The passage to the Roman era is documented on the contrary with scarce findings: the only significant fact is the administrative division operated by the Romans between the municipalities of Fiesole, Arezzo and in the Augustan age of Siena. The Lombard period is known to us for the long disputes between the bishops of Siena and Arezzo for the partition of the territory: in 715 King Liutprando tried to resolve the dispute. In the early Middle Ages it is therefore possible to trace a summary division of the territory between the feudal lords and the religious of the great abbeys of Passignano, Montemurlo and Coltibuono, a balanced division between temporal and spiritual power.In the tenth century the Chianti appeared divided into various fiefs by the Marquises of Tuscany, which as imperial vicars had jurisdiction. The central power was at that time rather weak and only in the case of great personalities, like the Marquis Ugo, it was felt. Most of the time it was the lord of the place who ruled his fiefdom from his castle as an absolute sovereign. But we must not think of extreme situations: in the Middle Ages there were never, as during the Roman period, revolts of slaves and peasants. The fiefdom was organized as a closed system, a large family: the peasants had to give part of the harvest to the lord, but this offered him protection and protection in case of raids and assaults from the outside. In this period the region is dotted with a myriad of castles, mostly located on hills in militarily strategic positions. The families of the Longobard and Frankish nobility have often remained proprietary until today of great estates who, with a touch of snobbish pride, have never abandoned, devoting themselves to the care of the territory: deeply linked to their land, they often see themselves moving among the rows of their properties, more interested in wine than in worldly salons. In the dispute between Arezzo and Siena, in the twelfth century also included Florence, aware of its economic and political power in continuous ascent, did not see favorably the proximity of a dangerous rival such as Siena. Thus the Chianti became the battlefield between the two cities. The struggle for the possession of Chianti can be said ended at the beginning of the thirteenth century: with the peace of Fonterutoli of 1201 and the Lodo di Poggibonsi of two years later, the Florentine Republic annexed all that territory which from now on will be called Chianti. The border between the two republics therefore remained for centuries very moved to the south and two fortified lines were created, a sort of iron curtain of the time: on the Florentine side it was made up of the castles of Brolio, Cacchiano, Monteluco, Montecastelli, Montemarchi , Rentennano and Tornano that faced each other with those of Siena, Aiola, Civitamura, Cerreto, Selvole and Sesta.