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Montemassi, whose old town centre has retained the appearance of a compact hamlet at the foot of its gothic-style castle, has been made famous by the fresco portraying the castle during the assault lead by Guidoriccio da Fogliano in 1328. The fresco, attributed to Simone Martini, is preserved in the Palazzo Pubblico at Siena. The Sant’Andrea Apostolo Church, with some of its original furnishings still intact, is also well worth a visit. There are a couple of restaurant/pizzeria, one has a lovely view. During the summer the village hosts some open air events.
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