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Tuscany Travel Guide



Castiglion Fiorentino is high interesting beautiful town situated on a green hillside of Valdichiana’s territory, between the cities of Arezzo and Cortona.

From Greek, Etruscan and Roman origins there have been found several important settlements located in its area coming from those ancient civilizations, conferring to the town a well-known archaeological grade into eastern Tuscany. Maybe the main one is a recently discovered sacred area from the 5th century BC.

Castiglion Fiorentino, former a medieval manor, is still preserving a ring of fortified walls overlooked by the “Cassero” (Castle) dated back from the 11-12th centuries c., when the manor was a property of the Marquis di Monte Santa Maria.
In the subsequently centuries the town, hardly and continuously contended, felt into the power of the Bishopric of Arezzo (last decade of the 12th century). Nevertheless, the Castle remained under the local jurisdiction of the Empire as certified by the documents signed up by the Emperors Arrigo VI (1196) and Federico II (1225). After the Bishopric Arezzo’s domination the town (named by them Castiglione Aretino) was overtook by Florence, consequently to the Aretino’s defeat during the Campaldino’s Battle (1289).
At the beginning of the 14th century the Bishop Guido Tarlati and his brother Pier Saccone re-conquered the town, returning it under the Empire’s local jurisdiction.
When Guido Tarlati died, Castiglione was briefly dominated again by the Florentines (1336- 1344). In the same year the town was conquered by Perugia, renamed it Castiglione Perugino. In the last two decades of the 14th century the town, after being for fourteen years under the jurisdiction of the Holy See (at the times of Pope Urbano V), passed with the whole Arezzo’s territory under the jurisdiction of Florence’s Republic, receiving its present name.
In the 16th century, at the times of the war between Florence and Sienna, Castiglione Fiorentino passed for a short time under the dominion of Piero Strozzi, returning under Florence’s power in 1554. It remained under their rule until the Medici’s dynasty extinction, passing subsequently under the dominion of the Lorena’s Dukes in 1765 who demanded for their Dukedom the whole Valdichiana’s territory. A long flourishing period for Castiglion Fiorentino and its area was started, reaching a strong demographic, economic and cultural development.

Main monuments to visit:

- Palazzo Pretorio (The Courthouse):  built up in the 15th century, many archaeological findings have been discovered during the excavations in the Piazzale (the Main Square rebuilt by Giorgio Vasari in the 16th century) where the Palace is located. An important part of those precious objects is exposed in it indoors as well as many other which were found in the town’s area. The Palace is also hosting the Municipal Library.
- The Municipal Art Gallery: is located on the first floor of the ancient Castle. It houses a rich collection of art works coming from ancient local chapels and churches, like a “Crucifixion” by Margarito d’Arezzo’s school (13th century); “The Madonna and Child” by Taddeo Gaddi (14th century); “The Stigmata of S. Francesco” and “The Stigmata of S. Michele”, both by Bartolomeo della Gatta (15th century); “The Madonna and Child and S.Giovannino” by Ridolfo del Ghirlandaio’s school (16th century); “The Madonna and Child and S. Anna” by Papacello (16th century) and “The Ecstasy of S. Teresa” by Gian Domenico Ferretti (16th century).
On the ground floor the large structure is also housing the beautiful Church of S. Angelo from the 13th century in Romanesque style, which hosts: a big Cross from the Umbrian school (13th century); two panels by Jacopo di Sellaio (15th century) and “The Virgin and Child and Saints” by Giorgio Vasari (16th century).  In the Crypt there are conserved important elements and objects coming from the archaeological excavations made in its undergrounds allowing the discovering of a Necropolis from the 3rd - 4th centuries BC.
Close to the Church is “The Hall of S. Orsola” hosting precious gold art works as well as “The Reliquary of S. Orsola” (14th century).
On the top of the Castle there is “The Tower Room”. Overlooking the town it keeps a very interesting collection of old coats of arms and commemorative inscriptions.
- The Castle of Montecchio Vesponi: situated in the nearness of the town is an imposing medieval defensive building granted by Florence to the condottiere Giovanni Acuto because of the victory of their army over the Aretino’s one during the Battle of Campaldino.

Where to eat:

- Ristorante “Da Muzzicone”. In the centre of the town, is a formal restaurant where enjoy a selected variety of traditional local and Tuscan dishes. Wine cellar is keeping a sort of remarkable local wines denominated “I Vini della Strada di Arezzo” as well as some Tuscan prestigious wines.
- Ristorante – Pizzeria “Roggi”. Decorated into a traditional Tuscan old fashioned style the structure is located in the old cantina of Palazzo Dragomanni. In the outdoors there is a pretty terrace for meals in season. Wine cellar is assorted by very good local and Tuscan wines.
- “Antica Trattoria La Foce”. Is a popular trattoria offering a tasty local traditional cuisine. Wine cellar hosts the well-known Arezzo’s province wines.

Main Towns of Valdichiana

Arezzo, Cortona , Montepulciano, Chianciano Terme, Chiusi, Torrita di Siena, Foiano, Castiglion Fiorentino, Lucignano

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