Whenever I board a plane, I cross my fingers and make a wish at takeoff. I know, it’s a little quirky. I think I inherited this from my mom, who got it from her mom, all in the name of preventing a plane crash. Apparently, crossing your fingers is the secret weapon against disaster. So now, instead of just hoping the plane stays airborne, I’ve turned it into a full-blown wish-making ceremony. I’ll sit there, wedged between a crying baby and someone whose idea of personal space is a vague suggestion, thinking, “Dear universe, please grant me the ability to disassociate from this situation and land in a world where all my wildest ambitions come true. And please, please, please, do what you can to keep me alive today. I’ve got some plans that require my presence”.
Last year, as our plane lifted its wheels for a girls' trip to Spain and Italy, I wished for the greatest adventure of my life.
Let’s rewind to 24 hours before departure. My two best friends and I were huddled around my laptop on the living room floor of my New York City apartment, brimming with the kind of excited anticipation that only a trip to Europe can inspire. I was the first to discover that our flight to Barcelona had been canceled. My heart leapt into my throat. How had we not been notified? What were our options? Our flight hadn’t been rebooked, and there was no customer service chat online. So we did what every average American dreads: we dialed the customer service number and waited. And waited. And waited. And waited, eventually falling asleep with the phone on speaker. After about three hours, someone finally picked up, rebooked our flight, and broke the news that our return flight had also been canceled. Post-COVID flight cancellations had become the norm, but not being informed was a new level of shit show.
At 3 AM, with an early departure staring us in the face, I have no idea how we managed to get to the airport. The plane was so empty that I commandeered an entire row of four seats, stretched out horizontally, and enjoyed eight hours of uninterrupted sleep. With my eye mask, fuzzy socks, and airplane pillow, I was living my best life, more comfortable than any first-class passenger could dream of. That flight remains my all-time favorite.
In Barcelona, we danced through the streets, sipped on sangria, and devoured paella and patatas bravas. I watched my friends attract admirers from all over the world, score free drinks, and then we’d all stumble back to our hostel, holding hands like a pack of tipsy wolves. Traveling as a trio of single women was a magical experience—one of those vacations that makes you realize how lucky you are to be exactly where you are.
For the second half of our adventure, we flew to Florence. It came down to a choice between the South of France and Florence—two places that scream, I want to look cultured but also eat myself into a carb coma. Eight years ago, I had strolled the streets of Florence with my family, doe-eyed and naive, declaring it my favorite city. What did I know back then? I was an 18-year-old who’d only sipped wine at stuffy Sunday mass and was roaming those streets without even carrying a wallet. Yet, something about Florence stuck with me. Barcelona was already on our itinerary, and while I was pumped to revisit it with my girls—having once traipsed through it with an ex—I wanted new memories, ones to write over the ones that were no longer of service to me.
But Florence… it was calling. Was it the promise of gelato so good it could make you forget about every breakup? The cobblestone streets that were a chiropractor’s dream? Or was it something deeper, something that made me feel like I was chasing a part of myself I hadn’t found yet? I didn’t know what I was looking for, but I knew I had to go back. And, miraculously, my friends were on board, too. I may have been shelling out a small fortune for this trip, but I was about to live out my European fantasy, damn it.
We landed in Florence like we owned the place—minus the part where I had zero Italian under my belt beyond “Ciao,” which, let’s be real, I was overconfident in my delivery. As we hopped into a cab at the airport, I fumbled through Google Translate like my life depended on it. Let’s just say, when you’re trying to explain directions to a driver who looks like he’s witnessed a thousand clueless tourists before you, a language barrier feels less charming and more like public humiliation. There I was, the classic American tourist who hadn’t even bothered to learn how to say, “Please don’t overcharge me,” in Italian. Lesson learned.
Since we were fully embracing our post-college, broke-but-still-dreaming lifestyle, we booked a hostel. A solid $25 a night—just enough of a financial dive to make it feel like an adventure. So when the front desk upgraded us to a private suite (because apparently post-pandemic Florence was on vacation too), we reacted like we’d just landed front-row seats at the Met Gala. Honestly, the vibe was pretty much the same. Fancy enough to stroke our egos, but still gloriously cheap. It was peak bougie-backpacker—a combination that, let’s be real, suited us perfectly.
