10 Most Beautiful Medieval Towns In Italy

This list of beautiful medieval towns in Italy has been compiled by Lisa Franceschini, an Italian mom passionate about travel and writing.

To those who, like me, are passionate about medieval architecture, Italy offers nearly endless satisfaction. 

Just a few dozen kilometers away from the largest cities, one can stumble upon wonderful Italian medieval towns that dominate the surrounding landscape from privileged positions atop hills or flat rock spurs. 

Having been born and raised in central Italy, I’ve had the opportunity and the fortune to visit many of them, quenching my thirst for places beyond the beaten path where one can admire relaxing natural landscapes and taste high-quality local food. 

In this post, I will reveal the medieval villages of upper Lazio, such as Civita di Bagnoregio, “the suspended city,” and Calcata Vecchia, the town of artists. Then, I’ll move north to Tuscany in the Val d’Orcia, a UNESCO World Heritage countryside region that hosts the tranquil medieval village of Monticchiello. 

I’ll pass through the “town of fools,” Gubbio, one of my dearest places in the Umbria region, famous for its deeply felt popular traditions. But I will also talk about other towns in northern and southern Italy that are a pleasure to discover slowly.

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Italy’s Medieval History – A Brief Introduction

Medieval history began by convention in 476 AD when the “barbarian” Odoacer deposed Romulus Augustulus, the last emperor of the Western Roman Empire.

At that time, foreign populations from the north and east invaded Italy on several occasions: Vandals, Visigoths, Huns, Arabs, Normans, and Lombards.

Wealthier local families retreated to inaccessible and easily defensible places. They built fortresses surrounded by high, thick walls, where the common people also took refuge.

The clergy did the same, creating monasteries that were self-sufficient settlements.

This phenomenon has enabled us to have towns with excellently preserved medieval architecture.

Beautifully Preserved Medieval Towns in Italy

Civita di Bagnoregio

Although it’s a town in a central area of Italy, off the tourist radar, the image of Civita di Bagnoregio’s landscape has traveled the world. It is one of those small medieval European towns that came straight out of a fairy tale.

Imagine a flat spur of rock with warm, alternating colors like a lollipop, set in a landscape of light gray rocks that remind one of the moon’s surface. 

The peak of strangeness is when there’s fog; Civita truly seems to float in the void. Perhaps this is why Japanese anime designer Hayao Miyazaki was inspired by it to create the floating city in his “Laputa: Castle in the Sky.”

The first two times I visited Civita, I found few other travelers in the village, next to its roughly ten permanent residents. My mother, who was with me, detested it: she doesn’t like walking, yet to reach the historic center, one must walk for about half a mile. 

Then, one must cross a bridge that spans the valley for 300 meters: a delight for the eyes and spirit and definitely the highlight of the visit.

The last time I visited Civita, however, I encountered large groups of tourists; word has gotten out about its beauty. 

To get there by public transport, you must take a train to either Viterbo or Orvieto, take a local bus to Bagnoregio, and take another local bus to the square, from which you can start a roughly 20-minute walk. Once you reach the panoramic bridge, buy a €5 entrance ticket to the town.

✦ Pro Tip: Visit Civita on this wonderful full-day tour from Rome that includes lunch and wine tastings.

Calcata

Still in the Lazio region and about 60 km north of Rome, there is another town perched on a rock spur, which I think is even more beautiful than the one I just described. 

Calcata Vecchia is famous for hosting a community of artists who have lived here for almost three generations, starting in the 1960s. They came from other parts of Italy and the world, having heard about the beauty of the Treja Valley, today a nature reserve rich in lush forests.

Living just a few kilometers from this town, I visit it every week, especially on weekends when all the artists’ workshops, restaurants, and cafes are open.

You can enter Calcata through the only large gate at the top, where the remains of the medieval noble family Del Drago still exist. The gate is integrated into the remnants of the defensive walls.

Pause to look at the panorama from one of the many terraces of the town and listen to the pleasant gurgling of the Treja river, along with the chirping of birds flying over the majestic trees of the forest.

The most interesting architectural feature is that the houses are built on tuff rock, a volcanic stone that seems to merge with the foundations of the old buildings. The cellars of the homes are often ancient caves from the pre-Roman era. Staying in these houses is undoubtedly a unique experience.

In the morning and at sunset, the artists gather in the small square in front of the church in the historic center to share news or organize creative events like exhibitions or concerts.

Live music plays almost every evening at the Bardo House Gypsy Club. For food, we usually go to Ristorante La Piazzetta, which uses organic foods and serves exquisite tiramisu, a typical Roman dessert.

