Milano with Teen & Dog: A Stylish, Relaxed Day in the Lombardy Capital

After a morning of warm hospitality in Folgaria and an adrenaline-laced drive down winding mountain roads, we rolled into Milano late morning. This wasn’t going to be the kind of trip where we tick off every landmark in a guidebook. I’d been to Lombardy’s capital before, and this time we were here for something different — a teen- and dog-friendly Milan day, done our way.

Our first stop wasn’t the Duomo or the Galleria, but Parco Sempione, where Hana, our Shiba Inu, could finally stretch her legs after hours in the car. She ran, sniffed, and looked utterly pleased with life — the canine version of that first sip of coffee in the morning.

From there, we checked into our suite at the Milano Verticale | UNA Esperienze. For Hana’s comfort (and the hotel’s peace of mind), we always travel with a portable, lockable kennel she’s already used to. It keeps her safe and relaxed while we step out — a travel-with-dog tip I swear by.

With Hana settled in, we headed out for the most Milanese of strolls: from the Teatro alla Scala, through the Galleria Vittorio Emanuele II, and toward the Duomo. The sunlight spilled into the galleries, bouncing off marble and glass, and we ended up at the Rinascente Milano rooftop for a cocktail overlooking the cathedral’s spires.

Of course, traveling with a 13-year-old means factoring in trend-driven stops. On this trip, that meant the largest Sephora in Milan on Corso Vittorio Emanuele II. My daughter browsed with the intensity of an art critic, hunting for influencer-approved products, muttering about how the “Sephora kids” had already cleared the shelves. I stocked up on my own beauty must-haves — because Milan is no place to skip self-care.

Dinner was at a small, bustling spot in the tourist-heavy center — probably not the most refined place in town, but brimming with atmosphere and serving dishes that felt homemade. Sometimes, the charm is in the imperfect.

As the evening cooled, we collected Hana for a walk in BAM – Biblioteca degli Alberi Milano. There, she had what every Shiba owner knows as “zoomies” — bursts of wild, joyful energy that send her sprinting in crazy circles, ears back, eyes bright, the happiest little whirlwind in Milan.

By the time we returned to the hotel, both child and dog were out cold, the city lights winking beyond the window. It had been the perfect mix of style, comfort, and spontaneity — proof that Milan can be enjoyed without rushing, and with four-legged and teenage travel companions in tow.