Ten Best Medieval Cities of Italy

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You might have seen ruins in some Italian cities as you walked through them. You might have seen walls that once surrounded medieval towns like Rome and Siena. It has certainly seen one of the most significant explosions in art during the Middle Ages. This guide will show you the top 10 most beautiful medieval cities in Italy.

Italy’s 10 Most Beautiful Medieval Cities


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Each city was led by the principal town of the province, as the country was divided into smaller regions. They all worked together to create the best sculptures and paintings. They not only created the best paintings and sculptures, but also wrote the most poetic poems.

You are welcome to join our passion for Italian history. Continue reading to discover the best 10 medieval cities of Italy. Welcome to History!

1. San Gimignano

San Gimignano is internationally known as a medieval Manhattan. It proudly displays its high-class middle-aged towers. Many of these towers were destroyed by wars or natural disasters throughout the country. This is the perfect place for anyone who wants to travel back in time into Middle-age.

Explore all the streets of San Gimignano and climb up to the highest point to see the stunning Tuscan landscapes. You can also enjoy amazing food scenes in the town.

2. Siena

Take a step back in medieval Italy and visit one of the most beautiful cities that you’ll ever see. Admire the unique architecture of the cathedral’s Gothic style, which is enriched by the works of Donatello and Michelangelo.

Perhaps you will feel more at home in its Piazza del Campo’s singularity and grandeur. What is our favorite thing to do while in Siena You can enjoy the breathtaking view from the Torre del Mangia.

3. Perugia

This must-see Italian city offers a complete medieval experience. Walk under the traditional arches and stone walls from the central square, where the Fontana maggiore reigns.

You should take the time to admire the amazing details of Perugia. Despite being small, the city is still a significant part of the Italian artistic and historic heritage.

4. Civita di Bagnoregio

Visit the “dying town” to experience a surreal, fairytale atmosphere. This city’s unique beauty is unlike anything you might expect from a medieval town. It is surrounded by Calanchy’s valley, giving it the appearance of suspended in the air on foggy days.

It is not accessible by any transportation method. You will need to walk there and explore the medieval village. It is worth a visit to see the suspension bridge that spans 300 meters. With its unique look, richness in history, and feeling, we think you may be close to making the trip of your dreams.

5. Stilo

This little village is a must-see. Stile is one the most beautiful medieval cities in Italy. Actually, it’s a town. It is a listed in the top ten most beautiful villages of Italy. Most famous for its Cattolica di Stilo. We understand why!

Read: The 10 Best Things to Do in Venice Italy

It is a true architectural gem, and the building deserves it. After 11 centuries, the building’s color, domes and arches still watch over the village. Don’t hesitate to climb up to the Cattolica and see the sun rise, igniting the small medieval houses.

6. Ferrara

This city may appeal to you for many reasons. Ferrara is Europe’s capital of culture, art, and politics, which has earned it the title of World Heritage Site. It is considered one of the most beautiful medieval towns in Italy. It was a point of reference for poets and artists, but also hosted many literary personalities.

The Estense castle was built to represent the power and greatness of one of Europe’s most important dynasties, as well as the city itself.

Ferrara was known for its culinary traditions back in the Middle Ages. This is mainly represented by cappellacci di Zucca, a pasta that has a pumpkin filling and is shaped like a hat. You can visit Al Brindisi, the oldest wine bar anywhere in the world, if you’re lucky enough to be in this area.

7. Bologna

Bologna is a great medieval city in Lombardy Italy. Bologna’s Museo Civico Medievale, and its two medieval towers will be a hit. Admire the city’s medieval architecture as you walk along the walls of fortified cities.

You will find the Alma Mater, the oldest university in Europe, which was founded in the 11th Century. You will be amazed at the complex architecture of the Basilica of San Francesco, Piazza Malpighi, and Piazza San Domenico. Don’t miss out on the chance to dine in some of Italy’s best restaurants!

8. Roccantica

Be prepared to be charmed and enchanted by the maze of staircases in Roccantica. Its cobbles and grey stones contain hundreds of years worth of history. It is also only an hour from Rome!

Santa Caterina is a typical middle-aged church, and you will fall in love with its simplicity. Attend the August medieval festival in the town – it’s a magical sight!

9. Pitigliano Alongside San Giminiano

Pitigliano is a medieval town in Tuscany Italy. Because of its many medieval buildings, it is well-known. Pitigliano is home to the Cathedral of Santi Pietro e Paolo and Pitigliano. The church of Santa Maria or the Orsini Forttress are also landmarks. If you’re still looking for amazing medieval experiences, the town is worth a visit.

We hear Bergamo is a great medieval town in Tuscany Italy. If you’re willing to do the extra mile, why not take a trip to both?

10. Verona

Verona is well-known for hosting the story of Romeo and Juliet. It actually showcases its historical richness through some of the most beautiful architecture. There are many amazing cathedrals, churches and piazzas. It is one the most beautiful medieval cities in Italy and has a feel that takes you back to the Middle-Age.

Enjoy the best of local cuisine and wander the streets of this city, which proudly boasts being one of the most beautiful medieval towns in Italy.

We have compiled 10 of the most beautiful medieval cities in Italy

Here it is – a list with 10 of the most beautiful medieval cities in Italy. Each one is rich with history, wars and architecture. It is a joy to explore new medieval cities in Italy. You can be you, or someone else, there. It is possible to discover the best of Italian culture and get lost in centuries-old streets. If you prefer to be on the beach, why not visit one of the most popular summer vacation destinations in Italy. We will be back!

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