Should you prefer castles then you have to look for Castello di Bibbione, erected before the year 1000 and restored in the XI century; in the Sixteenth century it was a property of the Machiavelli family who made it their hunting residence until 1727. Another amazing castle is certainly Castello di Gabbiano, with its rounded towers and its crenellated perimetral walls, built by the Bardi family during the course of the XIII century.
Just 3 km away from San Casciano Val di Pesa, stands the little village of S. Andrea in Percussina, that aside from maintaining its original aspect throughout the centuries it is famous also for having been the residence of Niccolò Machiavelli at the time of his exile. The farm, with its tavern named the Albergaccio is described in one of the most famous letters written by Machiavelli and right here, in his library, the Florentine author wrote The Prince, the work which would give him his present fame. After his death, the house passed to his heirs, now it belongs to the leading Italian wine group Gruppo Italiano Vini who restored it thoroughly. The rooms, the cellars and the tavern are still immersed in their ancient, unique atmosphere.
In 2009, in San Casciano were shot several scenes from the tv serie The Monster of Florence – broadcasted in the same year by Fox Crime. In the countryside of San Casciano Val di Pesa took place the last homicide committed by the perpetrator (or the perpetrators)
P.S. The best thing you can do to discover the town and its surroundings, is to rent a car and organize your favourite tour. There are several car rental companies you can contact of course, but Blucar Service is definitely one of the top ones in Tuscany.