The stronghold of Montalcino, in an elevated position (metres564), has Etruscan origins and during the medieval period was long fought over by Siena and Florence for its strategic position between the Maremma and the inland valleys.
Entering Siena's sphere of influence after the Battle of Montaperti fought between the Sienese and Florentines in 1260, Montalcino was to be the last bastion of the Republic of Siena and was annexed to the Grand Duchy of Tuscany in 1559.
Signs of the place's military vocation are the 14th-century Rocca (fortress) and the slender tower of the Palazzo Civico, almost a lookout tower: the views and glimpses among the narrow streets of the centre make Montalcino one of the most evocative villages in all of Tuscany.
In the beautiful Civic and Diocesan Museum of Sacred Art in the former Convent of Sant'Agostino, one can admire works of sculpture and painting from the Sienese school (Simone Martini, Ambrogio Lorenzetti, Francesco di Valdambrino).
9 km from Montalcino, in the direction of Castelnuovo dell'Abate, stands the beautiful Sant'Antimo Abbey, an 11th-century Romanesque masterpiece.