Experience the unplanned enchantment of an afternoon in Milan with friends. From the Duomo to Sforzesco Castle, savour the magic of this Italian city.
They say the best adventures are the ones you don’t plan. While I am the living and breathing embodiment of a Virgo who likes to plan literally everything and anything I can (just ask my poor mother about our 2016 trip to Paris), I have worked really, really hard to adopt the dolce far niente lifestyle that the Italians live by. This is how my afternoon in Milan came about, the only thing planned was to see my Canadian friends living abroad, Maria and her kids, and to go inside the Duomo. We picked a date when I would be in Bergamo, chose a time, and flew by the seat of my pants, Italian-style.
I can now attest to the fact that, surprisingly, a slightly impromptu afternoon in Milan is doable—although you’ll barely scratch even the surface of what the city has to offer (I can confirm that, living in Milan right now and getting the full experience a year after this first visit that I’m writing about). So, while spending at least a few days in Milan is most desirable, the spontaneous decision to visit is better than nothing, and the stunning architecture, delectable food, and lovely city views are enough to whet one's appetite for major northern Italian cities.
A Scenic Train Ride to an Afternoon in Milan
There's something romantic about train travel, isn’t there? It’s always been my preferred mode of transportation—that steady rhythm, the soft hum of conversations around you, and the beautiful scenery flashing by. My journey from Bergamo to Milan was no exception.
Leaving Bergamo at around 9:00 AM, we boarded the train, found two seats, and pulled away from the station bound towards Milan. I found myself mesmerized by the picturesque Lombardy landscape as rolling hills gave way to quaint villages, which turned into a cityscape and, before I knew it, the iconic skyline of Milan came into view. Arriving at Milano Centrale, Milan’s central train station, is an experience in itself. The grandeur of the station, with its art deco architecture and bustling crowds, sets the stage for the adventures that await in the city.
Finding your way from the area for intercity trains to the subway system was a bit of a hike, but we followed the signage and managed to get to the right spot. Here, we purchased the second ticket and headed to our destination at Metro Lines 1 and 3 intersection: Duomo.
The Duomo as Milan’s Crown Jewel
Our first stop was the Duomo di Milano. We arrived at Duomo station, emerging into the bustling Piazza del Duomo, and I was absolutely star-struck. Truly, seeing the towering Cathedral of Milan—one of the largest churches in the world and the largest church in all of Italy—felt like meeting a celebrity. The sight of the magnificent Gothic cathedral amongst the backdrop of the city was breathtaking. My cousin and I walked along the perimeter of the building, my eyes constantly looking up at the towering spires against the clear blue Milanese sky, until we found ourselves waiting in line to enter.
My cousins living in Bergamo had bought me tickets to see the Duomo (along with a gondola ride in Venice, which we had done the day before), and it was one of the most rewarding gifts I’ve received. It probably comes as no surprise that I’m a big fan of experiential gifts that I get to do with people I care about, especially when they involve history, art, and travelling.
Inside, the Duomo was just as awe-inspiring as it was on the outside, with its towering columns and intricate stained glass windows pulling visitors into its embrace. We spent a good amount of time walking around the cathedral, taking in the sights and capturing photos, each click of the camera preserving a piece of the magic that was felt. There really is something so ethereal about these centuries-old buildings, with colourful light pouring in and dancing along the marble floors, grand and imposing statues filling entire niches, and ceilings so high they seem to be reaching directly into heaven.
My friend Maria then arrived with her daughters at the Duomo, so my cousin and I exited the church to join them for the rest of our afternoon in Milan. Now, we were finally in the trusted hands of locals.
Exploring Milan with Friends
Meeting up with Maria and her kids was a highlight; not only had they been living in Milan since the pandemic, but I hadn’t seen them for over a year before that because they live in Edmonton (and I can only travel there once or twice a year). They played the perfect tour guides, showing me some of Milan’s most beautiful spots, and the girls eagerly gave us information about certain buildings and shared their own personal anecdotes about life in Milan. We strolled through charming streets, discovering hidden gems and their local favourites along the way.
