, pink, and orange.
For dinner, head to Pane al Pane Vino al Vino, a trattoria serving Lombardian cuisine that’s popular with locals and dishes up pure comfort on a plate: risotto with tender veal falling off the bone; Milanese cutlets, similar to schnitzel; and tortelli with porcini mushrooms or butter and cheese. In Italy, the best way to end the day is with a full and happy stomach.
Piazza del Duomo at night.Georgios Tsichlis/Adobe Stock
After breakfast, hop on a 50-minute, $7 train to Bergamo, the city on a hill.
Once a prosperous jewel of the Venetian empire, Bergamo’s historic center is compact but full of fascinating sights, including Museo della fotografia Sestini, a museum about the history of photography located inside a former convent, and the Rocca di Bergamo, a 14th-century fortress housing a history museum.
To reach the historic center, called Città Alta, you can walk all the way up the hill or take a funicular. For the latter option, enter “Funicolare Città Alta” in your navigator and follow the map. At the top, you’ll find Via Bartolomeo Colleoni, a street lined with restaurants, gelaterias, and boutique shops that leads to the main plaza.
On my visit to Bergamo, I enjoyed the 17th-century Palazzo Moroni, a former private residence decorated with decadent Baroque frescoes. The terraced gardens in the back are an oasis hidden from the bustle of the street. I’d also recommend the Basilica di Santa Maria Maggiore, a Romanesque church in the old town’s center.
The real charm of the old town of Bergamo lies in meandering its centuries-old streets, passing colorful houses with old-timey shutters, turning uneven corners, and coming upon long-range vistas of the countryside.
Centro StoricoKavalenkava Volha/Adobe Stock
In the evening, return to the southwest part of Milan’s historic center for dinner at Vico Milano, a boutique hotel and reservation-only restaurant in a peaceful courtyard hidden from street view by a gate and a nondescript door. (Wave a hand at the buzzer for entry.)
Vico was built on the site of a former bike factory and retains some of its original industrial feel with exposed concrete walls and stairs. Moroccan rugs and tiles, vintage furniture, and Greek marble add a cozy balance. The food is a sophisticated take on Italian classics and includes Milanese-style risotto with a hearty wild boar ragù, tender ossobuco with potato purée, and lobster alla catalana. On my most recent visit in March, I delighted in the oversized ricotta-spinach raviolo prepared according to the recipe of the owner’s mother.
If you still have energy after a full Italian dinner — I usually don’t — Vico is a short walk from the Navigli district, a lively night life area centered around two canals. You’ll find dozens of bars, live music venues, and clubs to choose from.
The Naviglio Grande canal in Milan.Adobe Stock
One of Milan’s most famous former residents is Leonardo da Vinci, who lived in the city for about 20 years while serving in the court of the ruthless politician and short-lived Duke of Milan Ludovico Sforza.
In Milan, da Vinci painted The Last Supper, still on display at the Cenacolo Vinciano Museum. Tickets become available a few months in advance and sell quickly, so be prepared. Next door to the museum is the church and convent where da Vinci painted The Last Supper: the Basilica of Santa Maria delle Grazie. This UNESCO-listed site is a lovely place for contemplation and is open to visitors without booking. For a deeper dive into Da Vinci’s achievements and follies, I recommend joining a walking tour (I did Isa Gama’s on Airbnb Experiences).
One of the best neighborhoods for glimpses of Milan’s famous street style and people-watching is Porta Venezia, adjacent to the historic center. Grab a spot in the sun at a sidewalk table at Pasta Fresca Brambilla, a no-frills restaurant serving freshly made ravioli, lasagna, tagliatelle, and more.
Walk off the meal by weaving through Porta Venezia’s streets, which are lined with stunning buildings in the Liberty style — Italy’s version of Art Nouveau — to Villa Necchi Campiglio, a 1930s house-museum once owned by the dynasty behind Italy’s equivalent of Singer sewing machines. I could spend hours wandering through the rooms here, which are filled with period furniture and delightful vintage objects.
It’s always 5 o’clock somewhere. That somewhere might be Piazza Morbegno, a plaza in NoLo, an up-and-coming neighborhood that’s a 20-minute subway ride from Porta Venezia. At Piazza Morbegno, you’re bound to find twenty- and thirtysomethings on the sidewalks with beers or Negronis, whether it’s a Sunday or a Thursday.
I prefer to have somewhere to sit, so I walk a few blocks to Enoteca La Botte Fatale, a natural wine bar with knowledgeable bartenders and a vast Lambrusco selection.
After aperitivo, hop in an Uber for a 15-minute ride to Spore, where the $70, seven-course tasting menu focuses on fermentation and changes every two months. In March, I tried some truly inventive dishes there, including skewers with hake, a pumpkin sando with fermented cabbage salad, and a lamb’s head served with toasted brioche, spicy chimichurri, and charred lemon.
Start the day with a change-up to the cornetto-coffee routine. Consider: Pasticceria Cucchi, a classic Milanese bakery with options such as yogurt with homemade granola and berries, and pancakes with Gianduja and bananas; Loste Café, which offers filtered coffee and pastries with fillings including pear and miso caramel; or Ammu, a Sicilian cafe with several locations serving cannoli and brioche buns with gelato or granita, the Sicilian ancestor of Italian ice. No better excuse to have ice cream for breakfast than a weekend in Milan.
For a nature break, drive or take a 45-minute train to the city of Como or to Lecco, a less crowded alternative with good transport connections to towns on the eastern leg of Lake Como and to hiking routes. If you’re in the city of Como for a brief stay and want to catch some spectacular views, take the funicular that rises 1,600 feet to Brunate.
Lake ComoAdobe Stock
For Lake Garda, rent a car or take the one-hour train to Peschiera del Garda or to Desenzano. I love the Parco Termale del Garda, a park with a naturally heated thermal lake that’s a 15-minute drive from Peschiera del Garda. The thermal park is open until 11 p.m. most days and 1 a.m. on Saturdays. You can stash your things in a locker and laze on the chaise longues surrounding the lake between dips. Once the sun sets, string lights set the mood.
For a more active day, arrive at the lakes early and ferry hop among the lakeside towns that abound with cobblestone streets, picturesque nooks, and gelato shops, such as Bellagio or Varenna in Como, or Sirmione or Malcesine in Garda.
From the city of Como, you can also easily reach Villa Balbianello, the setting for Casino Royale, and Villa Carlotta, an art museum with gardens. Be sure to book entry tickets in advance.
A balcony overlooking Lake Como in the Villa del Balbianello.Adobe Stock
If you have the time, check out the Lake Como Greenway, a walking and cycling path that runs through several villages and offers gorgeous vistas, or one of the free beaches around the lakes, called spiagge libere in Italian.
At the end of the day, I love to watch the sun sink behind the mountains. It’s one of the world’s greatest treats — and even better with an Aperol spritz. Cin cin!
Valeriya Safronova is a freelance journalist who lives in Vienna and writes about travel, culture, internet trends and beyond. Send comments to magazine@globe.com.