✦ Pro Tip: About an hour north of Calcata, you’ll find the mysterious Monsters Park in Bomarzo. Calcata and Bomarzo are often combined in a Rome day trip like this one.

San Gimignano

The medieval town of San Gimignano, a UNESCO World Heritage Site, is a beautiful Tuscan town that needs no introduction.

Tuscany is one of the most famous regions in Italy, and there is a saying that San Gimignano is the most beautiful town in Tuscany. It is one of the two medieval Italian towns most worth visiting in this region.

This town is best explored on foot. Head to the main square or choose to linger in the narrow alleys and buy authentic souvenirs such as oil, wine, pecorino cheese, and handicrafts from local vendors.

At the historic center, indulge in a cappuccino to accompany the view of beautiful medieval architecture. The number of towers will surprise you: originally, there were even more.

Enter the Duomo di San Gimignano to admire the town’s artistic jewel: 14th-century frescoes depicting biblical episodes covering all the walls.

It’s also worth walking along the perimeter of San Gimignano, partly on the walls, to enjoy the beauty of the Tuscan hills, which are beautiful in all seasons.

Every time I visit, I observe that tourism is growing rapidly, especially international tourism. I’m not surprised. Visit on a weekday to avoid some of the local tourism.

San Gimignano does not have a train station, but you can easily get there by bus from Poggibonsi or car along the A1 highway.

✦ Pro Tip: Visit San Gimignano on a full-day tour from Florence that includes wine tasting and lunch.

Monticchiello

Since Tuscany is less than 100 km from where I live, I visit twice a year. I take advantage of the low season in winter to go to the Val d’Orcia. This area is part of the UNESCO heritage for the excellent historical preservation of the rural landscape.

The landscapes of the Val d’Orcia are the most iconic of the Italian countryside north of Rome. Think of dirt roads lined with rows of cypresses leading to solitary farmhouses on top of a hill. 

I particularly love Monticchiello, a small town with medieval architecture and a tranquil atmosphere. Every time we visit, we meet a handful of locals, who are all very friendly.

It’s lovely to walk outside the walls and admire the surrounding hills. We also did this while our daughter was sleeping in the stroller.

Be sure to explore the gently sloping alleys leading to a garden with olive trees and contemporary sculptures that emphasize the magic of the place. 

The prominent historical landmark is the medieval Church of Santi Leonardi e Cristoforo, which has a finely carved marble entrance door and frescoes inside.

Gubbio

The Umbria region, in the heart of Italy and without any coastlines, is famous for its small towns and forests. One of the most underrated Umbrian towns is Gubbio, the “town of fools.”

The parents of a longtime friend of mine are both from Gubbio. They introduced me to Gubbio on its most important day, May 15th, when the Festa dei Ceri is held. 

I have attended other medieval reenactment festivals, but this one surpasses them all. On this day, the local people demonstrate their passion, pride, and capacity for emotion—it’s contagious. I’ve found myself moved to tears several times, carried away by the surreal atmosphere. 

The festival originated in the 12th century and celebrates Bishop Ubaldo Baldassini’s death. It consists of a competition among the three classes of local people: peasants, merchants, and clergy.

Three groups of local youths shoulder equally massive wooden structures and proceed through the alleys and squares of Gubbio along a predetermined route, followed by the people.

The festival’s ritual is very complex and includes costume parades, folk music, and more. The common denominator is the warmth of locals.

Even if you visit Gubbio at other times of the year, you won’t regret it. The historic center is located on the slopes of a mountain, and you can enjoy spectacular views of the lush Umbrian countryside.

Legend has it that if you visit the Fountain of Fools, you will earn the much-coveted “license of the fool,” worthy of a Gubbio citizen.

The heart of the town is the scenic Piazza Grande with the Palazzo dei Consoli, which houses the Civic Museum – absolutely not to be missed.

Gradara

Those passionate about literature may have heard of Dante Alighieri’s Inferno, part of the Divine Comedy, a masterpiece of Italian Middle Ages poetry dating back to the 13th century.

Like all my compatriots, I studied this book in school. One of the most famous episodes is the tragic story of Paolo and Francesca, two star-crossed lovers Dante tells about in Chant 5th.

Well, the protagonists of the love story gone wrong really existed, and the events took place in the village of Gradara.

This place’s fame and perfect conservation make Gradara one of the best medieval towns to visit in Italy.

Gradara is located about 150 km southeast of Bologna, in the Marche region, just a few kilometers from the Adriatic coast.

The town has received several official awards, such as being named the “Medieval Capital of Italy” and one of the “Most Beautiful Towns in Italy.”

Gradara Castle is one of the most famous castles in Italy. To learn more about the castle’s history, the tale of Paolo and Francesca, and the artistic treasures on display, you will want to join this guided tour that lasts about 2 hours, as we did.

