How to reach
What remains of the castle rise on the crest of a relief at the border between the Chianti and the Valdarno. From Florence Montegrossi can be reached leaving A1 to 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 brings us to the castle.
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, 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 of the year 1007, in 1172 it was conquered and destroyed by the Florentine that wanted to free their movements in the zone from a big obstacle. After few years the rests of the castle became fief of the Firidolfi family, that took care of its reconstruction. There are notices that these vassals also used Montegrossi as base for actions of brigandage and looting of the caravans direct to Florence. A little afterwards the castle entered to make part, as 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 again posses of the castle. Montegrossi was strengthened and, due to its strategic importance, was gifted of 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 from the army of Charles V° that leveled definitely the castle to the ground, to avoid that the defeated Florentine Republic was once able to use it again as point of strength of 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, unfortunately only shed stones in the vegetation, of the fortified enclosure. On the keep we can be still able to 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 rests of the stone ceiling. Unfortunately the whole complex is in serious risk of ulterior collapses, so much that also a visit could be dangerous. To reach the ruins 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 asphalted road that brings to the small suburb of Montegrossi.
Despite its scarce rests the presence of the castle cannot pass even today unobserved to whom transits from the Valdarno to the Chianti or viceversa. 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 what was the strategic importance of Montegrossi all it takes is climbing 'til the ruins and let 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.