In determining the procedures for settlement of the valley dell'Asso had considerable weight phenomenon of medieval. And 'Interestingly, in this regard, as all major towns in the municipality of San Giovanni d'Asso serbino still dell'insediamento fortified character of the Middle Ages. Moreover, if we look at the place names, we find that abound in the area castles and offshore locations with names related to Germanic people, that unequivocally denounced the origin of installation: Montelifré (Liutfrid) Montisi (Ghiso) Monterongrifoli (Grifo).
An important center was fortified Montisi (formerly Monteghisi), originally relevancy of Scialenghi Cacciaconti. These while acknowledging the political dominoes Siena since 1175, continued to exercise their lordship over the castle until the end of the thirteenth century, not without controversy, even bloody, with the local communities. In the fourteenth century Montisi was made the appointment of a vicarage town, which has jurisdiction on nearby Castle Montelifré.Classico establishment of offshore fortified Montisi spread all over a hill whose summit is a Cassero significantly restructured. In identify two successive circles walls, the oldest of which, however, is very fragmented.
Belonging to Scialenghi also Montelifré Castle, which is known safe until after 1213, when the local community castle did act of submission to the town of Siena. Fortifications of Montelifré should have been destroyed in 1289, for resolution of the General Council of Siena, but perhaps not the measure had Corsican or castle was soon rebuilt. In time they would not stated established at the ancient castle of the possessions "nobil home Martinozzi Siena derived from a Martinozzo native Montepulciano that flourished on the principle of the 1300" (REPETTI). In 1526, after the battle of Camollia, the fortress was occupied Montelifré - like Grancia of Montisi - some sbandati.
On top of a hill, close to Montisi, are the ruins of the great fortress of Montelifré unfortunately being progressive disintegration, so that it is no longer possible to get an idea of where was the access or any other functional element, which show, part of the original coating to rows of limestone. At the foot of them, on the south-east, is the lower part of the castle, enclosed within a circuit of walls, leading to half a tower and which is a sort of row houses. The walls will encourage two-door opposed: one in the south-west antiporto and north-east, originally linked by a road, extraordinarily feature, which are still only about two-thirds, in fact, to the door of the northeast , was built a farmhouse that stops, forcing access to a side alley, so that the ancient port now only need access to the courtyard of the house above, while the entrance to the village has been moved more towards the fortress.

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