Highest of all the major Tuscan hill-towns, at more than 600m, the ravishing, self-contained community of MONTEPULCIANO stretches atop a long, narrow ridge 65km southeast of Siena. Its main street, the Corso, coils its way between scores of crumbling Renaissance palazzi and churches, here clustered around perfect little squares, there towering over tiny alleyways. Wherever stairways or mysterious passages drop down the hillside, you get sudden, stunning glimpses of the quintessential wine-growing countryside rolling off to the horizon; occasionally terraced gardens allow you to contemplate the whole stunning prospect at leisure.
Henry James, who compared Montepulciano to a ship, spent most of his time here drinking – a sound policy, in view of the much-celebrated Vino Nobile, production of which dates back well over a thousand years.
Montepulciano’s rise to eminence began in 1511, when the town finally threw in its lot with Florence rather than Siena. The Florentines thereupon sent Antonio Sangallo the Elder to rebuild the town’s gates and walls, which he did so impressively that the council took him on to work on the town hall and a series of churches. The local nobles meanwhile hired Sangallo, his nephew Antonio Sangallo the Younger, and later the Modena-born Vignola, a founding figure of Baroque, to work on their own palazzi. Totally assured in conception and execution, this trio’s work makes a fascinating comparison with Rossellino’s Pienza.