
Tuscany · Arezzo
Castiglion Fiorentino
A walled hill townbetween Arezzo and Cortona, where Etruscan walls support the medieval Cassero and Vasari's loggia frames the Val di Chiana below.
59 km / 37 mi
Nearest hub (Perugia)
12,918
Population
Apr–Oct
Best time to visit
Recognised as
Why come
Castiglion Fiorentino sitsbetween Arezzo and Cortona, on a hill overlooking the fertile Val di Chiana. The centro storico is built on Etruscan foundations: excavations beneath the Piazzale del Cassero have uncovered the remains of a fourth-century BC city wall and sacred area. The Cassero, the medieval fortified core at the top of the town with its high tower, is grafted directly onto that earlier structure and remains the symbol of the place. The Logge del Vasari, a tripartite arcade on Piazza del Municipio designed by Giorgio Vasari in 1565 and built between 1570 and 1583, opens through three round arches onto a view that runs from the Val di Chiana to the Apennine ridge beyond. The Pinacoteca Comunale next door holds works by Bartolomeo della Gatta, Margaritone d'Arezzo and Taddeo Gaddi. The town carried allegiance first to Perugia, then to Florence from 1384, and was renamed Castiglion Fiorentino at that moment.
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Gallery
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Known for
Cassero
Medieval fortified core at the top of the town, with the high tower that is the town's symbol, built on Etruscan fourth-century BC foundations.
Logge del Vasari
Tripartite arcade on Piazza del Municipio designed by Giorgio Vasari in 1565, built 1570-1583, opening through three arches onto the Val di Chiana.
Pinacoteca Comunale
Civic gallery next to the Logge with works by Bartolomeo della Gatta, Margaritone d'Arezzo, Taddeo Gaddi and a notable bust reliquary in gilded silver.
Area archeologica del Cassero
Excavations beneath Piazzale del Cassero with Etruscan city wall and sacred area from the fourth century BC, visited on guided tour.
Pieve di San Giuliano
Sixteenth-century parish church on the main piazza, with a tabernacle attributed to Andrea della Robbia and a Renaissance organ.
Chiesa del Gesù
Renaissance church on the upper terrace, with a Crucifixion attributed to Bartolomeo della Gatta and frescoes from the fifteenth century.
When to visit
Best months · Apr–Oct
- J
- F
- M
- A
- M
- J
- J
- A
- S
- O
- N
- D
- Best
- Hot or crowded
- Quiet
- Mostly closed
April through June and September into October are the working months in the Val di Chiana: dry days, mild evenings, harvest of olives and Sangiovese into October. July and August push past thirty degrees and the plain below holds the heat; the town at 342 meters runs a few degrees cooler. The Palio dei Rioni in mid-June fills the streets with banners between the four historic quarters and a horse race in the Cassero square. November through March is quiet. The Vasari loggia in low winter sun, the three arches framing the Val di Chiana under cloud, is the view that does not appear on every postcard.
How to get there
From Perugia, Castiglion Fiorentino is roughly 59 km by road. Allow about 51–71 minutes depending on traffic and route choice (autostrada vs scenic).
Drive time to the nearest gateway airports
- Bologna2h 13m
- Ancona / Pescara2h 26m
- Florence / Pisa2h 27m
Elevation 342 m
Reachable by train
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Close by
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