The castle on the hill overlooking the tiny village of Montemassi north of Grosetto, built by the Aldobrandeschi family around 1000 AD and almost constantly besieged by Siena, who could not, ever, control the rebellious locals, who refused to be ruled by anyone until the 17th century, when things were relatively harmonious under the feudal lord of nearby Roccatederighi.

A few kilometers away, little Roccastrada was just as proud. Conquered and ruled by Siena because of its nearby copper and silver mines, in the late 19th century a long strike action by local doctors (yes, doctors) replaced the ruling lords with an independent republic. In the early 1900’s legal action won them tilling rights to their lands, then they got rid of the clergy and supported the feminist movement. After the first world war they elected Italy’s first socialist mayor who enacted sweeping reforms, and the fascists got so fed up with them by 1921 that they massacred innocent townspeople in frustration. Not done, the town was home to the Gransci Brigade of partisans who battled the nazis throughout the second world war as well.