The Most Beautiful Medieval Towns In Italy

As you explore the streets of any Italian city you’ll quickly notice that many buildings, ruins and monuments seem to look as though they come from deep in the mists of time, which often they do. The most obvious features that you’ll see are the ancient stone walls that surround the historic centers of cities but there’s a whole range of medieval remains that survive to this day.

A Brief Overview Of Medieval Italy.

The Medieval Period, also known as the Middle Ages, lasted from the 5th Century AD until the late 15th Century AD. This 1000 year period was extremely tumultuous and saw numerous wars, famines and plagues ravage Italy and much of Western Europe. However, paradoxically, the Medieval Period was also an amazing time for the development of art, architecture, literature and culture which culminated in the birth of the Renaissance in Florence in the 14th Century AD.

During the Medieval Period, Italy was divided into dozens of small city states. These were autonomous regions that were each dominated by a main city from where the economic, political, cultural and religious life was organized. To protect these centers of power, the cities built large stone walls, many of which remain intact to the present day!

But it wasn’t just impressive city walls that were built in the 1000 years that spanned the Italian Medieval Period. For instance, some of Italy’s most iconic churches and cathedrals were built in the Middle Ages, including the Cathedral of Milan and Saint Mark’s Basilica in Venice.

The Medieval Period in Italy began in earnest with the fall of the Western Roman Empire in the 5th Century. The period ended with the birth of the Renaissance and ultimately, with the emergence of the Age of Discovery which was spearheaded by wealthy city states such as Venice and Rome.

The result of this remarkable period in Italian history is a plethora of magnificent art and culture that is preserved in some of the country’s smaller cities. This is because in the huge metropolises, such as Rome and Milan, much of the medieval past has been swamped by modern developments whereas in the smaller cities the historic past is still preserved in full view.

The Most Beautiful Medieval Towns In Italy.

The following are the best medieval towns in Italy:

Civita Di Bagnoregio, Viterbo.

This is one of the most surreal medieval cities that you can visit in Italy because the only way you can enter it is by means of a medieval footbridge! The 300 ft bridge spans the deep valley of Calanchy and would have made the city nearly impregnable to an invading army.

For modern tourists, the bridge offers spectacular views and although you have to pay a small fee to cross it this helps with its upkeep and maintenance. Fortunately, once you get within the city walls you’ll find many hotels, restaurants, museums and shops that will welcome you with open arms, unlike the invading armies of the Middle Ages.

Siena, Tuscany.

Siena is one of Italy’s most beautiful cities and is best known for its Gothic cathedral that stands overlooking the streets below. Within the impressive cathedral, you can marvel at some of the finest works of art by legends such as Michelangelo and Donatello or join a guided tour to learn all about the history of the area.

As well as the Siena cathedral the Piazza del Campo was also built in the Middle Ages and still hosts a bare-backed horse race that first took place in the 14th Century! Riders from the city’s various districts race around the square each July and August, attracting huge crowds of tourists and locals to the exciting event. During the race, known as the Palio di Siena, street vendors set up stalls, restaurants stay open late and fancy dress carnival floats complete the party atmosphere.

Roccantica, Lazio.

Roccantica is a small medieval city just 50km north of Rome. Often overlooked by tourists, the city’s two Gothic churches, the Santa Caterina and the San Valentin, are wonderful examples of perfectly preserved medieval architecture that are worth visiting the city to see. The Santa Caterina also houses 14th Century frescoes that are popular with tourists who make the trip to Roccantica.

Other major attractions in Roccantica include the Roseto Vacunae Rosae which is a beautiful spiral garden that contains more than 5,000 varieties of roses and 9 grand fountains. The city is also home to the Tenuta La Tacita, a gorgeous palace that hosts weddings and other special events.

Stilo, Calabria.

Stilo is a small Calabrian city that is best known for its oil, cheeses and wines. As you explore the city’s medieval architecture the place can feel like an insect that has been perfectly preserved in amber! In 2001, Stilo was voted one of the country’s most beautiful cities by the ‘I Borghi più Belli d’Italia’, a national association that was established to promote Italy’s historical legacy.

The city’s most remarkable building is the Cattolica di Stilo, which is a stunning Byzantine cathedral that has an almost totally unique design, with pergola-like spires that overlook the valley below. The medieval castle and the Duomo of Stilo are also a must-see for visitors who are interested in the city’s ancient past.

