Most of those for whom Montalcino is famous know it for its wines (Brunello, Rosso…), which however are substantially recent “invention” (mid 19th century); moreover, much less than for wine and almost only in Italy - indeed in Tuscany - the town is known for being the last "bulwark of Sienese freedom"; that is the place where, after the fall of the republic of Siena under the dominion of Duke Cosimo I Medici (shortly thereafter: Grand Duke) in 1555, the Franco-Sienese army commanded by Filippo Strozzi withdrew, resisting to the bitter end; this resistance ended only with the peace treaty of Cateau-Cambrésis (1559) which sanctioned the end of the wars (waged on several European fronts) between France and Habsburg (Spain-Austria).
There is a substantial reason why the resistance of the Franco-Sienese army centered on Montalcino, a reason that appears from the features of the historic center of Montalcino itself: the importance of it. To today's visitor, Montalcino could appear to be a “miniature” medieval city. But it is such only if it is commensurate with other Tuscan cities of medieval origin; transposed to more peripheral areas of Europe at the same time, it would be considered just "an important city".
Historians, in particular Maria Ginatempo and Lucia Sandri, "La terra delle città" (1990), help us to understand the context of Montalcino. Around the year 1300, Tuscany is the region with the highest percentage of urban population in Europe (over 25%). At the top of the urban pyramid there is one of the European metropolises (Florence is surpassed only by Paris and Milan, and approximately equal to Venice and Genoa), then there are two of the twenty largest cities in Europe (Siena and Pisa) and finally one dense array of centers whose population does not impress us today, but it is considerable if we think that (for example) London at that time had perhaps 40,000 inhabitants.
In this context, Montalcino already at the beginning of the thirteenth century has 3500 inhabitants, almost 2/3 of those of today, and it's therefore an entity anything but negligible, because - it seems - above all of the flourishing industry of tanneries (today of all disappeared). Probably at the time the inhabitants of Montalcino were equal to those of nearby Montepulciano (which, however, appears more impressive today, since its importance has continued in the following centuries). The built form of Montalcino is the consequence of this relative primacy: it's enclosed within walls 4 km long (built in the 13th century), dotted with churches and convents, with the tall and narrow "Palazzo dei Priori", seat of urban power, which more or less occupies the center of the settlement. The whole is dominated by the fortress built by the Sienese when they took possession of the city (mid-fourteenth century).
Above all, Montalcino is the last entity that in the late Middle Ages can be called "town", if one proceeds from the economic heart of Tuscany towards the south-west, the depopulated and unhealthy Maremma. From here to the Tyrrhenian Sea the only other city is Massa Marittima, for well-known reasons: it's one of the most typical "mining republics" in Europe. For the rest there is the "urban desert". Montalcino therefore also suggests an image of "finis terrae" that is well suited to its role in 1555-1559 war, mentioned above.