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.

Book through Rough Guides’ trusted travel partners

Italy features

The latest articles, galleries, quizzes and videos.

20 picturesque Christmas destinations

20 picturesque Christmas destinations

Dreaming of a trip this Christmas? We're here to help. From glittering cities to a few snowy escapes, here are 20 classic destinations for a festive break. …

12 Dec 2017 • Rough Guides Editors camera_alt Gallery
Discovering Palermo: why you should give Sicily’s capital a chance

Discovering Palermo: why you should give Sicily’s capital a chance

A city of grit and forgotten grandeur, for too long Palermo has resigned itself to being a film set of crumbling palaces, sun-worn facades and pockmarked backst…

08 Dec 2017 • Olivia Rawes insert_drive_file Article
19 places to get utterly lost

19 places to get utterly lost

One of the great joys of travelling is stumbling across unexpected places, wandering without a single destination in mind and embracing the journey. These place…

12 Sep 2017 • Keith Drew camera_alt Gallery
View more featureschevron_right