We’re Jack and Linda, a retired couple from the U.S. who decided to spend our golden years in Milan, Italy. When we first told friends we were moving here, they were surprised—wasn’t Milan too fast-paced for retirement? But we’ve discovered that the city offers the perfect blend of culture, convenience, and everyday pleasures. Here’s what a typical day looks like for us.

Morning: Coffee and the Market

Our mornings begin at the café down the street. Italians don’t linger over giant mugs the way we used to; instead, we stand at the counter, sipping cappuccinos and munching brioche. By now, our barista, Marco, greets us with a cheerful “Ciao, Jack! Ciao, Linda!” as if we were lifelong regulars. It makes us feel like we belong.

Afterward, we often head to the neighborhood market. At Mercato di Via Fauche, Linda always ends up chatting with the tomato vendor, who insists on teaching her new Italian phrases while tossing in an extra handful of basil. Meanwhile, I hover at the cheese stand, eyeing the fresh burrata. Carrying home our bags of food never feels like a chore—it’s part of the rhythm of life here.

We’ve also had our share of shopping mishaps. Early on, Linda picked up a peach to inspect it, just like she used to do back home. The vendor rushed over, wagging his finger, saying, “Signora, non toccare!” (“Madam, don’t touch!”). Mortified, she apologized in clumsy Italian, and he carefully chose the fruit for her. Now we know—you point, and they pick. These small lessons have made us laugh, and they’ve also helped us feel more connected to daily Italian life.

Midday: Exploring the City

Afternoons are often our time to explore. Sometimes we walk to the Brera district, where cobblestone streets hide little galleries and shops. Other times, we wander into museums or sit quietly in Parco Sempione, gelato in hand, watching the world go by.

One afternoon, we decided to visit the Duomo rooftop. While Linda marveled at the sea of spires, I got a bit too close to the edge, and she blurted out, “Jack, don’t make me retire alone in Italy!” The Italian family next to us laughed, and the father said in English, “Better listen to your wife.” It was one of those moments where humor, travel, and human connection all came together.

Lunch Like Locals

Lunch has become a highlight. Many trattorias still offer the pranzo di lavoro—a two- or three-course fixed-price menu. For under twenty euros, we’ll have risotto alla milanese, a second dish, and, of course, wine. On quieter days, we make lunch at home: fresh bread, mozzarella, sun-ripened tomatoes, and olive oil. Simple meals here feel like feasts.

Afternoon: Settling Into Life

The afternoons often involve the “ordinary” side of retirement. Some days we tackle errands—banking, post office visits, or waiting for the plumber (always later than promised). Other days we attend Italian classes. Once, Linda accidentally asked our teacher if the bus was married instead of whether it was crowded. The whole class erupted in laughter, and she laughed hardest of all.

These little stumbles have helped us connect—not just with the language but with people. We’ve made friends through the American Women’s Club and a local book group. Aperitivo evenings with Negronis and snacks have become part of our weekly rhythm.

Evening: Food and Culture

Evenings are when Milan comes alive. Some nights, we dress up and go to La Scala for the opera—it still feels surreal to say that. Other nights, we grab pizza at our local osteria or enjoy aperitivo that casually turns into dinner.

And sometimes, we simply stroll. There’s something magical about walking past the Duomo at night, when it glows against the sky. We always remind each other, “We actually live here.”

Weekends: Beyond the City

Weekends often mean day trips. Lake Como is less than an hour away, perfect for a lazy afternoon. Florence and Venice are close

enough for overnight getaways, and the Alps are practically in our backyard. Travel, once a big undertaking from the U.S., now feels as simple as hopping on a train.

Why Milan Works for Us

For us, retirement in Milan isn’t about slowing down—it’s about living fully. Yes, there are chores, language hurdles, and the occasional bureaucratic headache, but even those feel like part of the adventure.

Every day brings small surprises, like a kind word from a shopkeeper, a laugh over a language slip-up, or a new corner of the city discovered on a walk. Retirement here isn’t what we once pictured—but it’s more rewarding than we ever imagined.

Looking Back, Looking Forward

Back in the States, we always imagined retirement as a quiet routine—golf for Jack, gardening for me, maybe visiting the grandkids now and then. Nice enough, but predictable. Here in Milan, our days are anything but predictable. Some mornings are easy and familiar; others throw us into new situations that test our patience and make us laugh.

Instead of slowing down, we feel like we’re still learning, still growing, still discovering. That, we think, is the real gift of retiring abroad—not just living in a beautiful place, but having the chance to start a brand-new chapter together.