Castiglion Fiorentino - In the Heart of the Valdichiana
Situated on a hill in the Valdichiana,
Castiglion Fiorentino boasts Etruscan origins. A 1014 written document testifies the existence of the town under the name of Castillione Aretino for the first time. At the time, this part of Tuscany belonged to the Bourbon del Monte family but then it passed in the hands of Arezzo, which built new city walls in the years 1220-1250.
Florence conquered Castiglion Fiorentino defeating Arezzo in Campaldino. During the 14th century Arezzo, Florence and Perugia governed the town in turn. Thus, the town changed its name several times and called Castiglione Aretino, Fiorentino or Perugino, according to the ruling city. Castiglion Fiorentino passed definitively in Florence hands in 1384 and assumed its present name.
Castiglion Fiorentino has maintained its Medieval structure. The city walls dating back to the 13h and 14th centuries still surround the historical centre. The
logge del Vasari (Vasari`s loggia) open onto piazza del Municipio. Some local artists built them in the 16th century in Vasari`s style. The loggia is decorated with terracotta and stone reproductions of the coats of arms of the podestą that ruled the town and with a fresco representing the Annunciation. Opposite the loggia there is the
Palazzo Comunale (Town Hall), which was built in the 16th century and partly restored in 1935.
Of the ancient
Donjon dating back to the 11th-12th centuries only the tower and the
church of Sant`Angelo remain. The church was built in the 12th century and houses a
Madonna with Child and Saints by Giorgio Vasari, a fragment of a
Majesty by Taddeo Gaddi, two paintings by Bartolomeo della Gatta and beautiful gold and silver objects.

Castiglion Fiorentino
Three churches open onto the square at the end of vicolo Repente. The Neoclassical
Collegiate church of San Giuliano was built between 1849 and 1853 and is decorated with a
Madonna on the Throne with Saints by Bartolomeo della Gatta and paintings by Lorenzo di Credi and Segna di Bonaventura. The
Pieve Vecchia (Old Parish Church) was built in 1451 and is decorated with a
Deposition by Luca Signorelli and a terracotta by one of the Della Robbias. The
church del Gesł is decorated with paitings by Poppi and Francesco Vanni.
The
church of San Francesco is a Romanesque building featuring some Gothic elements. It houses a wooden crucifix by Giambologna and 14th and 15th century frescoes.
The building of the
church of Madonna della Consolazione ended in 1607. The octagonal church may have been designed by Antonio da Sangallo the Younger. It houses a
Madonna with Child attributed to Luca Signorelli.