Solo in Italy: First Stop, Milano

Friday, October 31, 2025

A Year of Traveling Alone

This past year, I’ve taken up solo travel. Following an unaccompanied trip to Madrid in October 2024, I discovered that I actually enjoy traveling alone.

This summer, I spent five days in New York City without a travel partner—and just like in Madrid, I learned that independent travel suits me. You can walk where you want, when you want; eat what you want, when you want. Absolute freedom.

From Madrid to Milan

So, I decided to take it a step further this fall. Now I find myself in Milan, Italy, for four days, followed by ten days in Florence. Milan is completely solo, and in Florence, I’ll be joining a group from Road Scholar—none of whom I’ve ever met.

I suspect my desire for all this “lonesome” travel could use some psychoanalysis. But that’s for another day (and probably not worth sharing anyway). For now, I’ll just share my journey with anyone curious enough to follow along.

Cultural or Spiritual?

My good friend and pastor, Ron Brooks, asked whether this trip is a spiritual or cultural quest. My quick answer was “cultural,” and that was the original intent.

However, I think there’s more to it than that. It’s likely a blend—part cultural, part spiritual, maybe even self-discovery. I won’t pretend to have the answer now, but I imagine it will unfold as the journey continues.

The Journey to Milan

I left Des Moines, Iowa, on Thursday, October 30, and arrived in Milan the following afternoon.

I’ve said it before and I’ll say it again: I think I’m getting too old for overnight flights. During the 8+ hour leg from Chicago to Milan, I finally understood why people lose their minds on airplanes. I couldn’t sleep, I grew restless after too many episodes of The Diplomat and a few rounds of Tetris, and I couldn’t even focus on my Hemingway book.

But alas, I made it—without assaulting anyone, especially the poor baby who wouldn’t stop crying. I truly felt for its exhausted parents.

First Impressions and First Mistakes

After landing, I got completely ripped off by a cab driver on the way to the city center—my own fault for being too tired to navigate public transit. I decided to forgive myself, take a nap and a shower, and then hit the streets for some exploring.

                Finding dinner was harder than expected; most restaurants seemed to offer the same fare—pasta, pizza, fish. Tonight, as long as there was wine, I didn’t care. I ended up at a quaint spot called Meat Grill (how’s that for creativity?) and ordered Caprese Ravioli. Delizioso. 

What’s Next

Tomorrow, I’ll join a guided walking tour of Milan’s city center, including a visit to see Leonardo Da Vinci's Last Supper. What’s next after that? Who knows—but I’m sure I’ll find plenty to fill my time.

I’m going to love this place.

Buona sera! 🇮🇹