5 castles to visit in the Valdichiana around Arezzo

Lucignano marks the border between the territories of Siena and Arezzo, an absolutely privileged position in the heart of the Valdichiana confirmed, precisely, by the presence of the cassero.
The cassero's origin dates back to 1300, when Lucignano was under Sienese rule and its function was exclusively defensive: however, in the aftermath of the defeat of the Sienese at the Battle of Scannagallo, it took on the function of a grain storage and later housed a theater.
Opposite the fort is Piazza delle Logge, commissioned by Cosimo I de' Medici in the aftermath of the Battle of Scannagallo, for the urban completion of the town.

The Castle of Montecchio Vesponi is located in Castiglion Fiorentino and is a true medieval jewel that has remained intact over time, not only architecturally but also in terms of its atmosphere.
Its state of conservation makes it one of the most evocative forts in the whole of Tuscany: erected on a hill, on the borders of the Valdichiana, it served as a strategic point for controlling the ancient route between Arezzo and Cortona.
The imposing crenellated walls are 263 meters long with nine watchtowers, and its majesty was immortalized in some paintings by Beato Angelico.
Also extraordinary is the tower that soars about 30 meters.
Its strategic position placed the castle at the center of several battles between Arezzo and Florence: in 1289 it became a Florentine stronghold and took on its present appearance following a series of reinforcement works.
Later, in the 14th century, it became the fiefdom of the dreaded John Hawkwood, the famous Giovanni Acuto immortalized by Paolo Uccello in the imposing fresco in Santa Maria del Fiore in Florence.
Today, Montecchio Vesponi Castle hosts concerts, literary events and guided tours.

The Fortress of the Girifalco in Cortona, was built in 1556 at the highest point of the city at the behest of Cosimo I de' Medici.
The fortress rose on what was the old structure of an Etruscan, Roman and medieval fortification.
The building has a trapezoid shape with four large bastions and remains an interesting example of 16th-century military architecture.
Today the Fortress is one of Cortona's cultural venues, hosting events, hosting exhibitions and can be visited by appointment.
The view of the entire Valdichiana is extraordinary.

The Fortress of Civitella Val di Chiana is one of the greatest examples of forts of Lombard origin and was built between the 6th and 7th centuries.
In a strategic position in central Italy, exactly on one of the highest promontories in the area, it has long been a contested territory, precisely because it allowed for control over the surrounding valleys.
The village is enclosed by a medieval wall, elliptical in shape, and has a gateway - the Porta Aretina - that joins the fortress, a classic example of a castle-enclosure.

The historic center of Marciano della Chiana still has the distinctive features of a medieval castle of a defensive-military type: the perimeter and rectangular geometric layout, the city walls and the Clock Tower.
You cannot miss the scenic walkway leading to the Terrace over the Valdichiana, from where the splendid Tuscan valley can be admired in all its beauty.
At the moment, the Tower of Marciano can be visited by reservation only.