I'm in Italy more than I'm not in Italy. I've visited every Italian region, most of them at least twice, and spent ample time in many of the country's major cities.
One of the most common questions I'm asked is which cities are worth visiting, and which aren't. It can be hard to narrow down the country's hot spots, especially for first-time visitors.
Of course, when it comes to travel, there are different strokes for different folks — but in my opinion, some Italian cities are more unmissable than others.
Rome is iconic for a reason.
I have visited Rome dozens of times, and I still have to pinch myself when I walk around what I could easily believe is a movie set.
Rome is, in my opinion, timeless: a city that doesn't shift and shape with trends. It's nicknamed the Eternal City for a reason.
Although Rome's most famed landmarks are worth a visit — especially the Colosseum and the Pantheon — for a more local feel of Rome, head to neighborhoods like Monti, Pigneto, and Testaccio.
Make sure to try some classic Roman dishes like carciofi alla Romana, pasta alla gricia, and scrocchiarella, a thin, crispy pizza. Some of my favorite spots in the city for true Roman cuisine are Trattoria della Stampa, tucked around the corner from the Trevi Fountain, and Trattoria da Zacca ar 20, near Vatican City.
Perugia is a medieval hilltop oasis.
Umbria is a wildly overlooked region. I speak from personal experience: It was my 18th region visited out of Italy's 20.
Perugia, Umbria's capital, is perched high above the hills, and the city is surrounded by walls that date back to Etruscan times. Its dramatic landscape, paired with the city's old town, makes for a medieval fairytale-like setting.
Perugia is also home to the famed Baci Perugina chocolates. Chocolate is so profound here that one of Europe's largest chocolate festivals, EuroChocolate, is held in the city each year.
Palermo is a dreamy street-food city.
It's hard for me to narrow Sicily down to one specific city. I've found the island to be entirely different from mainland Italy: From its Arab and Viking history to the language, Sicily feels like its own country.
However, if you only have time for one Sicilian destination, it needs to be Palermo. The city has heart and soul, but there's also a real grit to it: On the same street, you'll see an intricate church that dates back to the 12th century, right near cool, graffiti-covered walls.
If nothing else, go to Palermo to try street food. Classic dishes like arancine and panelle can't be missed, but if you want to eat like the true Palermitani, try pani câ meusa (spleen sandwich) and stigghiola (skewered lamb or goat intestines).
Many people skip over Bari, but they shouldn't.
I see the same mistake made in Puglia over and over again: Many tourists head straight to the picturesque small towns, like Monopoli and Ostuni, and skip Bari completely.
Bari is the heart of Puglia, though, and deserves at least a day of your time. Roam around Bari Vecchia, the city's old town, made almost entirely of light limestone buildings.
There, you'll find Strada Arco Basso, or the "Street of Orecchiette," where you can catch sight of nonnas handrolling orecchiette.
Bari is also where the city meets the sea. I recommend taking a stroll along Lungomare di Bari, the longest promenade in the country.
Bolzano is a winter wonderland.
For a long while, the Italian Dolomites — though aesthetically beautiful — were not my favorite part of the country. It wasn't until I visited Italy's largest Christmas market last December, held in Bolzano, that I finally fell in love.
Bolzano, known as the Gateway to the Italian Dolomites, is one of the coolest cultural cities I've personally been to. Bolzano is located in a part of Italy that was under the Austro-Hungarian Empire until 1918, and those effects are still felt today.
German is widely spoken here, and seeing knödel or spaetzle on menus is quite common. If you enjoy wine, the white wines of Alto Adige are recognized as some of the world's best.
Pro tip: While you're here, head to the South Tyrol Archaeological Museum to see Ötzi, a mummy that was found by a German couple hiking in the area in 1991.
On the other hand, Milan isn't exactly my favorite city.
Milan is the fashion capital of Italy and home to incredible artwork, like Leonardo da Vinci's "The Last Supper."
However, I've found that compared to other Italian cities, Milan has a more rushed, fast-paced feel that I associate with places like Paris and New York. It's also consistently ranked as one of the most expensive cities in the country, making it a pricey trip.
Don't get me wrong: The Duomo di Milano is one of the most stunning pieces of architecture in Italy, and proper Lombardian restaurants like Osteria Conchetta provide memorable meals.
Instead of planning a trip to Milan, though, I would choose a spot outside the city, like Brescia, to get a feel for Lombardy — and, from there, simply visit Milan on a day trip.
I find Positano to be overcrowded, overpriced, and overhyped.
I will say with my whole chest that Positano is not worth the hype. Perhaps those are fighting words, but despite its beauty, I often find Positano unbearably crowded, and the sweltering southern Italian heat doesn't help the experience.
That said, the Amalfi Coast is still worth a visit. I would, instead, recommend staying in Salerno.
Located on the edge of the Amalfi Coast, this city offers a more secluded and affordable escape. Plus, you will still be close enough to Positano, should you need to scratch the itch.
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Kaitlyn Rosati is an avid solo traveler, having visited all seven world wonders, all seven continents, and over 80 countries alone. Her passion for traveling the world began when she was a bartender in NYC, where she took long weekends to explore remote corners of the globe.In 2019, she quit her job, sold all of her belongings, and left New York for a one-way ticket to Tahiti to embark on a proper round-the-world backpacking trip. While on the road, she started to gain a following on her blog, No Man Nomad, and is now a full-time travel writer and content creator. Some of Kaitlyn's favorite destinations are Italy, New Zealand, Vietnam, and Tanzania, but that list is only bound to keep growing.
