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Casole d'Elsa has always formed a bulwark for the Sienese in a border area strenuously defended against the people of Volterra and Florence owing to its strategical position in the upper Elsa Valley, and it still has the air of a final outpost.
Romantic traces of fortifications emerge in several places, and noble houses gradually adapted to the needs of man. One example is the Romanesque convent of the Servites, right at the entrance to the village, and another the 14th-century palace of the old feudal lords of Casole, the Porrinas, who were later ousted by the Sienese Republic. Most fascinating of all is the splendid Collegiate Church of Santa Maria Assunta, almost all in brickwork, consacrated in 1161 on the remains of a previously existing building and continuously transformed and touched-up ever since. In the interior, amongst other important items, one can admire works by Rutilio Manetti, Marco Romano and Gano da Siena. There are also fine paintings (Bernardino Mei, Girolamo del Pacchia) hanging in the Sacred Art Museum in the nearby Canon's house. Still immersed in the Middle Ages, one can admire the Praetorial Court with its carved coats-of-arms, and then the great Fortress dating back to 1352 (nowadays the seat of the Town Hall), reinforced by two unequal towers. The powerful walls encircling the village are still mostly intact and include two circular towers designed by the great Sienese architect Francesco di Giorgio.
Visits worth making round about Casole d'Elsa are to the villages of Mensano (once a mighty castle destroyed by the Florentines in 1534) with the fine 11th-century Church of San Giovanni, and Pievescola, with its remarkable Romanesque church with a nave and two aisles.
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