Italy has been at the top of my travel list for years. The food, the fashion, the history, the drama of it all… It’s always called my name. So when I finally booked my very first trip to Italy, and it happened to be solo, I walked in with high expectations.
Milan didn’t just meet them. It absolutely showed off.
I know I only scratched the surface with one city, but wow, did Milan set the bar high. It was the perfect mix of beautiful, chaotic, stylish, and cold enough to remind me how much I miss fall. I’d walk outside every morning like, “Oh, hey, crisp air… long time no see.”
And can we talk about the fashion? The people in Milan don’t just dress well. They commit. Even the dogs dress better than half the influencers on my feed. I’m convinced I saw a dog in a Moncler sweater and honestly… respect. Milan turns the sidewalks into a runway, and everyone knows their role.
This was also the trip where I learned a lot about myself. Like the fact that I’m capable of figuring out public transportation in a foreign country. Was I low-key terrified? Absolutely. Did Apple Maps carry me on its shoulders like a proud parent? One hundred percent. But in the end, I got around just fine. And when I wasn’t hopping on metros or trams, I walked everywhere. Milan is the kind of city that makes wandering feel effortless.
I highly recommend visiting the Milan Cathedral. It’s the classic postcard moment, the one that makes you feel like you’ve officially arrived in Italy. Then there’s Sforza Castle, which is gorgeous from the outside, especially at sunset when the whole place glows. I didn’t make it inside, but if the exterior is any hint, the inside has to be just as stunning.
And don’t miss Brera. It’s one of those neighborhoods that feels like a warm hug. Cute boutiques, tiny artisan shops, cozy restaurants on every corner. It’s the perfect place to wander around with no plan and let the city charm you.
But the best part of the whole trip? The people I met on my last night in the hostel.
I swear the universe always saves a little magic for the end. I walked in expecting a quiet night and ended up with new friends who made my “Home Alone but make it Milan” trip feel so full. Moments like that remind me why I should travel solo more often. You’re open. You’re curious. You meet people you never would’ve crossed paths with otherwise.
I love having friends from all over the world. I love connecting with people who think differently, live differently, and still manage to click with me. It makes me feel more grounded and more global at the same time.
And if you’re thinking about traveling solo, let me just say this as someone who’s lived it: do it. Seriously. It’s so normal here in Europe, nobody bats an eye, and it might end up being the most freeing thing you ever do. You learn so much about yourself, your habits, your fears, your courage… all of it. And somewhere along the way, you end up meeting people who can turn into real, lifelong friends.
Outside of my magical last night in Milan, one of my favorite places was Mercato Centrale. I know every big city has its own version of a food hall, but this one felt different. It was huge but somehow still cozy. The moment I walked in, it gave me New York energy in the best way.
There were Christmas lights draped everywhere, warm lights glowing from every stall, the smell of food from every corner, and people constantly moving in and out like a living heartbeat. It had that mix of noise and warmth that makes a city feel alive. Add in the cold weather outside, and the whole place felt like a hug.
Solo travel gives you moments like that. Tiny, ordinary scenes that somehow turn into core memories. Moments you can’t plan, but you’re so grateful you showed up for.
So yeah… my first trip to Italy was a win. No regrets. Just lessons, laughter, and a city that gave me more than I expected. Milan, you were the perfect introduction. And trust me, I’ll be back for the rest.
Love always,
American Girl Meets World
*Fun fact*: The Milan Cathedral took nearly six centuries to complete. Six. Hundred. Years. No wonder it steals your breath the second you walk up those metro stairs. It’s literally the longest glow-up in European history.
