Montalcino is mentioned for the first time in a document of AD 814 in which Charlemagne’s son Louis the Pious granted this territory as a feudal domain to Apollinare, abbot of Sant’Antimo.
One of the names used to refer to Montalcino in its earliest times is Mons Ilcinus, which means “mount of the ilexes,” because of the trees that originally covered the hill before human settlers planted grapevines and olive, chestnut, and fruit trees there; the ilex tree remains the town’s emblem on its coat of arms. In the tenth century, probably as a result of barbarian invasions from the north, a real wave of migration from neighboring areas converged on the highest part of the Montalcino hill to settle there permanently.
The first cores of settlement arose then, around the church of Sant’Angelo in Castelvecchio, which was later replaced in the thirteenth century by the church of San Francesco with its adjacent convent; Sant’Egidio, dating to the eleventh century and destroyed in the 1300s to build the fort; and the Pieve (baptismal church) of Santissimo Salvatore, built around the year 1000 and destined to become the cathedral. In 1100, walls were built around the town, more than 4 kilometers long, with six gates and thirteen watch towers.
In 1191 Montalcino was already a free commune; in 1235 the podestà (chief administrative official) was Jacobo di Schiatta degli Uberti, the father of Farinata degli Uberti, a famous figure in Dante’s Divine Comedy.
From the thirteenth to the mid-fourteenth century, Montalcino’s territory was at the center of wars between the Sienese and the Florentines who fought to dominate it, while the abbey of Sant’Antimo was determined to exercise its own feudal rights. In 1361 Montalcino was captured by the Ghibellines and became a part of the Republic of Siena, at the time going through great political conflicts, which Saint Catherine (1347-1380) and later Saint Bernardino (1380-1440) made efforts to resolve peacefully.
Thus during the Middle Ages the structure of the Montalcino we see today was taking shape, with the principal churches that still exist: Santa Maria del Soccorso, Sant’Agostino, Sant’Egidio, and Santa Maria delle Grazie; this last church was known from the fourteenth century, when it appears as one of the possessions of the abbey of Sant’Antimo. In the fifteenth century the convent of the Williamite nuns was built.
The Sienese pope Pius II raised Montalcino to the rank of a city and then made the ancient baptismal church of the Santissimo Salvatore the cathedral, establishing the united diocese of Montalcino and Pienza, his home town. The bishop resided for the most part in the Renaissance city of Pienza, until in 1528 the two dioceses were divided, then reunited, and finally separated definitively in 1599.
Montalcino was the birthplace of many illustrious historical figures, such as Bernardo Lapino, a learned humanist and commentator on Petrarch as well as a friend of Enea Silvio Piccolomini, Pius II, who came here often to pay him a visit, strolling through the spaces of the Franciscan convent.
The church of San Lorenzo in San Pietro dates from the time of Pius II, but it was heavily remodeled in the eighteenth century. It housed the company of flagellants called the Compagnia dei Disciplinati di San Pietro, known for their strong spirit of charity and devotion. The church of Sant’Antonio Abate also dates to the mid-fifteenth century; the façade and interior, which houses a painting from the second half of the sixteenth century showing the Crucifixion with Our Lady and Saints John the Evangelist, Anthony Abbot and a Bishop Saint, and an early seventeenth-century Death of Saint Anthony Abbot by the Sienese painter
Pietro Sorri, were remodeled in the eighteenth century.
When the Republic of Siena fell in 1555, Montalcino held out for four years against the siege of the Spanish troops allied with the Grand Duke of Tuscany Cosimo de’ Medici. It was the last free commune in Italy, until it fell under Medici dominion in 1559.