The fortress of Montalcino, on a high level position (564 mt), has Etruscan origins and during the Middle Ages Siena and Firenze made it a matter of dispute and rivalled each other because of its strategic position between the Maremma and the internal valleys. Entered in the Sienese sphere of influence, after the battle of Montaperti, fought by the Sienese and the Florentine in 1260, Montalcino remained the last bastion of the Republic of Siena and was annexed to the grand duchy of Tuscany in 1559. Signs of military vocation in the area are the Fortress of 1300 and the slender tower of the municipal building, almost a lookout tower: the views and the foreshortenings between the alleys of the centre make Montalcino one of the most suggestive burghs of the whole Tuscany. In the splendid Civic and Diocesan Museum of Sacred Art in the ex St. Augustine convent, it is possible to admire paintings and sculptures of the Sienese school (Simone Martini, Ambrogio Lorenzetti, Francesco di Valdambrino). 9 Km away from Montalcino, following the direction Castelnuovo dell’Abate, rises the amazing Abbey of Sant’Antimo, Romanesque masterpiece of the XI century.