Florence Piazza
Amalfi Coast,  Best Of Italy,  Inspiration,  Italy,  Northern Italy,  Puglia,  Rome,  Sicily,  Tuscany

Best Cities and Towns In Italy

This article may contain affiliate / compensated links. For full information, please see our disclaimer. 

Best Italian Towns and Cities to Visit

Because there are so very many splendid towns and cities to visit in Italy, it is important to prioritize seeing them. Otherwise, we are in danger of missing some of the best there is. 

Here is our criteria for rating which towns and cities are the best in Italy.

Building and Street Character

The town or city has an ensemble of buildings (not just one building!) that clearly exhibit charm, romance, human scale, lovability, authenticity, and quaint-ness. A town or city best does this when it contains and preserves most or all of its historic buildings. Such buildings tend to be richly ornamental. In our list of the best, when we list a town or city, we are only referring to the historic old town of that town or city. This is, in our opinion, a town or city that has done a good job of keeping its “old town” intact, rather than modernizing it. Newer parts of towns and cities are excluded, as they almost invariably lack the above-cited features.

Towns or cities that have had too many historic buildings replaced by more modern buildings lose points for us.

The streets in the best towns and cities are often cobblestone. Many of the buildings are monumental (great in importance, extent, or size). Stunning, grand statues tend to grace public squares and piazzas. Streets tend to be relatively narrow in width.

Degree of Festivity and Fun

The town or city is a place that feels festive or vibrant. It is a fun place to be. So fun, festive, and vibrant that it easily creates unforgettable experiences for visitors. Some cities will only exhibit this during an annual festival or event or time of year (such as the December winter holidays), rather than throughout the year.

Quality of Food and Wine

Some cities are exemplary in the quality of the food or wine (or both) provided.

Strikes a Balance Between Stunning Sites to See and Being a Real Place

Some places are stunning (such as the Roman Forum in Rome) but are sterile, unused “museum” places frozen in amber. There is no community life in such places. A town or city that is just a “museum” loses points for us. On the other hand, large numbers of tourists flock to certain towns and cities for the very reason that they contain many sites that ARE stunning. That is why all the tourists are there! We believe it is important to visit most of the stunning attractions even when most are inundated with tourists — particularly when the attraction is relatively intact from the time of its glory.

The Three Categories of Best Italian Cities

Based on the above, we assign Italian cities to one of three categories (they are not ranked within categories, but simply listed alphabetically). The “Best of the Best” are towns and cities you must visit before you die. They are life-changing, inspiring, and sure to put you in a good mood. The “Great” are towns and cities that are important to see – so good that they are worth visiting more than once. The “Very Good” towns and cities are worth your time to visit at least once.

The Best of the Best

  • Florence
  • Palermo
  • Rome
  • Siena
  • Syracuse/Ortigia (Siracusa)(especially the outdoor market and neighboring deli in the Old Town)
  • Venice


  • Bologna
  • Cinque Terre
  • Lecce
  • Lucca
  • Matera (2019 Cultural Capital of Europe)
  • Modica
  • Montepulciano
  • Orvieto
  • Ostuni
  • Perugia
  • San Gimignano
  • Taormina

Very Good

  • Alberobello
  • Amalfi
  • Assisi (overwhelmingly charming, romantic, and human-scaled)
  • Bari
  • Bisceglie
  • Bormio (mostly for skiing)
  • Catania (almost entirely because of the famous La Pescheria fish market)
  • Cisternino
  • Civita di Bagnoregio (a town without much life, but too stunning and cute to miss)
  • Cortona
  • Herculaneum
  • Locorotondo
  • Martina Franca
  • Monopoli (lovely historic neighborhood streets)
  • Montalcino
  • Naples (Napoli)
  • Otranto
  • Piazza Armerina
  • Polignano a Mare (lovely historic neighborhood streets and stunning cove/beach)
  • Pompei
  • Positano
  • Ragusa Ibla
  • Ravello
  • Ravenna
  • Sorrento
  • Trani

Click here to see a locator map for each city and town.

Travel Guides
Follow Our Footprints
Follow Our Footprints
Apart from our complete travel guide on this website, here are other reading materials we recommend checking out before your trip.