In the determination of the modalities of settlement of the Asso’s valley. It has had a considerable importance the phenomenon of the Medieval fortifications. It is interesting to mark how all the main inhabited centres of the community of San Giovanni d’Asso keep till nowadays the characteristics of the fortified settlement of the Middle Ages. Moreover, if we look at the toponymy, we can see that in the area there are plenty of castles and elevated areas with toponymies which can be tracked down on Germanic characters, which testify the origin of the settlement: Montelifré(from “Liutfrid”), Montisi(from “Ghiso”) and Monterongrifoli( from “Grifo”). An important fortified centre was Montisi(already Monteghisi), which originally belonged to the Scialenhi Cacciaconti, who, even if they recognized the political control of Siena since 1175, they kept on practising their signory on the castle until the end of the XIII century, not without contrasts, also violent, with the local communities . in the XIV century Montisi became the seat of a vicarship which was elected by the citizens and which had its jurisdiction also on the near castle of Montelifré. Classic fortified-rise settlement, Montisi develops all around a hill, at the top of which there is a Cassero, remarkably worked over. In the built-up area we can see two following circles of walls, the most ancient of which is very fragmented. Also the castle of Montelifré belongs to the Scialenghi and it is mentioned only starting from 1213, when the local community of the castle made as if to submit to the commune of Siena. The fortifications of Montelifré would have been destroyed in 1289, for deliberation of the General Council of Siena: but maybe the action was not current or the castle was soon rebuilt. In a not specified time, they would have asserted at the ancient castle the possessions of the “noble family Martinozzi from Siena, derived by a Martinozzo from Montepulciano, which arose at the beginning of the XIV century (REPETTI). In 1526, after the battle of Camollia, the fortress of Montelifré, which is unfortunately on the way to a progressive decay, so that it is not possible anymore to understand where the entrance or any other functional element, which show partly the original covering with calcareous stone-rows. On the foot of them, on the south-eastern side, there is the lowest part of the castle, enclosed into a circle of walls with a tower in the middle and on which it has risen a group of houses. In the walls there are two opposite gates: one is south-westwards with the vestibule and the other one ,north-eastwards, they were originally linked by an extraordinary characteristic way, of which today it rests only about two thirds; in fact, towards the north-eastern door, it has been built a farmhouse which interrupts it, obliging to enter it by means of a small lateral lane, so that the ancient gate is now used only to enter the courtyard of the mentioned house, while the entrance to the village has been moved towards the fortress.

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