Volpaia
Discover Volpaia
Last updated on October 16, 2026Introduction
Volpaia is a frazione of the comune of Radda in Chianti, in the province of Siena: a fortified borgo of medieval origin at 617 metres, with 49 inhabitants.
The castle probably arose around the 10th century, like others scattered across the landscape of the upper Val di Pesa, and it arose where it did — on the crest of one of the hills running from the Badia a Montemuro towards Radda — because, standing on the watershed of two small valleys formed by tributaries of the Pesa, it was easily defensible.
The first document to mention it was drawn up at Cintoia on 21 April 1172: it records that the brothers Franculus and Galfredus da Cintoia took out a loan of 28 pounds of silver from Spinello da Montegrossoli, mortgaging their possessions, which lay in the curte et castello de Vulpaio.
Politically it was Florentine. The borgo fell within the judicaria florentina from the eleventh century, and when Florence organised its territory into Leagues in 1250, Volpaia found itself in the Lega del Chianti, among the peoples of the Terzo di Radda.
Architecture
The plan was an ellipse with towers. The fortification consisted of a wall circuit on a roughly elliptical plan, alternating with defensive towers; the largest of them, beside the entrance gate, must have functioned as the keep.
What stands. Some stretches of the original walls, the powerful main tower on a rectangular plan, and one of the minor towers.
The cylindrical turret is the exception and the evidence. On the north side, its masonry a sasso accapezzato differs from the filaretto of the castle's older parts, so it is a later addition — probably after 1478, when round towers came into favour as better able to take artillery fire.
The internal street is the organising line. A road ran through the castle along its major axis, splitting it into two nearly equal halves, with the gate at the street's head. The gate is gone, lost in the alterations to the whole south-west sector of the walls, but it is still drawn in a cabreo of 1801; in that same sector there are notable remains of medieval buildings incorporated into houses.
Dating is hard because the castle has no ornament. The total absence of architecturally ambitious passages or sculptural decoration makes a precise date for the castle remains problematic. What settles it is the masonry: in the oldest walls, characterised by a perfect filaretto facing, the fortification can be traced to the first half of the twelfth century.
The late-Renaissance doorways are the disarmament. Several open into dwellings inside the castle, and they record the moment the place stopped being a fortress and became a village.
How it was built and evolved over time
The building stone came from next door. Because of the proximity of several sandstone quarries — worked until a few years ago — the construction is predominantly of that stone, and that is what gives Volpaia its brown-gold aspect, unusual in the Chianti, where the solar clarity of alberese prevails even in fortifications.
Filaretto is the technique that dates it. The oldest walls are characterised by a perfect filaretto facing — small squared blocks laid in regular courses — and on that basis the fortification is placed in the first half of the twelfth century.
The later work is visibly rougher. The cylindrical turret on the north side is built a sasso accapezzato, roughly trimmed stone, which is how it can be told apart from the twelfth-century fabric at a glance.
The church shows the same reading. San Lorenzo's right flank coincides with a stretch of the wall circuit and is not faced in sandstone filaretto like the castle's older parts; instead it shows irregular masonry in which well-chiselled blocks of white alberese — perhaps the residue of a pre-existing Romanesque chapel — alternate with fragments of sandstone.
The Ospedaletto is brick and filaretto together. Inside, the structure has brick arches and walls formed of large stones laid in filaretto, with a large incised sandstone block over a window.
Frequently asked questions
What happened here in 1478?
The Sienese and Aragonese took Volpaia in August, as part of the second Aragonese invasion. Before the month was out the castle rebelled, expelled the garrison and sent the Sienese commissioner Cipriano to Florence as a prisoner. The allies stormed it again on 2 September; the Florentines retook it on 7 October.
How old is the castle?
It probably arose around the 10th century; its oldest masonry, in perfect sandstone filaretto, dates the fortification to the first half of the twelfth century. The first document naming it was drawn up on 21 April 1172.
Why does it look different from other Chianti villages?
Sandstone. Quarries nearby meant the castle was built predominantly of arenaria, giving it a brown-gold colour unusual in a district where the pale alberese limestone prevails.
Can I just walk in?
Yes — it is a public hamlet with forty-nine residents. Nobody publishes hours or a ticket. The wine estate inside it, though, is a working business.
What is the Ospedaletto?
A hospital for pilgrims, built around 1400 at the centre of the castle, on the road linking the upper Pesa valley with the Valdarno. A sandstone lintel carries the incised Cross of Malta. It is now used as a cellar.
And the church with the blocked round window?
The old church of San Lorenzo, inside the walls, deconsecrated when a new church was built for Volpaia. One of the castle's towers served as its bell tower.
What is the most important building here?
The Commenda di Sant'Eufrosino, built 1443–1460, a National Monument since 1982 and the most important piece of Renaissance architecture in the Chianti.
