This historic Tuscan Town lies at the center of a triangle formed by important cities such as Florence, Siena and Perugia.
Castiglion Fiorentino, originally an Etruscan settlement and later an old medieval village, lies close to the famous Valdichiana and Cortona.
The tower of the ancient castle dominates the town. This charismatic town has much to offer any visitor including its beautiful medieval walls, beautiful churches, art treasures and numerous Renaissance structures - e.g. the Loggia by Vasari at the Piazza del Municipio.
The first of the existing city walls, including Porta Fiorentina, the main entrance to the town's historical center, was erected in the 13th century, then enlarged in the 14th under the Perugians to connect the castle to the outside walls. An anti-gate containing the Medici coat of arms is located outside of the walls, while the inside of the gate is constructed of three arches under a statue of the town's patron saint, St. Michael. The town's fortress, the Cassero, was completed in 1367. In the 15th century, the nuns of San Girolamo used the fortress as a convent, and by the 19th century much of the fortress had been destroyed, with the remaining structure used as a prison
The Pinacoteca, or Municipal Art Gallery, occupies the former church of Sant'Angelo. Built on the site of an Etruscan temple, the church of Sant'Angelo was built in Romanesque style between 1229 and 1239. The church has served as a hospital, wine cellar, and workshop before being renovated and used as an official museum and art gallery
Castiglion also has many festivals throughout the year including the famous "Palio dei Rioni" on the third Sunday of June. A smaller version of the similar festival in Siena, the Palio dei Rioni is a horse race around Piazza Garibaldi, including a colorful display of the ancient custom of flag-waving, which dates back to the 13th century.
In addition to the spring poppies, summer sunflowers and the famous Tuscan Cypress and Olive trees the beautiful green hillsides and country lanes are a must for any traveler any time of the year.