The town of Castiglione Fiorentino is in the province of Arezzo at 342 m. a.s.l. and it has a population of about 12,000 inhabitants. The church of St. Francis, the "Pieve Vecchia" (XVI century), the Municipal Picture Gallery and the Palazzo Pretorio, where some Etruscan finds are kept, can be admired in the town.

The town of Castiglion Fiorentino was known and inhabited in very remote times, but an important permanent settlement developed in the Etruscan times, above all, between the V and the IV century b.C. Once the Romans had conquered the area, they provided for its territorial organization with the centuriation and the division of land in farms where the first villas rose. The paludification of the Valdichiana, the, caused the inhabitants to move towards the hills around it. This is how the first villages and parishes were born.
One first trace of Castiglione dates to the X century and it is known that it was a feud belonging to the marquises of the Monte Santa Maria at the time. In the following centuries, the emperor and the bishopric of Arezzo shared the control of the area and the latter actually controlled it directly. In its period of communal autonomy, Castiglione had some difficulties in imposing its independence because of the pressure exercised by the more powerful nearby centres. After the defeat of Arezzo in Campaldino in 1289, the village passed under the Florentine dominion and took its current name.
The hugest fortification of the city took place only after Arezzo, led by the Bishop Guido Tarlati, conquered it again in 1303. When the "primate", Arezzo's lord, died the Florentines conquered Castiglione again (1336). In 1344, the inhabitants of Perugia besieged the village and it changed its name into Castiglion Perugino. During the troubled XIV century, the change of seigniory took place twice more. In 1369, the town submitted to the State of the Church to avoid the domination of Perugia, while in 1384 Florence finally reaffirmed its dominion on the town.
Despite the political stability of Castiglione, the threat of plague spread in the area. Once this difficult moment was overcome, Castiglion Fiorentino was again at the centre of a dispute between Florence and its rivals and Piero Strozzi also annexed and governed it for a short time on behalf of the Sienese republic.
In 1554, the town was definitively annexed to the Grand Duchy of Tuscany, thanks to which it lived in peace and its agriculture developed thanks to the reclamations the Lorraine settled in 1765. Yet, the town was one of the first to revolt against the Lorraine seigniory, the first time when the French arrived here in 1799, then with the Risorgimento uprisings and its annexation to Italy in 1860.