Montegrossi Castle

How to reach

What remains of the castle rises on the crest of a relief at the border between the Chianti and the Valdarno. From Florence, Montegrossi can be reached by leaving A1 at the exit 'Valdarno' and then from Montevarchi, following the indications to Cavriglia-Gaiole. After about fifteen kilometers, just before the road begins to come down toward Gaiole, we will find on the left the road signals that bring us to the village of Montegrossi. To reach the ruins, it is necessary to leave the car and to follow a path that departs from the wood on the left of the last curve of the road that brings to the small village of Montegrossi.


The castle of Montegrossi, also known as Montegrossoli, was the sentinel and last rampart of the medieval feudal system constituted in the Chianti region. Erected at around 700 meters high on the crest of the last relief of the small mountain chain on the border between the territories of the Chianti and the Valdarno, a perennial object of disputes between Florence and its enemies, the castle dominates the pass and the road that connects the two areas and also a big part of the valleys from both sides.

The first notices of the small fortress are from the year 1007; in 1172, it was conquered and destroyed by the Florentine, who wanted to free their movements in the zone from a big obstacle. After a few years, the rest of the castle became the fief of the Firidolfi family, which took care of its reconstruction. There are notices that these vassals also used Montegrossi as a base for actions of brigandage and looting of the caravans direct to Florence. A little afterwards, the castle entered to make part, as an important stronghold, of the chain of fortifications wanted by the emperor Barbarossa from the Chianti to Fucecchio, in the low Valdarno, to control central Tuscany. But a few years later, during the war between the League of the Tuscan Communes and the imperial armies, the Florentines took back possession of the castle. Montegrossi was strengthened and, due to its strategic importance, was gifted a permanent garrison.

In the following centuries, Montegrossi was many times, with great fury, besieged. The strongest attacks were brought first by the Aragonese Army in 1478 and then in 1530 by the army of Charles V°, which definitely leveled the castle to the ground to avoid that the defeated Florentine Republic was once again able to use it as a point of strength for the Chianti. Since then, the ruins of Montegrossi were abandoned, but on the crest of the mountain still rises the mighty keep, surrounded by the walls, which unfortunately only shed stones in the vegetation, of the fortified enclosure. On the keep, we can still notice the beautiful gate of access, at a raised level from the ground, and at the interior, the capitals of stone that sustained the batten of the attic. In the northern part, the residence for the garrison, we can see in some locals the rest of the stone ceiling. Unfortunately, the whole complex is at serious risk of collapse, so much so that a visit could also be dangerous. 

Despite its scarce rest, the presence of the castle cannot pass even today unobserved to whom transits from the Valdarno to the Chianti or vice versa. The better view we can have of it is from the near Coltibuono Abbey, site on the Arno valley slope of the pass, while to realize the strategic importance of Montegrossi, all it takes is climbing 'til the ruins and letting space the view to 360 degrees. Today, the castle shows its northern side on an artificial precipice provoked by a cave of stone, that has also defaced the surrounding landscape.