Tuscany · Arezzo
Castiglion Fiorentino
A walled hill town between Arezzo and Cortona, where Etruscan walls support the medieval Cassero.
- Best time
- Apr–Oct
- By car
- 51 min from Perugia
- By train
- Station in the comune
- Population
- 12,918
Known for
CASSERO
Medieval fortified core with high tower grafted onto Etruscan fourth-century BC walls, the visual symbol of the town from the Val di Chiana below.
LOGGE DEL VASARI
Vasari's tripartite arcade designed 1565 and built 1570-1583 on Piazza del Municipio, framing the Val di Chiana view through three round arches.
ETRUSCAN ORIGINS
Fourth-century BC walls and sacred area beneath the Cassero, uncovered in excavations and visited as the Area archeologica del Cassero.
When to visit
Best · Apr–Oct
- J10°
- F12°
- M14°
- A17°
- M22°
- J28°
- J32°
- A32°
- S26°
- O21°
- N14°
- D11°
- Best
- Hot or crowded
- Quiet
- Mostly closed
Daytime averages, 2020–2024. Weather data by Open-Meteo.com.
The festa: Michele, 29 September
Why come
The hill stands between Arezzo and Cortona, above the fertile plain that gives the area its name. The centro storico is layered directly on what came before it: the medieval streets and the fortress at the summit sit on foundations from the fourth century BC, so walking from the lower gates to the top of the town is also a climb through the town's own construction history, one period built on the next rather than beside it. The upper terrace holds the oldest religious building along with the fortress, while the main piazza lower down gathers the later additions, the parish church, the arcade, and the gallery, into a single civic space.
The town carried allegiance first to Perugia, then to Florence from 1384, and was renamed at that moment, a change of name that marks the point where the additions to the skyline, the arcade among them, became possible. What results is a town where the sightlines do the explaining: the arcade frames the plain because the plain was always the reason to build here, and the fortress crowns the hill because it was already fortified ground long before anyone called it that.
The Sunday letter
Castiglion Fiorentino is on our list. Its letter is still to come.
We are writing about all 1,000 of these towns, one at a time, in a free letter every Sunday: the photo, the food, the festa. That is our mission. Sign up and you will be there when Castiglion Fiorentino comes up. By Peter & Sophia, from Pietrasanta.
Read on
Castiglion Fiorentino in our articles
The best hill towns in the province of Arezzo7 towns, Castiglion Fiorentino among them.
The best hidden olive oil towns you can reach by train within 90 minutes of Perugia9 towns, Castiglion Fiorentino among them.
10 Tuscan wine towns near Florence10 towns, Castiglion Fiorentino among them.
The 10 best towns you can reach by train that hold a food festival within 90 minutes of Perugia10 towns, Castiglion Fiorentino among them.
How to get there
From Bologna (BLQ), about 2h 13m by car.
Ancona / Pescara (AOI) is about 2h 26m away.
By car from the centre of Perugia 51 minutes, Siena 1h 8m or Florence 1h 14m.
There is a railway station in the comune, so you can arrive without a car.
Coming from Florence, Bologna or Pisa?
Coming by train into Perugia? Castiglion Fiorentino is about 48 minutes away by road.
What to see
Cassero
Fortified core at the top of the town. The tower is reached by climbing through the streets of the centro storico, with the drop toward the plain opening out only at the top.
Logge del Vasari
The three arches sit at the edge of Piazza del Municipio, so the arcade functions as a frame for the view rather than a monument to walk around. Below it, the Pinacoteca occupies the neighboring building.
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
The wall and sacred area lie underground, reached on a guided tour that descends beneath the piazzale rather than crossing it at street level.
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.
The slow-trip planner
Building a trip? Find where Castiglion Fiorentino fits in a slow Italy circuit.
Answer five questions. We will shape a geographically coherent slow trip from the 1,000 Italian towns most travelers skip. Yours to save and share.
Through the year
What happens here
Feasts and festivals that come back year after year. We give the month rather than the date, because the date moves and the month rarely does. Check with the source before you plan a journey around one.
Palio dei Rioni di Castiglion Fiorentino (Arezzo)historical re-enactment
usually held in June. Borghi Toscana - Eventi
I Giorni di Baccofood festival
usually held in September. TrovaSagre
Living here
- Population 12,918
- In-betweeni
- Pharmacy in town
- High school within a 30-minute drive
- Train station in the comune
- Nearest airport Bologna, 2 h 13 min drive
- Regional capital Firenze, 1 h 14 min drive
Common questions
- What is Castiglion Fiorentino known for?
- Castiglion Fiorentino is a walled hill town at 342 meters between Arezzo and Cortona, where Etruscan walls support the medieval Cassero.
- Where is Castiglion Fiorentino?
- Castiglion Fiorentino is a comune in the province of Arezzo, in Tuscany.
- What is the nearest airport to Castiglion Fiorentino?
- Bologna (BLQ), about 2h 13m by car.
- Can you get to Castiglion Fiorentino without a car?
- Yes. There is a railway station in the comune, so you can arrive by train.
- How long is the drive from Perugia to Castiglion Fiorentino?
- About 51 minutes by car.
- When is the best time to visit Castiglion Fiorentino?
- Best in Apr–Oct. July is the warmest month, averaging 32 degrees, and December the wettest, with about 12 rain days.
- Is there a sagra or a festival in Castiglion Fiorentino?
- Yes. Palio dei Rioni di Castiglion Fiorentino (Arezzo) and I Giorni di Bacco. June is when the first of them falls.
- Which other towns are like Castiglion Fiorentino?
- Todi, Urbino and San Severino Marche.
- How many people live in Castiglion Fiorentino?
- 12,918 at the 2023 count.
Tags & datadesignations · numbers · sources
Recognised as
The numbers
- Elevation: 342 m
- Population: 12,918
- Surface area: 111.58 km²
These figures were compiled from public directories: ISTAT, OpenStreetMap and Wikidata, and from the official listings of the guides named on this page. Town details change; verify with official sources before you travel.
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