t all started with a canceled flight. The kind of hiccup that should’ve sent us spiraling, frantically searching for new routes, praying to the travel gods for mercy. But Italy, in all her unpredictable charm, had other plans. A rebooked nonstop flight landed us in Rome earlier than expected, as if she had been waiting for us all along. We stepped out into the golden morning, blinking into the light, the scent of warm cornetti, espresso, and something sweet curling through the streets. There was no agenda, just time—a city to get lost in.
Our Airbnb overlooked Trevi Fountain, a postcard brought to life, the sound of water trickling below a constant reminder of where we were. We stood there for a moment, barely speaking, just taking it in. Rome stretched out beneath us, a city that doesn’t rush for anyone, but also refuses to wait. So we let ourselves fall into its rhythm, half-exhausted, half-electrified, wandering through the streets, stopping wherever curiosity tugged. A tiny magic shop. A café where an old man read his newspaper like a ritual. A bakery with pastries dusted in sugar, melting on our tongues before we even made it back to the street.
We found ourselves at Barberini Corsini Gallerie, where gold-framed oil paintings stared back at us, silent and unmoving, untouched by time. The halls smelled of old books and marble dust, of stories we’d never know but could almost hear if we listened closely enough. We whispered without realizing it, sinking into the kind of stillness that only comes from standing in a place that has existed longer than your entire bloodline. Then, straight to dinner. Because in Italy, time moves in meals.
At Aroma, the Colosseum sat in front of us, glowing beneath the night sky, watching us the way it had watched over centuries of lovers, fighters, dreamers, and fools. Bread soaked in olive oil so rich it could’ve been bottled like perfume. Pasta that made us reconsider everything we thought we knew about food. Wine so smooth it melted the hours. The conversation stretched, dipping in and out of laughter, and for the first time since landing, we exhaled. The moment wrapped around us like a scene from a film, one we wished we could pause, rewind, relive.
The night wasn’t ready to let us go. At Court Rome Bar, we drank slowly, staring at the Colosseum as if it might disappear, as if we might disappear.
We saw Trevi Fountain the way it’s meant to be seen—before the world wakes up. The three of us, standing before the water, the city still stretching itself awake. A quiet moment in a place that never truly sleeps. Coins tossed, wishes made, a secret left behind in the ripples. And then, the Vatican. Skipping the endless lines, stepping into halls dripping in gold and history (shoutout Skip The Line Tour through Viator). The weight of it pressing into our skin, the Sistine Chapel looming above us, silent, sacred, impossibly vast.
By the time we reached All’Antico Vinaio, we had earned it. The kind of sandwich you eat with both hands, sauce dripping, a perfect mess of flavors. We carried them into Villa Borghese, sprawling onto the grass, letting the city breathe around us. And then—X Games.
Somehow, in the middle of Rome’s most serene garden, we found ourselves watching skaters launch themselves into the air. The unexpectedness of it, the absurdity of sitting in the heart of an ancient city, drinking bottled spritz while someone flipped a skateboard over concrete—it was perfect.
Sicily moved slower, like a sigh, like a dream slipping between your fingers. Our villa wrapped around us, quiet and sun-drenched, the kind of place that makes you forget the concept of time. We let stillness take over. Afternoons spent by the pool, the air thick with the scent of lemons, our only responsibility to keep our wine glasses from ever being empty. Then, Mt. Etna. The ground beneath us—charcoal-black, foreign, alive in a way that made the earth feel younger. The wind howling through the rocks, the sky stretching endlessly above. And the wine—born from the mountain itself, earthy and deep, like drinking fire turned into fruit. Cannot forget about the honey. All that honey especially the pistachio! A final beach day in Taormina, the water kissing our sun-warmed skin, a silent farewell to an island that had already settled somewhere inside us.
Positano was love at first sight. A town that shouldn’t exist the way it does—stacked against the cliffs, spilling down toward the sea like a daydream. The air tasted like salt and citrus, like something stolen from a fairytale. At Da Adolfo, the storm teased us from the moment we sat down. Rain threatening, but never falling—until it did.
And then—hail.
It crashed against the umbrellas, against our shoulders, against our wine glasses. But no one left. Instead, we did what Italians do best—we stayed, we ate, we drank, we laughed harder because of it. The storm became part of the story, the meal richer because of the downpour. And when it finally passed, we had made friends in the rain.
That night, we stepped into Don’t Worry Bar, inside Le Sirenuse. Elegant, refined, poised—until Whitney Houston came on.
And then, we started the party.
At first, they hesitated. And then, one by one, they joined. The entire bar—dancing, singing, raising glasses, laughing like we had known each other forever. The kind of night you don’t plan, but wouldn’t change a single second of.
The morning came with a slight hangover and a boat to Capri. The sun fierce, the sea glittering, the air sharp and salty.
From Naples, the train rocked us into Florence, the countryside rolling past in endless golds and greens. The pace of the trip shifting, softening. Florence gave us Camila.
A woman who welcomed us into her farmhouse as if we belonged there. We kneaded pasta from scratch, sipped wine they made themselves, dipped thick bread into olive oil so pure it could’ve been a meal in itself. The meal stretched into the afternoon, unhurried, unrushed, the way good meals should be.
From Florentine Steaks at the best Trattoria Dall’Oste to Belle Donne wine window making friends. That night—a rooftop record bar, espresso martinis in hand, the Duomo glowing below. What a favorite city it became.
Then came Lake Como, where time seemed to stand still in the most beautiful way. Villa D’Este cradled us in luxury—boat rides on the Lake passing by neighbors like Clooney, immaculate spas, poolside spritz, candlelit jazz spilling into the night. The grounds itself is something beyond compare.
And then, the road trip to the Dolomites.
The drive wound through mountains, the air cooler, crisper. At one point, we passed a whole herd of sheep grazing right next to us, an unexpected, perfect interruption. By the time we reached Alpine Retreat Ruffrè, the sun was setting, casting long shadows over the mountains. That night, we curled up with blankets and a bottle of wine for movie night in the retreat, watching the mountains turn black against the deep blue of the sky.
The next day was hiking through Bolzano and Mendola, trails leading to views that stretched for miles. It felt like a deep breath, like the kind of quiet you don’t realize you need until you have it.
And then, Venice.
A city that shouldn’t exist, but somehow does.
We lost a phone in Burano, found it miraculously charging in a café by the staff, waiting for us like it had never left. Couldn’t even go into it more you had to be there. Then, mosquitoes on the ferry back. A crime. A personal attack really. It was insane.
But Venice redeemed herself with the best pizza of the trip—so good, we went back twice.
Over Two weeks.
A thousand stories.
Italy, you win. Again.