The crowning jewel of our accommodations? The bathroom balcony. Yes, you read that right. Imagine this: you shimmy out of a tiny bathroom window, climb a wobbly metal staircase that feels one bolt away from collapsing, and boom—you’re on the roof, overlooking all of Florence. Equal parts glamorous and ridiculous. It was like the universe decided, "Sure, you’re on a budget, but here’s a view fit for a king—just take the scenic route through your toilet”.
Every morning in Florence, I rose like a phoenix from the ashes of last night’s wine, slapped on my running shoes, and ran the entire city. I wasn’t just running; I was marathon training—very serious shit—but now with the soundtrack of The Light in the Piazza and The Lizzie McGuire Movie blasting in my headphones, because if I wasn’t channeling my inner Hilary Duff, was I even in Italy? Forget the marathon; I was manifesting my moment. I pictured myself on the back of some Italian guy’s Vespa, wind whipping through my hair, living a TikTok-worthy life.
And let’s be clear—I wasn’t just running through Florence, I was conquering it. Hangover? Minimal sleep? Nothing stopped me. Every run was a battle cry, a declaration of independence from my life back home, and while I was at it—every stupid life decision I had ever made. And also, it was strategic: I got the city to myself before the hordes of tourists descended, before selfie sticks cluttered the streets like a terrible plague. I had Florence in its purest form—silent, beautiful, and mine for the taking.
Each run felt like a prayer, though if I’m being honest, I wasn’t entirely sure what I was praying for. Was it a ride on the back of a sexy Italian’s Vespa? Uh, yes. That was very much at the top of the list. But there was something more. Deep down, I had the overwhelming sense that this trip was going to mean something. Not just in the I went to Europe and took a bunch of great Instagram photos kind of way, but in the I’m searching for something I haven’t quite found yet way. You know, the stuff they make whole novels out of.
Florence wasn’t just a place for me to eat my weight in pasta and pretend I wasn’t low-key falling apart—it was the place where I started to realize that maybe, just maybe, I was on the verge of something bigger than myself. Something life-changing. Or maybe I was just a little drunk on red wine and sunburned from the Italian summer. Hard to say.
It took a few days—and a solid amount of €3 wine—before we even considered climbing through the bathroom window to explore the so-called "rooftop." And I say "considered" because really, who decides to climb through a bathroom window on a whim? But this was Florence, and in Florence, you do things you wouldn't normally do. Like eat three gelatos in one afternoon or casually contemplate breaking an international law for the sake of a view. But we hadn’t quite reached the bathroom window level of reckless yet. No, we were still too busy being enchanted by Florence itself—David's marble ass was, of course, a highlight—and wandering the cobblestone streets with the kind of giddiness only a group of American tourists with no responsibilities could muster.
Still, the window lingered in the back of our minds like a dare waiting to be accepted. After all, what was the point of staying in a hostel with rooftop access if you never made it up there? It felt like a metaphor for life: You could see the opportunity right there, within reach, but you had to do something wildly uncomfortable to get to it. A bathroom window—the perfect metaphor for everything terrifying and exhilarating that stood between me and the version of myself I hadn’t met yet.
Then came the night after our return from Cinque Terre, sun-kissed and buzzing with that euphoric travel fatigue. That was when my friends decided it was time to go for it, and out they went, one by one, clambering through the window like they had done it a thousand times before. I sat on the edge of my bed, paralyzed, watching as they disappeared out of sight. I knew I should follow them, but anxiety, my constant companion, held me back. Because this was a big thing for me. Maybe it seemed simple on the outside, a small act of recklessness. But this was not just climbing out a window. It was about choosing to say yes to something that scared the hell out of me.
