Verona needs to fire their head of PR. Even I had not visited Verona until this past February (and I have visited a lot of random Italian cities). It was simply not on my radar. I had no idea it had the best preserved Roman amphitheater in the world, or was a UNESCO World Heritage Site. I was pleasantly surprised by the beauty and charm of Verona. It is also much bigger than I expected with so many things to do and see.
I have yet to find a vacation spot that I love more than the adorable seaside town of Positano. I find Positano infinitely more enjoyable and relaxing than its famous neighbor, Capri. I love renting my reasonably priced beach chair (with this view) and eating fresh strawberries while sipping little bottles of prosecco. When you tire of the beach, you can explore the adorable town and purchase custom-made sandals from local vendors. The best part about Positano is that it is centrally located and you can easily bus, ferry, or drive to explore the other nearby towns of the Amalfi Coast.
Like Verona, Padua is a very old, and very important, city overlooked by modern-day travelers. Padua calls itself the oldest city in northern Italy (claiming it was established by a Trojan prince) and has the second oldest university in Italy. Yet despite its age, Padua (or Padova) maintains a hip and young feel today thanks to the still vibrant student population. Art and history lovers can marvel at the early (or proto) Renaissance frescos throughout the city (Giotto's Scrovegni Chapel being the most famous), while less art focused wanderers can explore the medieval streets and marketplaces.
Milan is Italy's banking and industrial center as well as its cultural and artistic tastemaker. It is also arguably the most "modern" and global city in Italy. But not every thing in Milan is modern, although much of the city was rebuilt after massive bombings in WWII. There are still lots of important historical sites, like Da Vinici's Last Supper, the amazing Gothic cathedral (it looks like lace!), and the old castle complex. In addition to these sites, Milan has amazing shopping!
Italy in general is known for its amazing food, but I contend that the best Italian food is in Bologna. I mean they invented spaghetti Bolognese! Like Padua, Bologna is also home to an ancient university (the oldest in Europe, in fact) and remains a college town today. Thanks to this, the city is dotted with great cafes, bars, and unique boutique shopping. Bologna has had lots of nicknames over the centuries -- the learned one (because of the university), the fat one (because of the food), and the red one (because of the medieval red terra cotta that remains throughout the city). It also just a 30 minute train ride away from Florence!
Have I missed any of your favorite Italian cities? Please share what you think are the most underrated destinations in Italy!