Castello di Montegrossoli: A Medieval Fortress in Tuscany
Site at a Glance
- Rating
- 4.6
- Popularity
- Very Low
- Country
- Italy
- Primary era
- Medieval
- External website
- Open
- Eras represented
- Medieval
- Civilizations
- Holy Roman Empire
- Site type
- Military
- Remains
- Castle
On this page9 sections
History
Castello di Montegrossoli is a medieval military stronghold in Italy, near Gaiole in Chianti in Tuscany. Built during the eleventh and twelfth centuries, it is first documented in 1007. The fortress stood on a summit in the Chianti Mountains at about 700 metres above sea level, near the boundary between the territories of Florence and Arezzo. From this position, it controlled the area between Chianti and the upper Valdarno.
The Firidolfi and Florentine Conflict
The Firidolfi family acquired Montegrossoli and made it the centre of their activities in the area. These included brigandage and the plundering of goods travelling along the road below the fortress. The family supported the Ghibelline cause, whose adherents backed the Holy Roman Emperor in the medieval struggles between imperial and papal factions in Italy.
Florentine forces captured Montegrossoli in 1172 and compelled the Firidolfi to expel the imperial legate. Florentine control did not last. The Firidolfi rebuilt the fortress and strengthened its defences, subsequently repelling further Florentine attacks with their armed forces.
In the summer of 1182, Spinello Firidolfi and his sons Pepus, Scolaio, and Spinello junior attacked and plundered a convoy of 50 mules carrying grain. Florence was suffering famine, and the incident became the pretext for a renewed war. Florentine troops soon recaptured Montegrossoli and demolished the castle down to its foundations.
Imperial and Florentine Control
Its strategic value led to a rapid rebuilding, after which the Firidolfi again occupied the castle. Montegrossoli formed part of a defensive line supporting the emperor’s adherents. The Holy Roman Emperor Frederick Barbarossa, who ruled from 1155 to 1190, incorporated it into a military chain that also included the fortresses of San Miniato, Fucecchio, Pogni, and Semifonte.
In 1197, Florence purchased the castle from the Da Montegrossoli, ending the war. One branch of the family moved to the Castle of Radda in Chianti and adopted the surname Da Radda. The nobles of Radda later appeared among the Ghibelline families banned from Florence in 1268 and remained in Florentine lists of magnate families until 1415.
In 1220, the Holy Roman Emperor Frederick II, who ruled from 1220 to 1250, ordered the restoration of former imperial fiefs to their previous feudal lords, whether those territories had been seized by force or obtained through a regular sale. The Da Montegrossoli therefore returned to Montegrossoli and remained there until Frederick II’s death in 1250. The Florentine commune then repossessed the castle.
Destruction and Abandonment
Aragonese troops besieged Montegrossoli in 1478. In 1530, troops of Charles V, the sixteenth-century Holy Roman Emperor and king of Spain, conquered the fortress and definitively razed it to prevent the Republic of Florence from using it as a base to reconquer the Chianti area. The castle was abandoned after this final destruction and remains a ruin.
Remains
Surviving Fortress Structures
Enclosing Walls
The fortress occupies the crest of a mountain ridge. Its enclosing walls survive as scattered stones around the foot of the site, where vegetation covers much of the masonry. These fragments mark the outer boundary of the former stronghold.
Central Keep
The central keep, or cassero, was the fortified inner keep and principal defensive building of the castle. Its entrance door is raised above the surrounding ground and gives access to the interior. Stone capitals that once supported the floors remain visible inside the structure.
Northern Rooms
Several rooms in the northern part of the complex retain the remains of vaulted ceilings. Together with the keep and the scattered wall stones, these fragments survive in an abandoned condition and form the present ruin of Castello di Montegrossoli.

