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Milan is often overlooked when people travel to Italy, but it’s a city of charming contrasts: old meets new; grit meets grace; style meets simple. With enough time (and the right guide), you’ll uncover it’s beauty; but remember, Milan is a lady - she doesn’t reveal herself all at once.
While you can visit the Duomo or The Last Supper, try to embrace the Italian concept of Il Dolce Far Niente, or “the beauty of doing nothing.” Time is best spent wandering down the beautiful shopping streets of Montenapoleone, peering through the open entryways of the palazzos, enjoying aperitivo on the chic streets of Brera, sipping a morning espresso then walking through Park Siempone, savoring fresh pasta and fine wine during lunch, or just gawking at the beautiful people.
To top it off, the city has an escape to the famed Lake Como, less than an hour away - which we will take advantage of.
Brera & San Marco
Of all of the neighborhoods, I find Brera to be the chicest and most charming.
Enjoy a coffee at 10 Corso Como then snake down Corso Garibaldi and Via San Marco.
Line up early at lunch for pasta at La Latteria - cozy restaurant with no reservations, which recently reopened. Check their dates and hours ahead of time.
Around 6, the neighborhood begins filling up for aperitivo (think: happy hour). N'Ombra de Vin or Fashion Cafe will always have an atmosphere.
Via Montenapoleone
Think Rodeo Drive, but better. In 2024, it was named the most expensive street in the world. So either do some shopping or window shopping here.
After deciding against buying a $4,000 sweater, take yourself to lunch at Il Salumaio di Montenapoleone or Paper Moon Giardino -make a reservation.
Navigli
You may not have known that Milan has a canal district. Restaurants and bars spill out onto the streets lining the canal, making this perfect for afternoon wine. If you need a specific spot, I'd recommend Mag Cafe.
This is a neighborhood where I also discovered a local artist, whose work is framed in my home.
Porta Venezia
This neighborhood leans vibrant and fun over chic and sophisticated. Don't let that stop you from visiting though. There are still great shops and restaurants. Nearby, you'll find Bar Basso, where the negroni sbagliato was invented.
Oh, did I mention it is also the gayborhood?
Galleria & Duomo
This is going to be the most crowded and most touristy part of the city. However, you must see these architectural works.
After wandering around, stop for a drink in Camparino, which has views of the Galleria. For any last minute shopping needs, visit Rinascente - a large department store.
Parco Sempione
Take a stroll through the park or go visit Castello Sforzesco. There is also a loop around the park that's perfect for a long morning walk or run.
You can also head north to Chinatown and grab a drink at Cantine Isola dal 1896 (a great wine shop that also pours glasses) or Da Orient (vintage store + bar).
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