Castiglion Fiorentino is a historical village in the province of Arezzo and overlooking the Val di Chiana. The town’s ancient origins date back to the Etruscans, who assiduously first inhabited it, and then to Roman times. Archaeological excavations in the village’s square have uncovered a sacred area dating back to the 5th century BC.
The medieval city walls overlooked by the Cassero fortress are almost intact.
The remote town, built on a hill that stretches between the Clanis valley and the Chio valley, has developed over the centuries, being heavily favoured for its strategic position. The historic centre, which is situated right between the cities of Arezzo and Cortona, dominated both the roads heading north and the cross-sectional roads towards the Nestore valley and the upper Valtiberina.
Surveys carried out in 1988 led to the identification of an Etruscan Oppidum which was at its height of power between the Archaic and Hellenistic ages, leaving traces of an authentic Etruscan centre.
The medieval village is also awarded the Orange Flag of the Touring Club.
The village starts from Porta Fiorentina, the centuries-old entrance in the north of the village that leads to the historical centre. Just beyond the square is the Church of San Francesco, a fascinating Romanesque building with the occasional Gothic element, dating back to the second half of the 13th century.
Take a visit to the Piazza del Municipio, where you’ll find the Municipal Picture Gallery housed in the Church of Sant'Angelo; treasured 13th century goldsmith's works and some valuable paintings by Margarito, Taddeo Gaddi, Bartolomeo della Gatta and Giorgio Vasari are also kept here.
Vasari's 16th century loggia, dating back to 1513, is just opposite the Palazzo Comunale. From this architecturally astounding spot you can take in the stunning view of the Val di Chio along with Valdichiana and Valtiberina.
The Civic Archaeological and Underground Archaeological Excavation Museum is another important monument located inside Palazzo Pretorio. The museum collects archaeological relics found in the Castillian and Cassero areas. The partial reconstruction of an Etruscan sanctuary’s roof is particularly interesting and dates back to between the end of the 5th and the beginning of the 4th century BC.
The Museum of Sacred Art of the Pieve (or Collegiata dei Santi Michele e Giuliano) is also well worth a visit, housing works from the 15th and 17th centuries, including the fresco Mourning over the Dead Christ by Luca Signorelli and an altarpiece by the Della Robbia workshop depicting the Baptism of Christ.
Among the multitude of other attractions in Castiglion Fiorentino, we recommend taking a trip to the Municipal Theatre, a beautiful structure with three tiers of platforms. The inside is decorated in a beautiful nineteenth-century style, with refined golden stuccoes and elegant marbled plaster.
The wider Valdichiana territory is incredibly picturesque and perfect for a 5-day stay among historical villages; for a more authentic experience, stay in one of the Tuscan countryside farmhouses. A leg of the Via Romea also passes through Castiglion Fiorentino, going all the way from Arezzo.
Also nearby is the small hamlet Manciano, or La Misericordia as the Castiglionese like to call it, where the actor Roberto Benigni was born.
Spring is an ideal time to visit Castiglion Fiorentino, when the popular Maggio Castiglionese - a month full of events – takes place.
The third Sunday of June is instead dedicated to the Palio dei Rioni Castiglionesi, a horse race that takes place in Piazza Garibaldi, just outside the city walls.
The Terre di Arezzo Wine Route extends for 200 kilometres, passing through Castiglion Fiorentino: the Arezzo area boasts a DOCG Chianti Colli Aretini and 3 DOC wines – Cortona, Valcichiana and Val d’Arno di Sopra - in red, rosé, white and vinsanto. Besides vegetables and cheeses, the region produces fabulous honey and an excellent extra virgin olive oil; its meats and sausages are also renowned.