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Ancient Benedictine monastic seat and capital of the Volterra Diocese, castle of the Della Gherardesca counts, and founded at the end of the XII century in the place of the pre-existing Church of St. Mary, Montescudaio enjoys a panorama from which the Cecina Valley plains are visible, as are all of the islands of the Tuscan archipelago right up to the mountains of Corsica.

The ancient name comes from the Latin 'Mons Scrutarum' that means Mount of the Shields: Montescudaio was in fact a fortified village of great strategic importance, given the dominating position on the area. Among the monuments to visit in Montescudaio particular mention should be made of the Church of St. Mary of the Assumption, the Guardian Tower and Villa Pucci. From the vineyards of the surrounding hills the excellent red wine Montescudaio DOC is produced.