The inland hills of southern Tuscany display the region at its best, an infinite gradation of trees and vineyards that encompasses the depopulated crete before climbing into the hills around Monte Amiata. Southwest of Siena towards the sea, the memorable but little-visited hill-town of Massa Marittima presides over a marshy coastal plain. Magnificent monastic architecture survives in the tranquil settings of San Galgano and, further east, Monte Oliveto Maggiore, which also boasts some marvellous frescoes. The finest of the hill-towns to the south of Siena is Montepulciano, with its superb wines and an ensemble of Renaissance architecture that rivals neighbouring Pienza.
Further south, the tourist crush is noticeably eased in smaller towns and villages that are often overlooked by visitors gorged on Florentine art and Sienese countryside. Wild Monte Amiata offers scenic mountain walks, while the isolated, dramatic medieval town of Pitigliano nurtures the amazing story – and scant remains – of what was once Tuscany’s strongest Jewish community.