For all its contrasting natural beauty, no trip to Italy would feel complete without visiting at least one of its renowned cities. And there are plenty, to the point that listing them all and extolling their virtues wouldn’t fit in a list far more exhaustive than this one.
Instead, we've decided to introduce you to five can't-miss Italian cities. Three are famous the world over, while two are lesser-known gems you'll hopefully be delighted to uncover.
Getting Ready for the Trip
Before setting off, make sure you’ve handled the basics — book your accommodation in advance, check if you need reservations for popular attractions, and keep some cash on hand since not every spot takes cards.
It’s also smart to download an offline map, pack comfortable shoes for all the walking you’ll do, and learn a few Italian phrases to help you get around more easily.
In addition, whatever city you decide to visit, you’ll want to ensure that you can conveniently book a flight and safely browse once you get there. The best VPNs for iPhone or Android work well with your mobile devices. They can hide your IP address, encrypt your connection, and protect it from harm, which is a great help.
Now that the essentials are down, let’s get started with the cities you need to visit during your Italy trip.
Rome
You'd be hard-pressed to find another city in the world that embodies the concept of living history as well as Italy's capital does. After all, where else do still functional monuments dating back 2,000+ years to the zenith of one of the world’s mightiest empires blend as seamlessly with the heights of Renaissance art and contemporary architecture?
You can't venture 20 feet in any direction without brushing up against a building, square, or cultural activity of exceptional significance. St. Peter's Square, where the Pope gives his addresses, the Colosseum, the Sistine Chapel, or the MAXXI museum of 21st-century art don't even come close to scratching the surface.
Trieste
You’ll seldom find Trieste on typical top 10 Italian cities lists. All the better, as you’ll avoid the largest crowds while getting to immerse yourself in its rich and underappreciated beauty. Trieste’s distinct location and tumultuous past are reflected in a mix of Italian and Austro-Hungarian influences that give it a unique charm.
The Piazza Unità d’Italia is the city’s iconic sea-facing square. It’s home to Trieste’s seat of government, not to mention some of the best hotels and iconic cafés. Daytrippers are spoiled for choice, too. They can either visit the majestic Grotta Gigante caves, embark on olive oil and wine-tasting tours, or take part in local regattas.
Florence
While moderately sized by Italian standards, Florence towers above all but Rome in its cultural significance. It’s the mecca of Renaissance art, both plain for all to see in the majesty of its cathedral and inside the halls of the Uffizi Gallery, where art lovers go to pay homage to the works of the Renaissance's grand masters.
Travelers interested in a more hands-on approach can witness craftspeople produce jewelry and leatherwork in the artisanal Oltrano district. Foodies may enrich their experience with authentic Tuscan cuisine, especially in the fall, when local wine and truffle festivals are in full swing.
Matera
Even in a country as steeped in history as Italy, smaller, out-of-the-way places like the city of Matera can still leave one surprised and awe-struck. It’s famed for the Sassi, cave dwellings carved out of the soft yet durable limestone dominating the area. Staying overnight, shopping, or worshipping in some of these one-of-a-kind edifices is quite the experience.
Even without the Sassi, the surrounding cliffs and buildings that look like they sprang up from the earth itself make Matera uniquely photogenic. Movie buffs may also be interested in Matera since it was featured in The Passion of the Christ. Meanwhile, foodies can enjoy sampling or learning how to prepare some of the hearty, vegetable and cheese-focused meals that Lucanian cuisine excels at.
Milan
The last stop on our whirlwind Italian cities tour is the perfect destination for anyone interested in experiencing Italy at its most modern. That’s not to say Milan’s cultural pedigree is suspect, as the world-famous Scala and Sforza Castle can attest to!
Milan is where visitors to Italy get their high fashion and high-end shopping fix. There’s history even there, as the Galleria Vittorio Emanuele II is among the world’s oldest covered shopping arcades. Once you and your credit card are all tuckered out, you can take in the modern skyline or grab an aperitif and snack before you venture into Milan's vibrant nightlife.
Milan is also a finance and tech hub, making it a haven for digital nomads. While coworking spaces and other amenities abound, you’ll still want to make uninterrupted connectivity a priority if you decide to settle in Milan or any other of our picks. An Italy eSIM is the most elegant solution since eSIMs use local networks for comprehensive coverage and offer reasonably-priced data plans that let you work or stay in touch even if safe Wi-Fi options aren’t available.
Breathtaking Cities in Italy You Need to Visit at Least Once