My Favorite City in Italy

This is the most common question I am asked as an Italian Travel Planner. Here is why and how I chose 'the one.'


It was the 26th sunset I watched from my little local bar this summer.

While my nonni were from Sicily and I spent 10 years living between Florence and Tuscany, life somehow brought me here to Sorrento.

I can’t describe the way the sun glows over the Tyrrhenian Sea from this town. It’s like a painting. To the right I see Mt. Vesuvius peaking her head out, to the slight left I see the volcanic island of Ischia gleaming next to the sun as it slowly fades. On the far left, I witness the cliffs take the last ray of light, proving this Southern touristic city truly sparkles from land to sea.

Being surrounded by two active volcanoes never seemed to phase me. My friends in New York thought it was strange, especially when I tried to explain that it was Vesuvius, which brought me comfort while traveling.


It always gave me that feeling of ‘welcome home’ when I arrived in Campania, a feeling just a few understood. The few I am referring too were usually locals of the area. I confirmed this theory two weeks prior to this sunset. I was driving to the office in Naples when Gabriella, a Napolitana colleague put into words, this unexplainable feeling to me.


“She’s beautiful, isn’t she,” said Gabriella as the sun rose leaving the sky in a bright pink. “Chi?” I responded. “Vesuvio,“ she said.

“Si, Si “ She nods her head in self-agreement to my response. “Hey, Gabriella, did you have any fear of living so close to this volcano anytime in your life?" I asked. A quick look flashed my way, “ma daiii, FEAR, ha, she is our protector, and a gift that we very much treasure here in this land.“


Ho capito” I said. She didn’t have to say much for the rest of the car ride, as I strangely understood completely.

As my mind brings me back to the current moment, the sun has gone down and now I decide to go up to my apartment. I wave to the local baristas who serve me daily, starting from my caffe macchiato and fresh cornetto with amarena and crema to my evening aperitivo. They give me a wave and a smile but I know, just as many others in town they are wondering the mystery behind this Italian American single girl living upstairs from the bar (yes me).

As I walk up the steps, I am welcomed by the zia of the family building I live in. She has a Bialetti with fresh espresso in hand, and was waiting for me to arrive. “Cassandra
(or Alexandra as she called me for the first month) caffé?” Her face holds that questionable gesture whether I would come into her home or would I like it to go. Of course I took advantage of taking the coffee in her apartment. Besides being able to practice my Italian, she was delightful company and she had a splendid view of the beloved sea and coast that I could not get enough of seeing.

From her window I spotted our local beach, the umbrellas being closed, the families packing up. I guess calling it a beach is a bit of an overstatement. Here in Sorrento we have decks and patches of sand surrounded by beautiful rock formations. So maybe it’s not exactly a white sand beach but for us locals, it was basically a private swimming pool with natural salt water, so no complaints.



As the sky turns into golden stars, I find myself wondering how the heck I got to this beautiful place, how could I be so lucky?


However, when I glance back over at Mt. Vesuvius, I strangely felt a bit of sadness arise.

From her window, I can also see the twinkling lights of Naples in the distance. What is it with me and this city? Here I am in the middle of a paradise and I am dreaming of being in the ‘wild child’ of Naples?

I had just spent a little under a month there. My business colleagues and I planned it this way, as they wanted to show me the ‘MOST BEAUTIFUL CITY IN THE WORLD.’

They not only wanted me to bring my clients to the city with confidence but also they were hoping I would spread the news of Naples beauty during my travels throughout Italy.

Naples has always had an interesting reputation and I am convinced that my Neapolitan friends believe their mission in life is to break this false perception and show the world what city truly has to offer.

They would talk about this so much that there were times I stopped listening. As a travel planner, I LIVE off of hearing and seeing a local Italian's point of viewpoint while traveling. However, in this case they would not let down without convincing me to say that I fully agreed that Naples was indeed the most beautiful city on earth.

Well it was this moment as I gazed at the city from Sorrento, did I feel their same love, passion, and pull that my friends were trying to express to me so adamantly during that time.


While in Naples, they set me up in one of their family apartment rentals. With the apartment being beautiful, centrally located, and having a pink refrigerator, I was happy. It also had a splendid view all around me. Some of the highlights of this view were of the sea, the daily fireworks (for honoring the saints of course), and my neighbor watching TV on his rooftop every night after 8pm.


I have traveled the city quite a bit prior to this stay, as my ex fiancé was from there and I was a former tour leader for the region. However, I had a different outlook now, one full of appreciation from my tour guides and friends. Their enthusiasm and passion were real, and anyone or anything with passion always has the ability to make an impact on my life.

While in Naples, I found myself out daily exploring the streets, even without my guides. I had the looks of a tourist, always in awe of what I saw, but heart of a local. Crocchè di patate, fried pizza, and sfogliatella, it was ever-savory bite that made it more impossible to leave.

Even the people always surprised me. From the barista who knew me as the “New Yorkese," the cheese man at the local shop up the road (who knew me as the woman he spoke to about the sadness of his recent divorce), the hipster café waitress who referred to me as the girl that fought with her colleagues to pay during work outings, to the restaurant owner that gave me free sushi, simply because I was by myself. I once saw myself as a stranieri desperately trying to fit in but as I left the city, I realized many simply saw me as another person who gave their Napoli a chance and because of that I have left an impact on them.

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As someone who lives in NYC half the year, it’s the liveliness of Naples that intrigues me. It’s the secrets I want to understand about this city. It’s mysterious place that easily opens their heart and soul to you once you finally get to know it but first approaches you with caution and approval. It’s the mystery that I hold in my own life that feels one with this so-called ‘wild child.’

When I finally come back to reality, I realize zia is staring at me, obviously waiting for a response. “Cara, tutto ok?” “Si signoria, scusata,” I reply.

“I asked what is your favorite city," she explained, “for someone who said they have traveled 12 regions this year, which is more than I have seen in my lifetime as an Italian, tell me which has the most beauty? Sorrento, vero (with a wink).”

When asked by an Italian a question such as this one pertaining to their city, any other normal person would of said si certo (yes, of course) but not me. I have a habit of doing this, being a little too open with my feelings and thoughts.

 My Italian friends say this is because  I am “persona per buona” (a person for the good) who tells the truth and maybe a little too much according to them.

I take a breath and shoot her a smile.“Yes Madame, Sorrento is one of the most breathtaking places on earth and I love all the people here in this town. I also love the café culture in Torino, the Sassi of Matera, the white washed buildings of Puglia, the seas of Liguria, the view of Bellagio on Lake Como, the way the sun reflects off the Arno in Florence, and the rolling hills of Tuscany all the same. “


Signoria, I think I would describe it like this, Sicily is my family, Florence was my savor, Sorrento/Amalfi Coast is my dream come to life, but Naples is my soul.”

“So it's Naples I chose as my favorite. This is not because I have spent a lifetime there and know it oh so well, it is because I still have so much to learn. It’s because it’s the city that will keep me coming back time after time until I figure it out and make it fully part of me and my half Italian life.”

“Brava, Cassandra then it's Napoli that shall most lovingly open its heart to you, now drink your caffe before it gets cold.”


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Cassandra Santoro is the CEO and Founder of Travel Italian Style. As a personal trip planner, Cassandra is an expert in Italian travel with a focus on authentic and inspiring experiences.

She also leads motivational talks and can most recently be found at TEDx DHBW Mannheim.

Cassandra currently lives between Brooklyn, NY & Italy. Follow her adventures of life between two countries on Instagram.