Growing up with my Italian family in a Manhattan suburb, I always dreamed of visiting Italy.
While eating my grandmother’s famous spaghetti dinners and listening to her stories about what it’s like to explore the land our family came from, I longed for Italian experiences of my own.
My dream finally came true in October 2022, when I spent six days exploring Venice, Rome, and Milan for the first time while backpacking through Europe.
Four years later, I’m still thinking about six highlights that made the long-awaited trip everything I hoped for and more.
I remember taking in the Italian countryside from trains between cities.
I visited Italy during a two-week train trip through Europe. I took an overnight train from Vienna to Venice. Then I traveled by train to Rome and Milan. I spent two days exploring each city.
The passing landscape looked like something straight out of my dreams, with miles of grapevines and rolling hills behind them.
I’ll never forget the moment I saw Venice myself for the first time.
My first stop in Italy was Venice. I’d heard of the ancient city’s canals and car-free streets, but I didn’t expect to feel like I’d entered a storybook upon arrival.
It didn’t matter how many photos I’d seen of the over 1,000-year-old city — standing above the canals dotted with gondolas and lined with vibrant buildings struck me with awe.
After wandering the streets, I took a gondola tour to see the city from a different perspective.
Being in a narrow canal allowed me to see homes up close. Seeing their foundations disappear in the water felt surreal.
I was surprised to find I could book a stay in a castle.
For my stay in Venice, I booked an Airbnb stay at Castello di Roncade, a castle and winery just outside the city.
While wandering the castle’s stunning grounds, I was entranced by perfectly placed plants, over 100-year-old trees, and weathered sculptures of Venetian soldiers.
From Venice, I traveled to Rome, where I stayed in the most unusual accommodation of my life — a livable art sculpture I found on Airbnb.
My host told me he built the livable sculpture on the roof of his villa from recycled materials such as car windows, scrap wood, and broken tile.
Before booking this Airbnb, I’d never heard of a sculpture home. It felt like sleeping in a giant art installation, with quirky design elements in every corner.
I’ll never forget how amazing it felt to wake up inside this Airbnb with sunlight pouring in thanks to all the windows. I wish I could start every day like that.
While exploring the city on foot, I stumbled upon street artists. Under the shade of a tree near the Roman Forum, I watched one paint a church across the street.
I was especially surprised to see someone painting such an elaborate piece on a street corner. Seeing him immersed in his own world among so many people was inspiring to me.
A few minutes later, I spotted another artist sculpting dogs from sand.
I thought this was a unique artistic medium and found it fascinating to watch.
The last stop of my trip was Milan. During an aimless walk around the city, I was shocked when I found myself in front of a massive brick castle.
It was Castello Sforzesco, a 15th-century castle built by Francesco Sforza, a duke of Milan who founded the Sforza dynasty, according to Britannica.
I thought the castle looked like it came straight out of a fairy tale.
And since I wasn’t expecting to find it in urban Milan, my chance encounter made for a special memory.
I don’t think I’ll ever forget my first trip to Italy thanks to these unique surprises.
And I can’t wait to go back.
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