Montepulciano sits on a long limestone ridge at about 600 metres, overlooking the Val di Chiana to the east and the Val d'Orcia to the west, and it has the appearance of a town that has been polished by centuries of owners with taste. It is a Renaissance town, built largely by Florentine families and architects, with palaces such as the Palazzo Contucci and the Palazzo Comunale, and a main street, the Corso, that climbs in a long, steady slope toward the Piazza Grande at the top. The Duomo, the well and the town hall are here, and the view from the tower over the Tuscan hills is long.
The wine is the reason many people come. Vino Nobile di Montepulciano is a red made mostly from Sangiovese, known locally as Prugnolo Gentile, and it has been prized since the Middle Ages. The cellars are dug into the rock beneath the town, and many offer tastings. Do be sensible about drinking and riding, which are not compatible, and consider a spit bucket or a taxi. Pecorino cheese from nearby Pienza and pici, the thick hand-rolled pasta of this part of Tuscany, are the best things to eat.
The riding approach is lovely. The road climbs from the valley with views of cypress-lined drives, farmhouses and fields of wheat that go green in spring and golden in June. The surface is generally good, and the curves are gentle, but the roads are popular with cyclists, particularly in spring, and tourist traffic builds in summer. Go early and again late, when the light is low and soft, and the hills show their folds. Autumn, with the harvest and mist in the valleys, is a magical time.
Practical points: the old town is limited-traffic, so park outside the walls and walk up. Montepulciano has fuel stations on the approach roads and in the nearby villages, and plenty of cafes and restaurants inside. The town gets busy at midday, so a late afternoon arrival is easier. Stay for sunset, when the stone turns honey-coloured and the whole valley fades to blue.