I sat there for a good twenty minutes, my brain ping-ponging between just do it and you're going to fall to your death and they’ll have to ship your body back home in a wooden box. My feet refused to move. But then I thought about everything that had led me here—to this city, to this trip, to this moment in my life. I had spent so long playing it safe, so long saying no to things that felt uncertain. Maybe it was time to stop clinging to certainty. Maybe it was time to take the leap—literally and metaphorically.
So, I did what I never did. I stood up and moved toward the window.
The climb was awkward and a little bit embarrassing, to be honest. I didn’t gracefully slip through the window like some cinematic heroine in a foreign film. No, I scrambled. Limbs everywhere, legs too long for the tiny opening, nearly knocking myself out on my way out. But when I finally made it through, hands clutching the edge of the window frame, I felt it—the jolt of fear and exhilaration that only comes from doing something ridiculous. I was out in the open air, standing on that tiny rooftop, with Florence stretched out before me like a painting, the kind you stare at for hours because it’s just too good to look away.
The sun was setting in the distance, casting the city in a warm, golden light. The Duomo glowed in the soft twilight, and the rooftops around us looked like something out of a dream. It was one of those moments you freeze in your memory, the kind you hold onto because you know it means something, even if you can’t put it into words yet.
And then I saw them. Across the street, on another rooftop, a group of young Italian men, lounging around like they belonged there. And they probably did, but still—it felt like they were part of the story that was unfolding before me, like they had been placed there by the universe, just waiting for me to notice.
Now, a normal person would have ignored them. Or waved. Or quietly slipped back inside the window without making a scene. But I was not a normal person. Not anymore. So, before I could stop myself, before I could second-guess the audacity of what I was about to do, I leaned over the ledge and shouted at the top of my lungs, “Hi!”
Time froze for a second. It was one of those moments where the air feels charged with electricity, where you know something is about to happen, something that could change everything—or nothing at all. My friends whipped around, eyes wide, like they couldn’t believe what I had just done. Honestly, neither could I. But there it was. I had thrown my shout into the world like a wild, desperate prayer.
And then, it happened. One of the guys shouted back.
“Ciao!”
My heart jumped into my throat. It wasn’t just the fact that he answered—it was the way he answered. Like he had been waiting for me to notice him. Like this was all part of some cosmic plan, and I had just stumbled into it by being brave—or reckless—enough to shout into the void. His accent was thick, his English broken, but it didn’t matter. I understood him perfectly.
The exchange between us felt like magic, the kind of magic that makes you believe in fate, in signs, in all the things you laugh off when you're trying to be realistic about life. But in that moment, standing on a rooftop in Florence, with the sky turning from gold to deep purple, I didn’t want to be realistic. I wanted to believe that this was something more than a chance encounter. That it meant something.
I think we all knew what was coming next. There was no way we were getting off that rooftop without something happening. And sure enough, they invited us over to their rooftop for aperitivo—and how could we say no? We had just been handed our very own Italian rooftop fantasy on a platter. Except, you know, we were still three girls in a foreign country, and our self-preservation instincts kicked in just enough to politely decline the possibility of sex trafficking and life somewhere in a medieval dungeon in Europe.
But they asked again for the following night. And this time, we said yes. Because, honestly, how often do you get invited for rooftop drinks by a group of beautiful Italian men while standing in the middle of a sunset-soaked city? How often do you get the chance to turn a passing moment into a story worth telling?
One of them shouted his number across the roof—Michele, I learned, because he yelled it so loud that I half-expected the entire block below to start taking notes. Michele. I liked it. It had a certain flair, like a name that could sweep me off my feet while simultaneously reminding me that I was probably in way over my head. His English was a little, let's say, under construction. His friend had to correct almost every botched digit. The first thing I shamelessly asked? "Do you have a Vespa?" Apparently, it was in the shop.
Sure, buddy.
But by then, I was already in too deep to care.
As the sun dipped below the horizon, we climbed back through the window, my head spinning with what had just happened. I couldn’t stop smiling. I felt different. Lighter. Like I had stepped into a version of myself I’d been too afraid to meet before. The girl who climbed through windows and shouted across rooftops. The girl who said yes to the possibility of something amazing.
