Italy, Vatican | how not to plan a trip—and still end up in Rome

What a novel, a bookstore promise, and an old friend in Milan had to do with it

📚 The Book and the Trees

When I was around 14, my aunt gave me a book from her collection as a Christmas gift. It turned out, however, that I had already read it earlier that year. Normally, I would’ve gone to the bookstore and picked out a different one—but since this book hadn’t been bought in the first place… well, that option was off the table.

She said, “No worries, we’ll go to a bookstore another day and choose a book together.” As expected, she kept her word. A few weeks later, she gifted me, well, a handful of books.

One of them, The Baron in the Trees, from Italo Calvino, had a simple, curious premise. It was set in modern-era Italy and followed a young baron who climbed a tree in protest—and vowed to live there permanently. I won’t spoil it, but yes, he sticks to the plan longer than you’d think.

At the time, I was convinced this was a massive plot hole. “How come?” I asked my aunt. “He’d have to come down eventually. Sure, maybe he eats fruits—but he’d have to jump to the next tree, and for that he’d have to touch the ground.”

She smiled and said, “If you go to Italy, you’ll see how the trees connect at the top and form a kind of web. Back in the day, there were trees everywhere—so the premise isn’t as wild as it sounds.”

It took me a long time to get to Italy. Way longer than she probably expected when she said that.

Rome—I now can “see” the baron going from tree to tree, endlessly

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🗺️ Italy Wasn’t in the Plan

In my mind, I could “always” go to Italy. Meaning, there are trips you should do when you’re young with no kids.

For example, gorilla trekking in Uganda might not be the best choice for a family trip. Or if you’re over 60, you’re possibly not fit enough to chase gorillas through the thick jungle (called Bwindi Impenetrable Forest, look it up). Or maybe you can, but I’m not sure how I’m going to age.

On the other hand, going to Italy is very plausible when you’re well into your 60s, 70s, or even 80s perhaps.

So, “naturally”, I never really thought about going to Italy or, at least, made it a priority.

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🌍 How Italy Made the Cut

Confession: Italy was never part of my original itinerary.

When I first began thinking about this journey—more as a backup plan for not moving to Europe—I imagined starting in Berlin, tracing the Cold War divide, then heading East: through Eastern Europe, the former USSR republics, China, Southeast Asia. Maybe Japan.

Then Marco, one of my closest friends from NYC, moved to Milan.

Six months later, the trip turned from an idea into a plan—and I figured I’d stop in Italy to see him.

That’s when I ran into a cousin in NYC who said, “What do you mean you’re going to Italy and not visiting us in Portugal?”

And that’s how, six weeks in, I still haven’t started my original route. So far: Portugal, Morocco, Spain, France, Monaco, Italy—and, yes, the Vatican. Seven countries and counting.

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🍝 A Weekend in Milan

I only spent a weekend in Milan. Just enough to catch up—not enough to see the city. And that was okay.

It was more of a “traveler” kind of stop than a “tourist” one. I had long meals with Marco and his friends, reconnected with Elene (a friend from Emory), and strolled through the Duomo di Milano area.

I caught the tail end of a marathon and was reminded of how much I admire runners. The discipline, the training, the endurance—especially those finishing under three hours, which is when I arrived at the finish line. It brought back memories of watching the NYC marathon in the fall, one of my favorite things to do in the city at that time of the year.

Milano—The finish and the Duomo

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🇮🇹 “You’re Not Going to Rome?!”

After Milan, I planned to head north—Innsbruck or Munich.

But when I told my Italian friends I wasn’t going to Rome, they looked almost offended. “What do you mean you’re not going to Rome?”, they said.

“No, no. You have to go to Rome.”, they interjected.

Okay, okay. I gave in.

Rome hadn’t appealed to me at first. It felt like the kind of city you can “always” go to. Plus, I’d head south to head north again, and I wanted to avoid zig-zagging across Europe.

On top, Rome is full of tourists. Crowds. People wandering a bit aimlessly. Tourist traps. Selfie sticks. Restaurants with pictures on the menu. Overpriced items. A café was charging €6 for a cup of coffee. I almost asked the waiter to walk me through their cost structure to land at that €6 for a simple pour. I walked out instead. Pickpockets. Shady guys talking about your shoes and trying to grab your hands, aggressively asking where you’re from.

But… I had time. And I do love history.

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🏛️ Three Days in the Eternal City

So I went. And I played full-on tourist in Rome. I shamelessly ate at the closest pizza place after spending a whole day walking through the Colosseum and the Roman Forum.

Roman Forum seen from the Palatine Hill

I also spent two days exploring the Vatican. It was like a throwback to my Catholic school education.

Fun fact: I went to the Saint Augustine School in Rio. At the Cathedra Petri in St. Peter’s Basilica, there’s a massive sculpture featuring Saint Augustine himself—along with Saints Ambrose, Athanasius, and John. Ahem, there was no Saint Benedict or Saint Ignatius. Just saying.

Saint Peter’s Basilica at dusk—an aura that is matched on the inside

To my surprise, the Vatican Museums also had a lot dedicated to the classical works of art, and it neatly tied together the two worlds, “pagan” and Christian.

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🚶‍♂️ Wandering Rome

Every day, I used the mornings and afternoons for sightseeing. Evenings were for wandering.

I loved how Rome blended layers of history—modern, classical, and ancient—all in one walkable canvas. You always feel that you just might turn a corner and see something completely unexpected. Or maybe just something very mundane and yet quite charming.

I definitely wasn’t expecting this motorcycle to come along, and if this is not the definition of “quite charming”, I’m not sure what it is

It was rushed. I saw a lot, but there’s still so much more to explore. And that’s okay.

I tossed a coin in the Fontana di Trevi.

So yes, I’ll be back.

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✉️ Enjoying the journey so far?

💬 Got thoughts, travel tips, or your own “accidental Italy” moment?
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