I hesitate to say that moving to Italy is the hardest thing I’ve ever done, but honestly, it’s pretty close.

I decided to uproot my life in Boston for a new one in Milan rather abruptly. In the beginning of the summer, I was preparing for another year in Boston: I had a lease I was planning to renew, and enrolled in a graduate degree program that would kick off in September.

But then, in June, a handful of seemingly small nudges from the universe got me thinking seriously (again) about packing up my things and moving abroad.

  • First, one of my best friends told me they were leaving their corporate job (and Brooklyn apartment) for a new life as a snowboard instructor.

  • Then, I had a conversation with a hiking friend who, upon learning that I was an American-Italian dual citizen, posed some version of the question I often get in response: “Then why are you still living here?”

  • And finally, when I texted my roommate about renewing our lease, she informed me that she was actually thinking of leaving to find an apartment of her own.

Welp.

Suddenly, a strong aroma of transition was in the air. Why not embrace it?

I had been mulling the idea of moving to Italy, on and off, for years by this point.

For the uninitiated: I grew up in New Jersey with grandparents who immigrated from Italy to America for a better life, and carried with them the traditions and recipes of their homeland. In other words, my childhood was steeped in red sauce and Catholic guilt.

In 2016, I was lucky enough to study abroad in Venice, where I spent four months living above the best pastry shop in the city (fight me!) and learning about the art history of that magical place. The experience inspired me to seek dual-citizenship, a six-year process that acquainted me with the sheer absurdity of Italian bureaucracy, and yielded success in 2022.

But I still didn’t pick up and move. I always managed to convince myself it was impractical, or somehow not the right time. And this moment, mere months before starting a three-year graduate program in Boston, was not exactly ideal timing, to be sure.

And yet. On one of the last days in June, I scheduled a call with a decision coach, hoping to finally get certainty on this vexing dilemma of mine: To move to Italy, or not? On some level, I think I had already made up my mind and was simply seeking permission. Sure enough, we both arrived at the logical conclusion that yes, absolutely, I should move to Italy.

With two months left on my Boston lease, I set about making it happen. That very day, I took two life-altering actions that I could not easily reverse: I emailed my landlord to tell him I wasn’t renewing, and emailed the college to withdraw from my graduate program.

I eagerly texted my friends to give them the news: I was really, finally doing it. I was moving to Italy!

First things first: I made a checklist, which spawned many sub-checklists. I started ticking things off, as I am known to do.

In the weeks after that, I alternated between a feeling of ease (Ah yes, things are moving right along, this feels correct) and a feeling of overwhelm (OMG, how the f*ck am I going to pull this off!?) Moving to Italy is all fun and games until you get into the specifics, the logistics, the devilish details.

I started to doubt myself: What if I don’t find an apartment before the Italians take off for the whole month of August? Will I be able to enroll in the Italian health care system? What if I get there and feel utterly alone, unable to make any friends? (And why am I abandoning the ones I already have in the U.S.?)

Worries upon worries.

This move, more than anything, would require so much action in the face of these fears. So much tolerance for risk and uncertainty. In other words: Leaps upon leaps of faith.

I had to give up my beautiful Boston apartment without any guarantee that I’d have a new place to live come September. Once I did find an Italian apartment, I had to sign a multi-year lease for a flat that I had not seen in person. To secure said apartment, I had to wire thousands of dollars to foreign bank accounts, hoping it was not a scam.

Ragazzi, I am here now and I am thrilled to report: It was not a scam. Far from it. I arrived outside my building, four luggages in tow, and was soon greeted by the affable listing agent, who let me in.

After lugging my bags up four flights of stairs (no elevator 😅) I took in my surroundings. My new home was even better than I expected: An absolutely classic Italian apartment building, complete with a stone staircase and rooftop terrace. What a dream.

I write to you now from one of the many cafes in my lively new neighborhood. I spent my first day here wrangling with all manner of Italian bureaucracy (why wait???) and notching plenty of language successes and failures, before promptly collapsing and sleeping for 12 hours.

As for the rest of my week? I’ll be getting Wi-Fi installed, haranguing my landlord to fix my (currently non-functioning) fridge, and exploring the city a bit more.

High on my list for some exploration is a little place called Depot, a cruising bar that I’ve been itching to visit for, oh, I don’t know, the better part of a decade. I learned about it during my first visit to Milan in 2016 with my study abroad crew, but being a just-out-of-the-closet baby gay, did not have anywhere near the courage to visit a place like Depot.

Now? Well, I did move to the gay metropolis of Italy for a reason.

🤌🏻 Today’s Finocchio Fav

In each edition of this newsletter, I’ll try to give one recommendation for somewhere to eat or visit in Milan.

🍝 Dongiò — This lovely restaurant did not disappoint for my first Milanese dinner as a resident. Expect delicious, fresh pasta and a relaxed vibe.

P.S. If you’re here as a subscriber from a previous iteration of this newsletter: Hi! This space has become something completely new. Finocchio is my new publication about my queer life in Italy. I hope you’ll stick around, but if it’s not your cup of tea, no hard feelings.

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