Crete Senesi, Montepulciano and Cortona

Route description

Leave Siena south-east on the SP438, the Lauretana, which runs along the ridges of the Crete Senesi to Asciano. This landscape of bare grey clay hills, lone farmhouses and cypress lines is best at dawn or after rain in spring, when the wheat is green. From Asciano continue south to the abbey of Monte Oliveto Maggiore, hidden in a wood, and walk its frescoed cloister.

Drop to Buonconvento on the SR2 Cassia and climb to Montalcino, then take the road south to the abbey of Sant’Antimo, whose monks once sang Gregorian chant here. Return towards the Cassia and the Val d’Orcia to Bagno Vignoni, a hamlet built around a steaming pool. You cannot bathe in the square, but the warm streams below the village are free.

East of the Val d’Orcia, Montepulciano climbs a narrow ridge to its Piazza Grande; the wine cellars under the palaces sell Vino Nobile. Leave the car at the car parks outside the walls, as the old town is closed to traffic. At the foot of the hill, the church of San Biagio stands alone at the end of a cypress avenue, and has its own parking.

Cross into Umbria to Castiglione del Lago, a walled town on a promontory of Lake Trasimeno with a lakeside path and beaches. Finally head north to Cortona, an Etruscan town stacked up a steep hillside with views over the Val di Chiana. Its streets are very steep, so park at the lower car parks and use the escalators. Spring and autumn are the best seasons for this route.