How to reach
Montalcino can be easily reached from Siena by following the Cassia road (SS2) up to Buonconvento. After a few kilometers, you will find on the right a crossing road that leads to the town.
History
Montalcino rises in the heart of southern Tuscany. In the Middle Ages, the territory of Montalcino was divided into four ecclesiastical areas: Arezzo, Chiusi, Grosseto and Siena. This subdivision mirrored that of antiquity; in fact, here met the territories of the important Etruscan 'Lucumonies' of Arezzo, Chiusi, Roselle (Grosseto) and perhaps also of Volterra. Many recoveries from this time are today preserved in the Archaeological Museum of Montalcino.
The medieval history of this area is full of innumerable black holes, that's why the whole written documentation was preserved in the destroyed archives of the Abbey of S.Antimo, from which the castle depended. Also, the fact that the Francigena Road passed east of the town, near the settlement of Torrenieri, didn't help us retrieve historical notices preceding the second half of the 12th century.
The history that we know starts at the end of the 12th century, when the free town of Montalcino, allied with Siena during the war of 1176, lost, against Florence. Montalcino offered resistance to the expansionist aims of Siena, and the alliance was broken; consequently, in the mid-13th century, the castle was destroyed by the Senese army, momentarily in peace with that of the Florentine (busy to eliminate the analogous obstacle constituted by Semifonte). The renewal of hostilities with Florence prevented the Senesi from completing the conquest of Montalcino, but the castle remained under the protectorate of the Church and the Commune of Siena.
After a rebellion attempt to regain its autonomy, in 1232 the castle was reoccupied and forced into a new alliance with Siena. After another insurrection in 1252, the castle was conquered again by the Senesi but immediately lost due to the intervention of Florence and Grosseto. In the Montaperti battle Montalcino lined up with Florence against Siena, and the victory of this last battle didn't do anything else but bring the city to a new loss of autonomy. In 1269, Siena was again defeated at Colle Valdelsa and Montalcino was freed again. Only after half the 14th century did the castle return under the control of Siena. In this period, the fortifications were reconstructed to better control the city center.
By now, Montalcino was Senese, and in the 15th century, it became one of the most important centers of the Republic territory. In the following century, the city and the castle withstand, in 1553, the siege of the Medicean and Imperial armies during the war that brought Siena to the definitive capitulation of 1555. After the surrender, many citizens of Siena reached Montalcino, where, headed by Pietro Strozzi, they let the Republic live in exile. The city became the chief town of the territories not conquered by the Florentines and resisted until 1559, when, isolated by the fall of the castles of Talamone and Castiglione della Pescaia, offered its surrender and swore fidelity to Cosimo de' Medici.
The castle is practically intact today. Its construction began in 1361 on the southern vertex of the 13th century city walls, incorporating the keep of S.Martino and the S.Giovanni tower. It looks like a classic castle-enclosure, with a pentagonal plant endowed with towers from all angles. The tower of southeast is placed by the side of the keep. The walls and the towers have still practicably the complete watchwalk endowed with machicoulis (projection from the wall made of stone, which has openings through which the defenders can fire upon an enemy directly below) in stone, supported by bows on brackets with inverted pyramid form. The northern towers are open on the side facing the courtyard. The castle also incorporated an ancient little basilica that became the chapel of the fortification, and its remains are still visible near the northeast tower. On the south side rise the mighty Medicean rampart, added by Cosimo at the half of the 16th century.