The Ultimate Medieval Castles Tour in Italy: live history from Emilia-Romagna to Tuscany

Castles are undoubtedly among our favorite architectural treasures. Majestic and imposing, they offer breathtaking views from their towers and evoke a fairytale-like and romantic atmosphere.

While we’ve previously focused on specific areas or regions, in this journey we’d like to broaden our horizons and include some territories rich in castles. We’re inviting you on this ultimate Medieval Castles Tour in Italy, starting from Emilia-Romagna and ending in Tuscany.

Hop in the car with us, fasten your seatbelt, and discover the epic stops we’ve selected for Italian Castles off the beaten path, to let you relive the magic of Medieval Italy.

Our exploration of Medieval Castles in Italy begins in the central-northern part of the country, between Emilia-Romagna and Tuscany. This area has witnessed pivotal events and battles and the rise and fall of powerful noble families, whose legacies still echo through these buildings. It is also a land of fascinating geographical variety, featuring the Apennines, rolling hills, valleys, lush forests, and even stretches of coastline (in this case, the Adriatic on). Though this journey spans two different regions, our goal is to celebrate our glorious past through these awe-inspiring structures.

This road trip will take you to some of the best castles to visit in Italy for history lovers, across seven stops in seven days, traveling by car along an imaginary route from Gropparello Castle near Piacenza to Monteriggioni in the province of Siena.

We're going to start from the Medieval Park of Gropparello Castle, a place off the beaten track for tourists, but at the same time famous and much loved by Italian people. We will focus on a romantic and magic place, where the architecture blends with the surrounding nature, which represents an unmissable opportunity for those who want to take a walk back in time, immersed in a picture-perfect panorama. But also for those who have always dreamed of fully living the experience of visiting and staying in a real Italian Medieval Castle at least for one night. 

Let's discover together all the must-see stops on our tour of Medieval castles in Italy. 

Among the historical places to visit in Italy, in particular Medieval Castles, the Gropparello Castle, in the town of the same name near Piacenza, is a must.

Let’s begin our path by arriving in Piacenza by train, then hop in our car to reach this quaint village, about 30 km away.

Perched on a hill and surrounded by the lush scenery of the Vezzeno Gorge, the castle immediately reveals its military origins—a fortress built to ward off enemies, now impeccably preserved.

Also known as Rocca di Cagnano, the castle dates back to the 9th century, though it may have been a Roman outpost even earlier. It was built by order of Bishop Giuliano II, allegedly with the blessing of Charlemagne himself. Later, it became the stage for conflicts between the Guelphs and Ghibellines, a common fate for fortresses along the Tuscan-Emilian Apennines.

Like any authentic Medieval castle, Gropparello has its tales of courtly love and restless spirits. According to legend, around 1200, when the castle was part of Lord Pietrone di Cagnano's fiefdom, his wife Lady Rosania betrayed him with the commander Lancillotto Anguissola, and was therefore locked up forever in a walled room. Some people swear that still today the mysterious ghost of the noblewoman haunts the castle.

If you are not curious enough yet, you’ll be glad to know you can stay overnight in the luxurious and comfortable Torre del Barbagianni (Owl Tower) suite. But you can also take part in hikes in the neighboring woods, to admire the beauty of the Vezzeno gorges, or discover the events and historical re-enactments, among knights, ladies, ogres and witches. You can also enjoy the best of Italian and Emilian cuisine, famous candy-shaped tortelli and tasty local cured meats, in the Medieval Tavern, a Slow Food presidium and well-known winery of local labels.

The Fairy Tale Park of Gropparello Castle will make you live the splendor and greatness of the Italian Middle Ages, but also the experience of being in a fantasy. And so, among reenactments and animations, experiences and tournaments, dream and reality, you will be able to take a real journey to a great time. You will also be embraced in the natural beauty of the Vezzeno Gorge surrounding the complex, whether you are in couples, friends or with your family.

The Fairy Tale Park and its magical atmosphere come to life from March to November, on Sundays and holidays only, making it the ideal place for an alternative and unforgettable weekend getaway. But if you want to carve out a few hours of romance with your sweetheart, you should know that the Torre del Barbagianni, the Castle and the Medieval Tavern await you all year round.

On the second day, we head to Canossa, just a few kilometers from Reggio Emilia. A quick drive gets us to this village of about 3,000 residents, nestled in the “Matildic Lands”, once ruled by the powerful Lombard Countess Matilde di Canossa — an art patron, skilled politician, and staunch supporter of the Pope.

