The region of Castiglione was already occupied in prehistory and developed in the Etruscan era as early as the 6th century BC as a crossroads between the two cities of Arezzo and Cortona. The center was located on the hill near the current dungeon. The Etruscans embellished the whole of the Val di Chiana, like in Brolio.
Under the Republic, the Romans exploited the fertility of the region for their needs, but with the reign of Augustus, the flooding of the Tiber in Rome led the Romans to obstruct its tributaries, including the Clanis. This caused a stagnation of water which made the valley unsafe.
A free commune in the twelfth century, in the Middle Ages and up to the Renaissance, Castiglion suffered wars between the great neighboring communes such as Siena, Florence and Perugia.
Monuments in Castiglion Fiorentino
- The Communal Palace (XIVth), erected during the domination of Perugia
- The Pinacoteca Communale, in the old Sant’Angelo church.
- The Tour del Cassero, on the hill, rebuilt in the 14th century and of Etruscan origin.
- The Palazzo Pretorio (1412), housing the Municipal Library and the Archaeological Museum.
- The Loggia del Vasari (1513 and then revised), on the Piazza del Municipio.
- The communal theater, beginning of the 20th century.
- Church of San Francesco, Roman-Gothic, end of the 13th century.
- Pieve di San Giuliano (15th) and its collegiate church (19th century).
- Church of Sant’Agostino (14th century).
- Church of the Madonna della Consolazione (completed in 1607).
- Church of the Gesù (XVIth).
- Church of the Madonna delle Grazie del Rivaio (XVII)
- Church of Sant’Angelo al Cassero (12th century) with friezes by Giorgio Vasari.
- Church of Santa Chiara (XVIth).
- Church of Santo Stefano (or San Lazzo), built by the Company of Santo Stefano in the fourteenth century.
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