Culture Travel

The Most Exceptional Medieval Italian Towns

These medieval places are a must see during your next visit to Italy.

The Middle Ages, also known and Medieval Times, was an era that started on a grim foot. The Roman Empire collapsed, and Italy was facing political turmoil as other countries began invading and fighting over the vast expanse of lands. However, by the time the Renaissance arrived, the country was reestablishing itself and was starting to thrive. 

During these hard times, the country managed to build some of the most beautiful cities that are still around today. Here are the ten most outstanding towns that the Italian Middle Ages gave its citizens.

San Gimignano


Named a UNESCO World Heritage Site, San Gimignano was said to have been settled by two brothers who were fleeing Rome. By the time the Middle Ages arrived, the town was still only a small village under the control of the bishop of Volterra. However, due to its desirable position on the route to Rome, San Gimignano quickly grew and established itself in the trading world. They experienced a decline in the 14th-century, but the city eventually found its footing again and worked to preserve much of the Medieval architecture it is known for today. 



Siena is one of the most beautiful Medieval towns in the country. The city was said to be founded by the son of Remus, one of the founders of Rome. During the Middle Ages, Siena’s now-famous Piazza del Campo was rebuilt to represent the nine members of the ruling democratic group at the time and to symbolize the Madonna’s cape that protected the city. Aside from the Piazza, the city’s popular attractions include the Duomo of Siena and Torre del Mangia. 



Made famous by Stephanie Meyer’s book series Twilight, Volterra was the home of the deadly vampire family the Volturi. In real life, Volterra is a welcoming haven for artisans and is known for its production of alabaster. The area was once an important city-state in the Etruscan Empire and was home to an episcopal lord during the Middle Ages. 



Located just 90 miles outside of Rome, Orvieto sits high atop a hill overlooking the surrounding plains. The town is divided into two sections: the new town, which is located at the bottom of the hill, and the old town at the top. Old Town is where you will find all of Orvieto’s Medieval charm such as the Duomo di Orvieto and the Palazzi Papali. The city also has an impressive network of underground caves where visitors can see an old olive press and a former pigeon coop. 



As a city bursting with gorgeous palaces and historic churches, Montepulciano is not a city to be missed. The area is surrounded by acres of vineyards and is known for some of the finest winemaking. Inside the town, you should start at the Piazza Grande, which has been the primary gather spot for citizens for centuries. The city’s oldest church, the Church of Sant’Agostino, was built during the Middle Ages and holds many historical works of art. 



Home to one of the country’s oldest university, Perugia is a vibrant city that hosts annual events like Umbria Jazz and a chocolate festival. As the capital of the Umbria region, this area has a long history dating back to the Etruscans. During the Middle Ages, the University of Perugia allowed the citizens to flourish and cemented them as a cultural center for the arts.



Guarded against the outside world by towering stone walls, Monteriggioni was built as a fortress to protect against armies from Siena. There are 14 original guard towers along the walls, and the layout of the village inside has barely changed since it was first built during the Middle Ages. The town is known for its annual Medieval Festival, where people dress up in costumes and take part in mock duels and live performances. They also have storytellers and local artisans featured throughout the day, along with an array of ancient foods. 


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: