Compared with the medieval castles in Valdambra, Cennina has preserved best its original character. The ancient fortress was foundet on the remains of Etruscian and Roman ruins. Those have been postgards of the roads which connected the Chianti area to the “Cassia Adrianea”, important road in the near valley.

The today visible fortrees was built in 1167 by the Ghibelline count Alberico d`Uguccione Brandaglia. As usual during this feudal period, the Castello di Cennina changed owners several times. Because of its strategic position, Cennina was object of furious contentions between Siena, Arezzo and Florence, whose borders all met in the Ambra valley. 1336 the castello was placed under the protection of Florence. In the same year the Ubertini took over Cennina, Florence sent troops commanded by Albertaccio Ricasoli and Giovanni Alberti. The Ubertini were forced to admit the troops. Cennina changed owner again. 1360 the Castello was included into the “Lega della Valdambra”. This military organisation was followed five years later by an administrative one, that divided Valdambra into three “terzieri”. When 1388 the war between Siena and Florence started again, Cennina became part of Siena. It was conquered again in 1447 by Aragonese troops.

By the grand Duke Leopold`s reform in 1173, Cennnina was included in the community of Bucine, where it remains until today. With the abandonment of the countryside after the Second World War, also Cennina gradually lost its popolution. But since several years the opposite tendency can be noticed. A social society has turned Cennina into a center of culture. Conferences, concerts, plays and exhibitions of high culture level take place. The Castello di Cennina was waken again and today, is integral part of culture life in Toscana. For its historical and architectural value, the whole hill of Cennina is under the protection of the “Soprintendenza ai Beni Culturali ed Ambientali”, an Italian ministry.