Montepulciano is Courteous but Reserved...

Montepulciano is not exactly undiscovered, but it's below the radar enough and big enough (with a population of almost 15,000) to absorb its visitors gracefully, without becoming a tourist souk. 

Standing imperious on its high tufa ridge, Montepulciano seems to have been positioned by a landscape painter and laid out by a designer of Renaissance opera sets. It has one of the most intact and architecturally unified historic centres of any Italian town: within its walls, apart from a few nips and tucks, no major building work has taken place since 1580. It has some good restaurants serving hearty southern Tuscan fare, one or two rustically elegant places to stay, and it makes one of Tuscany's most serious, full-bodied red wines. But the town also has a certain reticence about it, a private side to its character. Because if a Tuscan town is too easy, too eager to be liked, it's not properly Tuscan. 

Just like the locals, Montepulciano is courteous but reserved. Indeed in winter, or under a louring grey sky, it can even feel a little dour: along the Corso, the main street that winds up to scenographic Piazza Grande at the town's summit and centre, tall green-shuttered medieval houses rise like cliffs on either side, and the piazza itself – big as a football pitch, surrounded by solemn Renaissance palazzos, the crenellated Gothic town hall and the rough, unfinished brick façade of the Duomo – can feel beautiful and unsettling at the same time. 

What saves Montepulciano from medieval introspection is its rapport with the land and its produce. From the panoramic terrace outside the church of San Francesco, the view stretches west across neat vineyards and patchwork fields of corn and sunflowers to distant wooded hills. 

While Montepulciano may not be able to compete with Siena or Pisa in terms of art and architecture, it has enough to reward the patient visitor. In the Middle Ages and early Renaissance the poliziani, as the town's citizens are known, put most of their energy and patronage into civic hubs like Piazza Grande and the embellishment of churches. 

There are some lovely artworks in the latter – my favourite being two early Madonnas, the first a 14th-century fresco fragment in Sant'Agnese showing the Virgin breast-feeding the infant Christ, the second the so-called Madonna of the Pillar in the Duomo, by Sano di Pietro: a tiny, exquisite panel painting of a trustful Mary nestling her head into the prettiest redhead Jesus, chubby-cheeked and wide- eyed, clutching a little bird, perhaps a goldfinch. 

Following Montepulciano's alliance with Florence in 1511, the town was given a facelift by its new Medici overlords. Two of Italy's leading architects, Vignola and Antonio da Sangallo the Elder, were brought in to spruce up family palazzos and give civic spaces and edifices a more imposing look. 

It was Sangallo who left the most enduring mark – in the church of San Biagio, which stands like a marble vision below the walls to the west of town. Made of white travertine that takes on a golden hue in the evening sun, this beautifully proportioned Renaissance hymn to the classical orders and the theory of the Golden Mean would look a little too studied in a city setting: but surrounded and softened by the vineyards and oak forests of this painterly corner of southern Tuscany, it's simply stunning.