Outside and inside the walls and the imposing Fortress of Montalcino, numerous armies and leagues of soldiers, Sienese, Florentine, French, Spanish and more have passed through, led by brave men-at-arms such as Giordano Orsini, Don Garcia de Toledo, Andrea Spagni, Panfilo dell’Oca, Mario Sforza, Giulio Vieri, Piero Strozzi and Blaise de Monluc.
Whether enemy or foe, these distinguished characters are among the era’s most famous protagonists in the art of war, and their acts of bravery spanned five centuries of long brutal sieges. Montalcino was seen as a strategic “piazza” stronghold for its dominating position at 564 meters above sea level, with views ranging from Val d’Orcia to Casentino, Monte Amiata to Maremma, and from Siena to the Tuscan-Emilian Apennines.
An ongoing war between the Ghibelline Siena and the Guelph Florence saw the two powers alternately lay claim to rule the city during the 13th century. The noteworthy battle of Montaperti “which turned Arbia red” in 1260, is how Dante recalled it in the Divine Comedy. In the 14th century, the inhabitants of Montalcino, including the elderly, clergy, women, and children, joined the armed soldiers in the Sienese Republic’s battles. According to historical documents from the period, the citizens were never caught off guard by assaults. They repaired the fortress walls at night, and they never went a day without “delicious bread and excellent wine”.
Montalcino came to represent a second home for the Sienese after their defeat at the Siena war. The French Emperor called war on the Spanish emperor, Charles V and the Pope. After the victorious defense of Montalcino from the Imperial and Medici militias in 1553, and the defeat and surrender of Siena in 1555, the Sienese exiles withdrew to Montalcino, a refuge on which they founded the Republic of Siena, and even minted coins.
Montalcino was also the last bastion to pass into Cosimo I de Medici’s hands, on 4 August 1559 with the peace treaty Cateau-Cambrésis between France and Spain, but never fell under their arms. Feeding the legend of a city that, looking at its interests and autonomy, will never be conquered.