San Gimignano, Tuscany.

Nicknamed the ‘Medieval Manhattan’ due the number of large medieval towers that dominate the city’s skyline, San Gimignano is a spectacular example of the ambition of the city’s medieval architects. Of course, these towers originally served as defensive structures and lookout posts but today they are a popular tourist attraction.

From the top of the city’s iconic towers, you will get some of the best views in the province of the surrounding Tuscan countryside. The city’s historic center also retains its medieval atmosphere with small cobblestone streets, traditional family-run restaurants and vendors selling local produce in open-air markets!

Ferrara, Emilia-Romagna.

Ferrara is a UNESCO World Heritage Site that is made up of elegantly broad streets and stunning early Renaissance-era churches and buildings. Ferrara represents the very best of the Medieval Period and although it was established in the 6th Century on the ruins of a Etruscan settlement it has continued to flourish unto the present day.

Ferrara was a major hub of art, culture and cuisine, even during the Middle Ages. The city was best known for its Cappellacci di Zucca, which is a unique hat-shaped pasta that is filled with locally grown pumpkin. While you are in Ferrara you must make sure to visit the Al Brindisi wine bar, which was established in 1435 and is officially the oldest in the world!

Verona, Veneto.

As the inspiration for Shakespeare’s Romeo and Juliet, Verona is Italy’s ‘city of love’ and one of the country’s top tourist destinations. Verona is steeped in history and has a magnificent medieval heritage that includes churches, cathedrals, castles and piazzas.

From the 13th to 14th Centuries the city of Verona was ruled by the famous della Scala family during which it experienced some of its greatest prosperity and growth. During this time, numerous churches, palaces and castles were built, many of which remain almost perfectly preserved. As the city grew wealthy and powerful, it became a major medieval center for art and culture, securing its place as one of Italy’s great medieval monuments to the historic past.

Verona is a UNESCO World Heritage Site and is home to a multitude of cultural attractions. The Centro Storico, or the ‘historic center’, includes many of the major sites including Juliet’s House, the Verona Arena, the Torre dei Lamberti and the Piazza del Erbe which hosts an outdoor market that was already thriving during the Middle Ages!

Bologna, Emilia-Romagna.

Bologna is the 7th largest city in Italy and the capital of Emilia-Romagna. Bologna was founded as a Etruscan city, named Felsina, which was later captured by the Celts and renamed Bona. Eventually, it was conquered by the Romans but then after the fall of the Western Empire, it became a free city state at the start of the Medieval Period. During the Medieval Period, Bologna flourished and was one of the largest cities in Western Europe!

The city’s historic center is extremely well preserved and is home to a multitude of beautiful churches, towers and porticoes. Bologna is also the site of the oldest university in Europe, the University of Bologna, which was founded in 1088 AD! In 2000 Bologna was voted the European City of Culture, in 2006 it received the UNESCO City of Music award and in 2021 it was named a UNESCO World Heritage Site.

Truly, one of the most remarkable medieval cities in Europe, Bologna is a spectacular example of how some parts of Italy managed to thrive throughout the difficult times of the Middle Ages.

Italy’s Medieval Past Is A Cultural And Historic Goldmine.

The Middle Ages in Italy played a vital role in creating the foundations for the birth of the Renaissance as well as other major architectural and artistic movements that repeatedly swept through Europe. Long before Italy was even a unified state, the artistic, religious and cultural life of the city states drew on similar roots and created one of the wealthiest, powerful and influential regions in the Western world.

Visiting Italy’s medieval cities and exploring their unique heritage is a fascinating way to learn about how the Middle Ages changed the entire course of European history. Tragically, huge swathes of medieval European cities were reduced to rubble during the Second World War but in Italy the damage was extremely limited compared to Germany, Austria or France.

As a result, Italy remained one of the few countries in the world where the true magnificence of the European Medieval Period could still be seen first hand. From Gothic cathedrals to early Renaissance churches, from priceless medieval frescoes to the looming watchtowers that still stand guard over the ancient cities, no trip to Italy would be complete without taking the time to appreciate the incredible legacy that the craftsmen of the Middle Ages left to future generations.

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