The town, with its castle and courtyards, dominates a hill from which the view extends for miles to the coast.

The first step in discovering this medieval Italian town is to cross the front gate and walk through the alleys. During the summer, artistic and cultural events occur in the town several times a week: concerts, performances, poetry readings, and culinary workshops.

To reach Gradara, travel to Pesaro by train and then take Adriabus number 130 to Gradara.

Santarcangelo di Romagna

Located in the province of Rimini, Santarcangelo di Romagna is only some kilometers away from the sea. 

Those who love to explore offbeat attractions will not want to miss the tufa caves carved into the Giove Hill on which the town stands. Although their origin remains a mystery to this day, visiting its three floors gives the impression of experiencing underground cities that have been carefully planned down to the smallest detail. 

This lovely town in Romagna is the cradle of many poets and poetesses past and present, so much so that in 2015, it established a festival dedicated to poetry: “Cantiere Poetico.” 

Workshops, readings, and activities for young and old are held several times a year. These are inspired by literature and poetry born from the narrow streets furrowing the hill on which this medieval town stands.

You can get here by train, the station is conveniently located in the historic center, or by car via the A14 highway.

Abbateggio

With half of its territory covered by mountains and coast, Abruzzo is one of the lesser-known Italian regions.

In recent years, Abruzzo has often been the destination of our travels because it is hard to resist. It borders the region we live in, has pristine nature with 3 national parks, and the

The area of Abruzzo that has stayed most in our hearts is the Majella National Park, which revolves around Mount Majella and offers countless hiking trails for all levels. 

I will never forget the first time I visited the medieval village of Abbateggio in Abruzzo. It has just over 300 residents whose houses are all made of local stone. We spent several days there, visiting the woods around the village. 

Among the places that impressed us the most are – the Cusano Fall, which springs from a fissure in a large karst rock, channeling pure mountain water, and the Hermitage of San Bartolomeo, which you can reach by following the park’s trails.

If you visit in the summer, you might stumble upon the Spelt Festival, which celebrates the town’s typical food, including Abruzzese specialties like cheese, arrosticini, sautéed vegetables, and lake and sea fish.

I advise you to travel by car so you can visit other small towns in the vicinity, like Roccamorice and Caramanico Terme.

Castelsardo

The island of Sardinia, located in the center of the Mediterranean Sea, with its own language and a culture distinctly different from that of mainland Italy, is a true paradise for Italians. 

We Italians don’t need to fantasize about visiting the tropics because, within a short drive and a ferry ride, we can reach some of the most beautiful beaches in the world. I am referring to the beaches of Sardinia. Those traveling to Sardinia for the first time often find it difficult to leave the stunning beaches.

However, we followed the advice of friends who lived in Santa Teresa di Gallura, north of Sardinia, and went to Castelsardo. This town develops around the hill on which the medieval Doria Castle stands. 

The castle deserves a thorough visit. Inside, you’ll find the Museum of Mediterranean Weaving, where you can learn about the history of ancient Sardinian weaving techniques. The hand-woven fabrics and baskets will leave you amazed, so take a walk through the narrow lanes of the historic center to discover the craft shops: contemporary Sardinian women still practice weaving.

From the hill on which the town is situated, enjoy a splendid view of the northern coast of Sardinia. From Castelsardo, you can reach beautiful beaches on foot, such as Lu Bagnu Beach and Cala Ostina.

To reach Sardinia, take a ferry from a major Italian port like Civitavecchia and Piombino to Olbia. Then, rent a car to explore the coast and interior.

Erice

This journey through Italy’s medieval towns concludes at the biggest island that flanks the Italian peninsula: Sicily. 

At its westernmost tip stands the lovely Erice, one of the most beautiful places in Sicily.

Passing through Porta Trapani, we enter the small town perched on Mount San Giuliano, from which it took its name in the early 1900s. The name Erice was later given to it in honor of Eryx, a giant of Greek mythology.

A short scenic route leads to the Castle of Venus. Connected to the Balio Towers by a flight of steps (which became such only in the 1800s; previously, it was a drawbridge), the castle ruins date from Norman times, which in turn had been built on the remains of a temple dedicated to the female deity, Venus. 

Erice is not only history but also the sea. It boasts some of the most stunning beaches in Sicily, including San Giuliano Beach. 

Reaching the center of Erice by car may not be convenient because of the uphill and somewhat winding roads and the difficulty in finding parking on narrow streets. 

A fun and inexpensive alternative way to reach this beautiful southern Italian town is the cable car. The cable car starts in Trapani and takes you up to Porta Trapani.