10 best medieval cities in Italy - Italy Best

10 Best Medieval Cities in Italy

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Walking through the streets of some Italian cities, you might have come across very specific ruins that seem to come straight from one of those history books we had at school. Mainly, you might have seen the walls that once surrounded medieval cities such as Rome or Siena. Italy has most certainly hosted one of the greatest explosions of art during the Middle Ages. We have imagined this guide to the 10 best medieval cities in Italy for your pleasure – discover the details of one of the most culturally rich countries in the world!

10 Beautiful Medieval Cities to Visit in Italy


As the country was divided into many little regions, each one of the cities was led by the main town of the province. They all fought to produce the most wonderful paintings and sculptures. Not only that, but they also built the biggest buildings, and wrote some of the most lyrical poems.

If you share our interest in Italian history, then you have come to the right place. Read on to find out which are the 10 best medieval cities in Italy – Welcome to History!

1. San Gimignano

Known internationally as a medieval Manhattan, San Gimignano proudly displays its high middle-age towers. Many of them were destroyed all through the country by wars and catastrophes. This town is a true gem for all the visitors seeking a time travel right into the Middle-age.

Discover all the sinuous streets of San Gimignano, and climb to its highest point to get the chance to admire the breathtaking Tuscan landscapes. The town also boasts amazing food scenery – do enjoy a glass of wine in its unique restaurants!

2. Siena 

10 best medieval cities in Italy - Italy Best - Siena

Step back in medieval Italy to one of the prettiest cities you will ever get to see. Appreciate the out-of-time architecture of its gothic cathedral, enriched with the masterpieces of Donatello or Michelangelo.

Maybe you’ll feel more at home in the greatness and singularity of its Piazza del Campo. Our favorite thing to do in Siena? Enjoy the panoramic view you can get by climbing up the Torre del Mangia. Make sure you check out the best hotels in Siena too!

3. Perugia

Get a full medieval experience in this must-visit Italian city. From its central square where reigns the Fontana Maggiore, walk under the typical arches and ancient stone walls.

Take the time to observe the outstanding details of the stunning Perugia. For as small as it is, this city remains an intact part of the Italian historic and artistic heritage. If you need accommodation in the town, make sure you check our Perugia hotels list!

4. Civita di Bagnoregio

Dive in a surreal and fairy atmosphere by visiting the “dying city”. The unique beauty of this city is beyond everything you would expect from a medieval city. Surrounded by the valley of Calanchy, its upland position could give you the impression that the city is suspended in the air during foggy days.

Since it is unserved by any type of transportation means, only your feet and your desire to discover this medieval village will take you there. The 300-meters suspension bridge is a sight. We think that with its distinctive look and richness in history and feeling, you might be on the verge to do the trip of a lifetime.

5. Stilo

10 best medieval cities in Italy - Italy Best - Stilo

Who wouldn’t want to visit this little village? Stile is one of the best medieval cities in Italy. Well, a town actually. Inscribed in the list of the most beautiful villages in Italy, it is mostly famous for its Cattolica di Stilo. And we understand why!

► Read: 10 Best Things To Do In Venice Italy

The building deserves its reputation for the way it constitutes, from the bottom of each stone, a real architectural jewel. Its color, its domes, and arches continue to watch over the village after 11 centuries. Do not hesitate on going up to the Cattolica to see the sun rising and igniting the little medieval houses. 

6. Ferrara

You may want to go to this city for many reasons. Its title of World Heritage Site is due to the fact that Ferrara has been one of the European capitals of culture, arts, and politics. For us, it is one of the very best medieval towns in Italy. Not only was it a reference point for artists and poets, but it also hosted many literary figures.

The Estense castle came to symbolize the power of one of the most important European dynasties and the greatness of the entire city.

Ferrara was already known for its culinary tradition back in the Middle Ages, mostly represented by the cappellacci di zuccapasta with the shape of a hat and a pumpkin filling. If you find yourself in this city, you will have the opportunity to go to the oldest wine bar in the world: Al Brindisi. 

7. Bologna

10 best medieval cities in Italy - Italy Best - Bologna

Bologna is probably one of the best medieval cities in Lombardy Italy. You will love its Museo Civico Medievale and the two medieval towers, which played a role in making Bologna famous. Walk along with the fortified gates of the cities and admire the urban medieval structure of a city laden with history.

Step in the first university of Europe -Alma Mater-, founded in the 11th century. Observe the complexity of the Basilica of San Francesco in Piazza Malpighi and Piazza San Domenico.  And after that, do not miss the occasion to eat in some of the best restaurants in Italy! 

8. Roccantica

Get ready to be charmed by the endless maze of staircases of Roccantica. Its grey stones and cobbles enclose hundreds of years of history. Plus, it is only an hour away from Rome!

Fall in love with the simplicity of Santa Caterina, a small and typical middle-aged church. If you can, do attend the medieval festival of the town in August – what an otherworldly sight! 

9. Pitigliano Alongside San Giminiano

Pitigliano is probably one of the best medieval towns in Tuscany Italy. It is very famous because of its many medieval structures. The Cathedral of Santi Pietro e Paolo, Pitigliano, the church of Santa Maria, or the Orsini Fortress are all landmarks of Pitigliano. The town is well worth the stop if you are still looking for some amazing medieval experiences.

If you are willing to go the extra mile, we hear that Bergamo is also one of the best medieval towns in Tuscany Italy – why not make a trip to both cities?

10. Verona 

10 best medieval cities in Italy - Italy Best - Verona

Famous for being the town that hosted the story of Romeo and Juliet, Verona actually displays its historical richness through the most stunning architecture. Amazing cathedrals, churches, piazzas, and castles are all in the game. It is one of the best medieval cities in Italy, with a vibe that will take you back to the Middle-Age.

Enjoy some of the best local dishes, and get lost in the streets of a city that proudly shows up as one of the best medieval towns in Italy.

Wrapping Up 10 Best Medieval Cities in Italy

There you have it – a list of the 10 best medieval cities in Italy, all laden with history, wars, architecture, and arts. We love to discover new medieval cities in Italy, and how could we not? There, you can be yourself, or someone else. You can discover the very best of the Italian culture, and lose yourself in century-old streets. If you are more of a beach type, why not check out the best summer holiday destinations in Italy? Thank us later!

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3 thoughts on “10 Best Medieval Cities in Italy

  1. I feel like you could spend one years to travel in Italy and you still wouldn’t see everything 😂

  2. I especially love Italy for this medieval cities, it’s such a massive resources of history!

  3. I very enjoy Verona, the charm of this city blows my mind, when I’m there I just feel so free

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