[3][4] Documents from the 10th century mention a town named "Castiglione" in the feudal property of the Marquis of Monte Santa Maria.

In 1369, the townspeople revolted against the Perugians,[5] giving themselves to the Papal States; by 1384 the Florentines seized the town and bestowed its current name, Castiglione Fiorentino.

During the 15th century, Castiglion Fiorentino suffered from repeated outbreaks of the plague, blamed at the time on the marshy areas surrounding the city.

After the Congress of Vienna in 1815, the town was returned to Tuscany, to which it remained until 1861, when the Grand Duchy was annexed to the newly created Kingdom of Italy.

Situated on a hilltop, 345 metres (1,132 ft) above sea level, the town overlooks the Val di Chio and the Preappenines.

Similar to the festival in Siena, the Palio dei Rioni is a horse race around Piazza Garibaldi, including a colourful and energetic display of the ancient custom of flag-waving, which dates back to the 13th century.

During the week leading up to Easter Sunday, the parade along the city's streets, re-enacting a scene from the Passion as they have done annually for the past four hundred years.

[6] 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 traveller any time of the year.

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.