Arezzo: 3-Day Itinerary of Castles and Medieval Villages from Cortona to Poppi

The Co-Cathedral of Santa Maria Assunta rises majestically in Piazza del Duomo, the heart of Cortona. Built on an ancient Romanesque parish church, its Renaissance facade conceals a Gothic interior housing precious artworks. The high altar features Lorenzo di Niccolò Gerini's Triptych, a 15th-century panel painting that narrates Marian stories with vibrant colors. In the left chapel, the 4th-century Roman sarcophagus bears witness to the site's historical layers. Climbing the external staircase leads to the crypt with medieval columns, while the bell tower offers a panoramic view over the Valdichiana. For those following the 'Borghi e Castelli Arezzo' itinerary, this is the perfect stop to immerse yourself in Cortona's atmosphere, between Tuscan spirituality and art.

The Girifalco Fortress, built by the Medici in the 16th century, towers over Cortona offering breathtaking panoramas of the Valdichiana valley. Its strategic position makes it a privileged observation point, with imposing walls and bastions that tell centuries of history. Ascending Via di Fortezza, you'll reach the entrance where exploration of the walkways and towers begins. Inside, temporary exhibition spaces enrich the visit, while the outdoor area is perfect for taking photos with views over Cortona's medieval rooftops and the Tuscan hills. Admission requires a ticket, but it includes entry to the local museum when combined. I recommend checking the opening hours on the official website, as they vary seasonally. The structure is well-preserved, with informative panels explaining its defensive function and transformations over time.

Leaving the Fortezza del Girifalco behind, the second day of our itinerary begins with Montecchio Vesponi Castle, a 14th-century jewel standing isolated on a hill amidst the fields of Castiglion Fiorentino. Its structure has remained almost intact, with crenellated walls and towers that tell the story of the Knights of Malta and the condottiero John Hawkwood. Climbing up Via di Montecchio, you reach the entrance where you can admire the panoramic view over the Valdichiana, with rows of cypress trees and villages in the distance. Inside, the patrol walkways and halls preserve traces of frescoes, while the exterior invites you to take photos with the imposing main tower. Access requires a ticket, but it includes a printed guide with historical details. I recommend checking the opening hours online, as visits are often guided and subject to seasonal variations. The isolated location makes the castle a tranquil place, perfect for immersing yourself in the medieval atmosphere without crowds.

The Cassero Tower rises in the heart of Castiglion Fiorentino, a landmark of the medieval village. Built in the 13th century as part of the defensive system, it now offers a unique panoramic view over the Valdichiana and surrounding hills. Climbing its 40-meter height, you'll appreciate original architectural details like arrow slits and stone corbels. The tower is connected to the Municipal Palace through the covered passageway, evidence of the ancient fortified structure. From the upper terrace, the gaze stretches as far as Cortona and Lake Trasimeno, making the climb particularly rewarding. Its strategic position along the itinerary of Arezzo's hilltop villages makes it an unmissable stop for those wanting to capture the essence of the territory.

The Guidi Counts Castle stands majestically over Ponte a Poppi, a symbol of feudal power in the Casentino region. Built between the 11th and 12th centuries, it preserves intact defensive structures such as the crenellated walls and the central keep. Inside, visitors discover spaces like the armory and prisons that tell centuries of local history. From the courtyard, you can enjoy a spectacular view of the valley and the Arno River, while the towers offer glimpses of the village rooftops. Its strategic position along the itinerary of Arezzo's castles makes it a reference point for those exploring the area, with architectural details showing the evolution from medieval origins to Renaissance interventions.

Romena Castle rises imposingly on a hill near Pratovecchio, offering spectacular views over the Casentino valley. Built in the 11th century, this manor is one of the most important in the province of Arezzo, with its defensive walls, three towers and keep still well preserved. Inside, you can visit the prisons, the chapel and the rooms once inhabited by the Guidi counts. Dante Alighieri stayed here during his exile, and it's said he found inspiration here for some verses of the Divine Comedy. Today, the castle is a museum that tells the story of medieval life and the historical events of the area, with artifacts and explanatory panels. The isolated location and evocative atmosphere make it perfect for those seeking a plunge into the past, away from the crowds. I recommend exploring the surroundings too, where unpaved trails lead to panoramic spots ideal for memorable photos.