We wandered through the fashion district on our way to Maria’s recommended lunch spot, even if just for window shopping. The streets of Quadrilatero della Moda (or ‘Fashion Square’) were lined with elegant boutiques and designer stores, each displaying a testament to Milan’s status as a fashion capital. The energy here was infectious, even if we were just admiring it all from the outside.
A Neapolitan Feast in San Babila
It’s a good thing we did so much walking that morning, because all that exploring worked up an appetite. We made our way to San Babila for the most delicious Neapolitan pizza, at a pizzeria right from Naples. This was a place where Maria had promised to have authentic flavours and the perfect crust, and let me tell you, it did not disappoint. The pizzas were phenomenal—perfectly thin but fluffy crusts with generous toppings of fresh mozzarella, basil, and tomato sauce.
I savoured each bite in between continuing to catch up with my friends. We laughed and shared stories, enjoying the warm, welcoming atmosphere of the pizzeria on the late September afternoon. It was one of those meals that felt like a celebration, pure joy shared with the people you care about. Not to mention how the simple yet rich flavours of the pizza were a testament to the art of Italian cooking, particularly with one of the country’s most famous dishes.
Historical Wonders at Sforzesco Castle
With our hunger satiated, we continued our journey to Sforzesco Castle (Castello Sforzesco). This historical fortress is a treasure trove of art and history, and walking through its courtyard and around its outskirts was a captivating experience. The best part? Exploring these areas is free, making it an accessible adventure for everyone, especially those on a time crunch like we were (we had to get back to Bergamo by evening to catch our return flights to Calabria that same day).
The castle’s imposing walls and beautiful architecture told stories of a bygone era, and we felt a sense of connection to the city’s rich past. Maria’s kids loved running around the courtyard, their laughter echoing against the ancient stone walls, before they would come back and hold our hands. It was a perfect blend of people-watching and exploration, an experience that brought history to life in a tangible way. Oh, and while you’re here, don’t forget to try and spot the castle’s stray cats that can be seen waltzing along the grounds without a care in the world.
Sweet Treats in Sempione Park
Right behind the castle lies Sempione Park (Parco Sempione), a lush, green oasis in the heart of Milan. We headed there for a sweet treat—a refreshing granita for the adults and a gelato for each of the girls. The park’s serene ambiance was a welcome respite from the bustling city streets, and it was here that I told Maria I wanted to come live in Italy for a year. She encouraged me to do so, telling me what it was like adjusting as a fellow Canadian and giving me advice on how I could make it happen (she continued to be an amazing help as I got ready to move and continues to be even now—I’m so lucky!).
We found a shady spot on a park bench to sit and enjoy our icy treats, watching the world go by as we all chatted. Sempione Park is a gem, offering both tranquillity and a vibrant social scene. Families picnicked on the grass, friends played sports, and couples strolled hand in hand. It was a perfect end to our day, a moment to relax and reflect on the wonderful experiences we had shared.
All in All
Milan effortlessly blends history, culture, fashion, and gastronomy—something I’ve come to realize even more now that I am living here for the coming months. Whether you have a day, a weekend, or a week, there’s always something new to discover in this beautiful city. My afternoon in Milan was a whirlwind of unforgettable experiences, a reminder that sometimes the best travel memories come from the most spontaneous plans with the best people.
So, hop on a train to Milan next time you find yourself with a free afternoon and a sense of adventure in northern Italy. Wander through its charming streets, indulge in its culinary delights, and soak up its rich history. I promise that even a brief visit will leave you with stories to tell and a longing to return.
So fun! I sure envy your time and freedom. This make me think I’m working too much. Time to plan a get away!
Loved your spontaneous adventure in Milan! The hidden gems you discovered make me want to explore the city myself.