Adjusting to Life in Italy: From Chicago to Milan

After spending a year in Rome for a study abroad program at 19, I spent the next decade fantasizing about coming back. I longed for La Dolce Vita: epic European summers spent sipping spritzes and eating pesto pasta by the sea, letting my hair blow in the breeze as I sat pretty on the back of a handsome Italian man’s Vespa. Fast forward and I did it. I moved to Italy! But as it turns out, adjusting to life in Italy is far more complex than my dreamy fantasy.

Here’s what the real transition from Chicago to Milan has been like for me: the culture shocks, the curveballs, and the slow-building joys of starting over in a new country.

First Impressions

Don’t get me wrong – I knew moving to Italy would be hard. I just didn’t know how hard it would be at times.

For instance, no one prepared me for the psychological (and physical) toll of dealing with the Questura (immigration office) for the never-ending visa appointments. One visit feels like five: you’re shuffled between officers who tell you different things depending on who you’re assigned to – and forget about having the interaction in English. There’s nothing like the adrenaline rush of arriving and realizing your entire legal future in Italy rests on your level-A1 Italian and a few mystery documents you’re told to bring “just in case.”

Credit: Helena Jankovičová Kováčová via Pexels

Then there was the pain in my bank account when I learned that an apartment deposit means three months’ rent upfront plus a percentage of the annual rent as an agency fee. Compare that to one month’s deposit and usually no agency fee for the renter in the U.S., and I was in sticker shock.

And don’t even get me started on public transport. I hit my third sciopero (strike) within my first three weeks of arrival, all while trying to make it to appointments around Milan in the thick of summer. Thank god for good walking shoes – and cold showers.

Despite all of the hurdles, I leaned into these cultural differences even more. And honestly? The positives outweigh the chaos for me. From an adventurous perspective, I can’t complain about the travel perks I take advantage of living abroad. With Milan’s central location I can spontaneously spend my weekends in the mountains skiing or swimming in the sea. 

But I’ve also learned to reset my pace. For example, instead of getting frustrated with a last-minute strike, I’m learning to take it in stride: to expect the unexpected and embrace the idea of slowing down. While it can be hard for a high-strung American to slow down, I am seeing its benefits both physically and mentally. 

Food, Routines, and a New Pace of Life

At work, the cultural shift and mindset to slow down is just as real. When I’m stressed about a project, the response isn’t “lock in and push through.” It’s: let’s get a coffee first. Let’s breathe. Then, we’ll figure it out. In the U.S. I would’ve viewed a coffee break as a delay, a distraction. Now I see it as a necessary touchbase to calm down and take a beat before diving into problem-solving. 

Speaking of coffee, in the U.S., my mornings started with a gallon-sized coffee – productivity in liquid form. In Italy, it’s all about simplicity and quality: a small yet potent espresso, sipped slowly, often with conversation.

Credit: Aleksandra Pacicco via Pexels

The same goes for food. Yes, I eat pasta almost every day. No, I haven’t gained weight. (It still feels like a miracle.) Most likely because I am typically eating small portions of very fresh food made with few ingredients while surrounded by many friends. Meals last hours and the food and time together is genuinely savored.

Some adjustments are still ongoing. For example, I’m currently enduring the soul-draining process of getting an Italian driver’s license. Try answering questions like: “Can you drive a truck over 3.5 tons on a highway at 90kph in the rain?” in a second language.

Language Learning: Humbling and Hilarious

As you can imagine, the language is still an ongoing challenge. Thankfully, Milan is so international that speaking Italian sometimes feels like a “nice to have,” not a necessity. But when I do use it, the effort is usually appreciated – and occasionally hilarious.

I’ll never forget a trip along the Cilento coast when my friends shouted “Facciamo un bagno!” before diving off the boat. At the time, I thought they were all suggesting we…go to the bathroom in the sea. I mentally clocked it as a strange cultural habit. Only months later did I realize it means “let’s go for a swim.”

Credit: Bianca Mallia via Pexels

Even now, I make plenty of slip-ups. Just last week, I may or may not have told my coworkers how much I love burro di arancia (orange butter) instead of burro di arachidi (peanut butter). 

The saving grace is being surrounded by kind, patient people: coworkers, friends, and my boyfriend’s family, who gently correct me and cheer on my progress. I’ve learned to laugh at myself, and that has made all the difference.

Final Thoughts

Adjusting to life in Italy and moving to a new city as an adult is hard. But the rewards are unforgettable. 

You have to be okay with being uncomfortable. I’m far from my family and lifelong friends, and it takes time to build my community here. It’s an emotional balancing act: staying in touch with my roots while investing in new relationships. But slowly, community forms. Through shared meals, spontaneous invites, work lunches, and language mistakes, I’ve found connection. It’s not instant, but it’s real.

Credit: Nicole Michalou via Pexels

Italy has taught me a deeper appreciation for enjoying and living in the moment, a newfound outlook on happiness, and a healthier pace of life. It’s not always spritzes on a terrace, but sometimes it is. And when it is, it’s that much sweeter. 

I think I found my dream of La Dolce Vita after all.

Sara Bauer

Contributor

Ciao! I am Sara, an American writer and travel blogger based in Milan, where I balance my corporate day job with a passion for exploring Italy’s hidden corners. From budget trattorias to five-star stays, I cover the full spectrum of Italian living - always with a sense of curiosity (and perhaps a Franciacorta in hand). In my free time I love skiing, musical theater, and swimming in the sea. You can discover more of my travel tips and adventures on www.sarainitalia.com and can follow me at @sara.in.italia.

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