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Montemerano is part of the municipality of Manciano (Grosseto), about 10km northwest of the province capital. In the splendid hills of the Maremma area, it's situated between the beautiful landscape and scenic views along state highway SS322 (towards Scansano), at the junction with the SP10 (towards the spa town of Saturnia).
Like most medieval villages at the time, Montemaremo developed around a central castle on Montemerano hill, built by the Aldobrandeschi family in the 1200s. At the end of the 13th century, the Baschi family captured the town, and it became part of Ovietan domain at the beginning of the 1300s. After the decline of the Orvietan power in the 15th century, the Sienese gained control of Montemerano and turned it into an important fortress. With the final fall of the Sienese Republic in the second half of the 1500s, the village became part of the Grand Duchy of Tuscany and its incredible history.
Sitting atop a hill surrounded by olive trees, the historic city center's walls, towers, fortress, and several stone buildings dating back to the Middle Ages and the Renaissance have been conserved despite modern efforts make way for more profitable housing in the immediate surroundings.
The medieval walls of Montemerano, with batters (angled base walls) in blocks of limestone and travertine, enclose the entire village and are still easily discernable today. Erected in stages, and mostly rebuilt in the 1400s, they include the Cassero Senese stronghold, now an extremely modified square tower. To enter the village, one must pass through one of 2 doors: a low arch on the south side, or, facing north, a full arch inside a loggia opening onto "Church Square." The section lining the western part of town, built in the Renaissance, has two square and two circular towers. The northeastern side is equipped with a wall-walk.
San Giorgio Church, overlooking Piazza della Chiesa (Church Square), was built in the late middle ages. It was expanded in the first half of the fifteenth century, when the apse and transept were added. The church houses works of art from the Renaissance Age, including murals, tables, and vestments. The most striking piece is a recently restored polyptych (panel painting) by Sano di Pietro from the 1400s, featuring an enthroned Madonna with Child and saints. Another 15th century painting, La Madonna della Gattaiola (roughly translated to, "Madonna of the Cat Door"), gets its name from the clear presence of a hole (for the passage of cats) in the door on which it's painted.
La Torre di San Lorenzo era originariamente adibita a campanile dell'omonima chiesa di origini medievali, successivamente dismessa e adibita a residenza privata. Attualmente si presenta, purtroppo, con la brutta intonacatura imposta dalla Sovrintendenza ai beni artistici e culturali di Siena e Grosseto.
Il vero gioiello di Montemerano è la spettacolare e scenografica Piazza del Castello, intatta nel suo assetto medievale e nelle case di pietra. Vi si accede attraverso una porta ad arco che si apre al termine di una breve via in ripida salita. A sud-ovest di Montemerano, fuori dal centro abitato, sorge nella campagna la quattrocentesca Chiesa della Madonna del Cavalluzzo.