5 Must-see castles in the province of Arezzo

Unmissable Castles in the Province of Arezzo: a Journey into History

The province of Arezzo preserves a heritage of castles and fortified villages among the most fascinating in Tuscany. From the valleys of Casentino, rich in medieval towers and ancient strongholds of the Guidi Counts, to Val di Chiana with its mighty defensive walls, up to Valtiberina, land of battles and legends, every corner tells centuries of history.

These manors were not only places of defense but also centers of political and economic power, guardians of artworks, imposing architecture, and centuries-old traditions. Walking through their walls means reliving the Middle Ages, imagining ladies, knights, and the epic clashes between Guelphs and Ghibellines that marked these lands.

In this itinerary, we will discover some of the most fascinating and best-preserved castles in the province, ideal destinations for those who love history, architecture, and Tuscan landscapes.

Castle of the Guidi Counts in Poppi

The Castle of the Guidi Counts, the undisputed symbol of Casentino, dominates the medieval village of Poppi from the top of the hill. Built between the 11th and 12th centuries and renovated in the 13th century, it was the residence of the Guidi Counts and inspired the design of Florence’s Palazzo Vecchio. It hosted Dante Alighieri during his exile and houses the precious Rilliana Library with ancient manuscripts.

Inside you can admire the Chapel frescoed by Taddeo Gaddi, the noble halls, and the Hall of Festivals. From its panoramic tower, you can enjoy an extraordinary view over Casentino and the surrounding hills.

Castle of Romena

The Castle of Romena, located near Pratovecchio, is one of the most fascinating places in Casentino. Founded around the year 1000 and expanded by the Guidi Counts, it played a strategic role in controlling trade routes towards northern Tuscany and Romagna.

It also hosted Dante Alighieri during his exile, linking its name to Italian literary history. Today you can admire the surviving towers, the remains of the walls, and the evocative Piazza d’Armi. Not far away stands the splendid Pieve di San Pietro in Romena, a Romanesque masterpiece that completes the visit in a timeless atmosphere.

Poggio del Drago: the ideal base for exploring the castles of the province of Arezzo

The B&B Country House Poggio del Drago is the perfect starting point to discover the most beautiful castles in the province of Arezzo. Located along the scenic Wine Road, just a few kilometers from the center of Arezzo and in a strategic position to reach Casentino, Val di Chiana, and Valtiberina, it offers the possibility of organizing day trips to discover fortified villages and medieval strongholds.

After a day among historic walls and breathtaking views, guests can relax in the swimming pool overlooking the Tuscan hills or stroll through the large park surrounded by oaks and olive trees. The rooms, well-furnished and comfortable, ensure rest and tranquility, while the included breakfast allows you to start the day at best.

The family atmosphere and warm welcome make Poggio del Drago an ideal choice for a stay dedicated to history, nature, and authentic Tuscan hospitality.

Castle of Porciano

The Castle of Porciano, located in the territory of Stia, is one of the oldest and most fascinating testimonies of Casentino. Its origins date back to the early decades of the year 1000, and it was owned by the Guidi Counts for centuries. In addition to its strategic importance, it is linked to local legends, including the evocative tale of a golden bell hidden within its walls.

Dante Alighieri also stayed here during his exile, finding hospitality. Today it hosts a small museum with archaeological finds and historical evidence, offering a splendid panoramic view of the mountains and surrounding valleys.

Castle of Montecchio Vesponi

The Castle of Montecchio Vesponi, located near Castiglion Fiorentino, is one of the best-preserved medieval fortresses in Tuscany. Its origins date back to the 10th century, and the structure, with its characteristic 30-meter-high tower, has remained almost intact over the centuries.

Thanks to its strategic position between Val di Chiana and Val di Chio, it was long contested between Florence, Arezzo, and Perugia. The castle is linked to the figure of the English mercenary John Hawkwood (Giovanni Acuto), who used it as a military base in the 14th century. Today, although privately owned, it can be admired from the outside in all its grandeur.

Castle of Gargonza

The Castle of Gargonza, in the territory of Monte San Savino, is a perfectly preserved medieval fortified village and one of the most interesting castles, immersed in a wooded area overlooking Val di Chiana. The first evidence dates back to the 12th century, and over time it was contested between Arezzo, Siena, and Florence.

Famous for having hosted Dante Alighieri during his exile, it still preserves its walls, crenellated tower, and the ancient church of Saints Tiburzio and Susanna. Today, Gargonza is a charming tourist village, with stone houses transformed into apartments and suites, ideal for those seeking peace, history, and evocative views of the Tuscan countryside.

Your ideal stay begins at Poggio del Drago

After exploring castles, fortified villages, and breathtaking landscapes in the province of Arezzo, the B&B Country House Poggio del Drago is the perfect place to relax. Immersed in greenery, with a panoramic swimming pool and large outdoor spaces, it offers cozy rooms equipped with every comfort.

Its strategic location allows you to easily visit all the valleys of Arezzo and return in the evening to an oasis of tranquility. The warm hospitality of Emanuele and Filippo makes every stay special. Book your room now and experience authentic Tuscany, where history, nature, and relaxation meet in perfect balance.