August 27, 2025 – Page 22 – Advertising and Donations

Boats parked in a canal between rows of buildings in Venice, Italy — Business Insider’s reporter visited Venice, Rome, and Milan during her first trip to Italy.

Joey Hadden/Business Insider

Italy is a European country I’d always dreamed of visiting. In 2022, that dream came true.
I spent six days exploring Venice, Rome, and Milan. Each destination surprised me.
From castles and train windows to an art sculpture Airbnb, these were the biggest shocks of my trip.

Growing up with my half-Italian family in a Manhattan suburb, I always dreamed of visiting Italy.

While eating my grandmother’s famous spaghetti and meatball 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 — at age 26 — spent six days exploring Venice, Rome, and Milan for the first time while backpacking through Europe.

Nearly three years after my Italian adventure, I’m still thinking about six surprises that made the long-awaited trip everything I hoped it would be.

While taking trains between cities, I remember looking out the windows and being stunned by the Italian countryside.

Business-class seating on a train from Venice to Rome.

Joey Hadden/Business Insider

I visited Italy during a two-week train trip through Europe. I took an overnight train from Vienna to Venice to get there.

Then I traveled by train to Rome and Milan. I spent two days exploring each city.

The rolling hills were one of the most picturesque views I’d ever seen from a train. The scene looked like something straight out of my dreams.

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.

A view of Venice from a gondola.

Joey Hadden/Business Insider

I’ll never forget the moment I saw Venice myself for the first time. 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 of Venice, I took a gondola tour to see the city from a different perspective.

Being in a narrow canal allowed me to see homes from inches away, and the moment I spotted their foundations immersed in the water felt surreal.

When researching accommodations for my trip to Venice, I was surprised to find I could book a stay in a castle.

The grounds of Castello de Roncade outside of Venice, Italy.

Joey Hadden/Business Insider

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.

The author stands on a colorful patio in front of the sculpture home — Joey Hadden/Business Insider

My host told me he built the livable sculpture on the roof of his villa using recycled materials like car windows, scrap wood, and pieces of broken tiles.

Before booking this Airbnb, I’d never heard of a sculpture home. I imagined it would feel like sleeping in a giant piece of art, with quirky design elements in every corner. Turns out, I was right.

Inside the livable art sculpture.

Joey Hadden/Business Insider

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 was surprised by alluring street artists. Under the shade of a tree near the Roman Forum, I watched one paint a church across the street.

A man in Rome paints the 15th-century catholic chapel in front of him — Santa Maria di Loreto.

Joey Hadden/Business Insider

Seeing him immersed in his own world among so many people was remarkable and inspiring to me.

A few minutes later, I spotted another artist sculpting dogs from sand.

A artist sculpts dogs from sand on the streets of Rome.

Joey Hadden/Business Insider

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 to stumble upon a massive brick castle.

The entrance gates of Castello Sforzesco in Milan.

Joey Hadden/Business Insider

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.

A composite image of the author standing and taking a photo on a cobblestone street in Rome — The author photographs a cobblestone street in Rome.

Joey Hadden/Business Insider

And I can’t wait to go back.

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