Italy
I hadn’t planned on falling for Milan.
As a tech consultant based in Toronto, I’m often on the move—conferences, client meetings, hotel lobbies that all blur into each other. So when I was invited to speak at a digital innovation summit in Milan, I figured I’d fly in, do the talk, and head home. But a few late nights scrolling through travel blogs changed my plan. One site in particular, MilanoStyle.com, stood out—curated by travel writer Celia Abernethy, who, unlike most influencers, actually lives there. Her writing felt genuine and practical, especially for someone like me who wanted to visit Milan and see the city without feeling like a tourist. I even reached out to her to ask questions about things to do in Milan, and to my surprise, she replied with a few insider tips. That sealed it: I was staying an extra three days.
A Stylish Start
My first full day of exploration started in Brera. This charming district feels like a village tucked inside a fashion capital—cobblestone streets, boutique galleries, and espresso bars where locals actually linger. Following one of Celia’s suggestions, I wandered into Princi near Porta Garibaldi. Yes, it's a chain—but even the Italian chains feel special. There’s something different about the energy here. I stood at the marble counter, sipping a perfect espresso, surrounded by Milanese professionals and stylish retirees alike, all weaving effortlessly between tradition and trend. I stood at the counter near the window watching well-dressed Milanese start their day, somehow both effortlessly cool and unmistakably polished.
After breakfast, I headed to the Pinacoteca di Brera. Even if you’re not a typical museum-goer, this place will pull you in. The works of Caravaggio, Mantegna, and Raphael are displayed in a way that feels intimate, not overwhelming. Outside, I passed a string of antique shops and modern design studios, where I almost bought a hand-crafted Murano glass lamp (regret not doing so, honestly).
Living the Piazza Life
Later that afternoon, I made my way toward the Duomo. As much as it appears in every guidebook, seeing it in person is something else. I took the elevator up to the rooftop terraces (worth every cent) and walked among the spires. Milan stretched below me—elegant, ordered, yet vibrant. I was grateful I didn’t rush this trip.
In her email, Celia had recommended an aperitivo at Camparino in Galleria, a historic bar in the Galleria Vittorio Emanuele II. It’s fun to watch the bartenders shake up the cocktails, and the vintage décor is authentic, not a phony replica. I sat under the shade of the terrace canopy with a classic Campari Spritz, looking down on the plaza. The Campari Spritz is bitter, bright, the people-watching here is next-level. It was like watching a live theater of style, symmetry, and movement.
A Design Lover’s Dream
One of the highlights of my trip was visiting the ADI Design Museum near Chinatown. As someone who works in tech, I found it fascinating. The permanent collection includes original Olivetti typewriters—beautiful, functional pieces of early innovation—as well as iconic furniture, prototypes, and even a few classic Ferraris. The exhibits connect Italian design to everyday life in a tactile and timeless way. It made me think about how design—when done right—can elevate even the most practical tools into works of art.
That evening, I went to the Navigli area and had dinner at Posto di Conversazione. I ordered the cotoletta alla Milanese, perfectly crisped and golden. The area was lively but relaxed—people out enjoying the evening, sipping wine along the canals. I wandered a bit afterward, soaking in the atmosphere. It felt good to be surrounded by people simply having a nice time, unhurried and unfiltered.
The Perfect Day Trip
I wanted to take a day trip to Lake Como on my final day. I avoided the usual Bellagio–Varenna circuit (as recommended) and instead explored Menaggio, a quieter town on the western shore. I had lunch at a lakeside spot called La Grolla, where I tried lavarello, a local lake fish that was fresh, delicate, and lightly grilled. I walked without a plan in the town center and felt so relaxed. The cobblestone town square and little lanes are cute and picturesque.
A Few Stylish Souvenirs
Back in Milan, I spent my last afternoon doing some light shopping. A handmade leather wallet for my wife. A couple of chic accessories for my daughters (teenagers, so I double-checked they were “cool enough”). And a shirt for myself that I’ll probably wear too often.
I thought about going to Serravalle Designer Outlet, which I’d read about on MilanoStyle.com, but realized I didn’t have the time to do it right. That’s a full-day adventure I’d rather share with my family anyway. Next trip, for sure. They’ll love it.
Final Thoughts
Milan isn’t showy. It doesn’t try to impress you. It just is what is defined, real, and full of small details that add up to something quietly unforgettable. It’s a city that respects your intelligence and rewards your curiosity.
If you ever find yourself here, even if it’s just for work, I highly recommend staying a little longer. Read a few local blogs. Ask for help. You never know where a well-written tip or a kind response might lead you.
Thanks to a spontaneous decision and a bit of guidance from someone who knows the city inside out, I came home with more than a few souvenirs—I came home inspired.