This castle was the residence of the noblewoman, and it became famous for the so-called Humiliation of Canossa: the Germanic emperor Henry IV begged Pope Gregory VI to revoke his excommunication, and to do so he remained on his knees in the snow, his head covered with ashes, outside the castle walls, until the countess took pity on him by receiving him to grant him the pope's pardon. Therefore, the building is not only a trace of Countess Matilde's greatness, but also an important reference point for medieval Emilian and Italian history.

Built in the 10th century and restored several times, the castle fell into disrepair after the feudal system was abolished in the 17th century. Though partly in ruins, it remains a National Italian Monument, and visiting it offers a moving connection to this extraordinary chapter of medieval history.

On day three of our tour of the Medieval Castles in Italy, we drive for about an hour toward Vignola, near Modena.

The town is very famous for its delicious cherries and one of the most beautiful, well-preserved castles to visit in Italy for history lovers.

Rocca di Vignola probably dates back to the 10th century, built by the Vignola family after the fall of the Carolingian Empire to be a protection against Barbarian invasions. It was restored at the behest of successive dynasties, the Este and especially the Contrari, whose greatness it testifies to.

Today it is possible to visit this splendid example of medieval architecture with the whole family, to relive the dreamlike atmosphere it evokes, entering the famous Chapel of Uguccione Contrari, where beautiful frescoes are located, the opulent and huge halls, and, of course, walking along the walls.

On day four, for our fourth stop, we approach the Riviera Romagnola and for our Italian castle experience we head inland to Cesena. Here we can visit the impressive Malatesta Fortress, built in the late 14th century by the powerful Malatesta family that ruled the region from the 13th to the 17th century.

The fortress stands on Garampo Hill, overlooking the lush Parco della Rimembranza and giving a view all the way to the Adriatic Sea.

The castle remains in great condition due to countless restorations along the centuries and offers a true dive into Romagna's Medieval era. In summer, it's also a family-friendly castle, with events, festivals, and markets in its courtyards.

On day five, we move to Tuscany, to the Casentino Valley near Arezzo, where we find the town of Poppi. Here you really have to visit the Castle of the Counts Guidi, rulers of the area from the 12th to the 15th century - where some say that even Dante Alighieri stayed for a night or two.

The fortress was probably built at the beginning of the Guidi rule, at least according to written records, but over the centuries it underwent several modifications. To enter the structure you will experience the thrill of walking on a bridge suspended over a moat. Inside you can visit splendid halls, the Chapel with very rare frescoes, and the Rilliana Library, which collects the priceless heritage of 25000 ancient volumes of Count Fabrizio Rilli Orsini, lord of the area in the 19th century.

Still today, this castle plays an active role in the life of the town, serving as Poppi’s municipal council chamber.

We have reached the sixth day of our immersive experience in Italy's medieval castles, and from Poppi we proceed into Chianti, toward Siena, to visit two splendid castles.

In the morning we reach the small town of Gaiole in Chianti in a couple of hours, heading for Brolio Castle. This enchanting manor was owned and cared for by the Ricasoli barons, who still maintain it today, so you can admire it in its integrity and grandeur. In addition to the magnificent outdoor spaces and sumptuous interiors furnished with priceless family heirlooms, the beautiful 16th-century Italian-style garden, where the director Bernardo Bertolucci shot some scenes of Stealing Beauty, is not to be missed.

Here, since the early 1990s, the Ricasoli family has established its winery there, resuming the centuries-old tradition of wine production, and their delicious Chianti Classico is exported all over the world. Of course, a visit to the castle can be cheered up with winetastings of Ricasoli's prized bottles directly in the area dedicated to the cellars; it is also possible to be led through the vineyard at the base of the building, enjoy Sienese cuisine in the castle's tavern, and stay in the charming hotels just a short walk from it.

For the seventh and final day of our vacation in Italian Tuscan castles we remain in Chianti and in about 40 minutes from Gaiole we reach the Castle of Monteriggioni. It is a town of 10,000 inhabitants, just 20 km from Siena, surrounded by a splendid city wall.

Built around 1217 to mark an important stop along the Via Francigena, it was the venue for battles between Guelphs and Ghibellines and rivaled Florence for its dominance. It was also the scene of later battles, ending up among the properties of the Medici family and the Visconti family, who included the territory in their duchy. As witness therefore to the passage of these two legendary Householders, the castle shelters within it a wonderful village with a carefully preserved historic center, overlooking the lush Sienese countryside.

Wandering through this fabulous place provides a true journey through time, accompanied by the sounds of the surrounding nature and an immersive and authentic experience. We therefore end our day and our tour here.

Whether you're passionate about history or simply curious to know what it’s like to sleep in a real medieval castle, the fortresses we’ve explored offer the perfect alternative getaway, ideal for couples or families.

Discovering Italian history through the stories of those who shaped it is a fascinating way to connect with our heritage. Now you just have to book your car and pack your bags!