The remains of the castle are on the ridge of a relief on the border between the Chianti and the Valdarno. From Florence you can reach quickly leaving the A1 at the Valdarno exit and following the directions for Cavriglia-Gaiole from Montevarchi. After about fifteen kilometers of ascent, just before the road begins to descend towards Gaiole, we will find on the left the junction that leads to Montegrossi.
The castle of Montegrossi, also known as Montegrossoli, was the sentinel and last bastion of the medieval feudal system established in Chianti. Built about 700 meters high on the crest of the last relief of the small mountain chain that acts as the border between the territories of Chianti and the Upper Valdarno, always the subject of disputes between Florence and its enemies, dominates the pass and the road that connects the two areas, besides a large part of the valley both on one side and on the other.
The first news of the fortress is in 1007, in 1172 it was conquered and destroyed by the Florentines who wanted to get rid of a major obstacle to their movements in the area. After a few years the remains of the castle became a fief of the Firidolfi family from Chianti, who took care of its reconstruction. There are reports that these feudatories also used Montegrossi as a basis for actions of brigandage and looting of caravans heading for Florence. Shortly afterwards, the castle became part of the chain of fortifications built by the Emperor Barbarossa from Chianti to Fucecchio, in the Lower Valdarno, to control all of central Tuscany.
But even this domination did not last long, and during the war between the League of Tuscan Municipalities and the imperial forces, the Florentines took back the fortress. In addition to a strengthening of defense systems, the fortress, given its strategic importance, was equipped with a permanent garrison.