The hill towns and valleys south of Siena comprise perhaps Tuscany's most enchanting and downright picturesque region. It's a land of medieval castles guarding narrow road passes, isolated farmhouses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a bucolic backdrop, and thermal spas enjoyed by both the Medici and the modern proletariat. The region has a few small patches of forest on the steeper slopes of its river valleys, but most of it has been landscaped to a human scale over thousands of years, turning the low, rolling hills into farmlands and vineyards that produce Tuscany's mightiest red wines.
Southern Tuscany's cities are textbook Italian hill towns. Chiusi dwells deep in its Etruscan roots, still remembering a time when King Lars Porsena was one of the few leaders of the Etruscan confederation who had the audacity to take on Rome. Roman settlements like Montalcino and Montepulciano grew into medieval cities and today produce two of Italy's top red wines, the powerhouse Brunello di Montalcino and the noble Vino Nobile di Montepulciano. And the gemlike village of Pienza, famed for its pecorino sheep's cheese, shelters within its tiny ring of walls a Renaissance core of the most perfect proportions and planning.
Much of the area is filled with the expansive and beautiful Val d'Orcia -- many people's idealized picture of Tuscany because well over half the souvenir-stand postcards and cover shots of coffee-table books with "Tuscany" in the title were snapped here. From many parts of it, especially the zone around Montalcino and Pienza, you can see the broken tooth of the Rocca d'Orcia. From the 11th to the 14th century, the castle was a stronghold and strategic watchtower of the Aldobrandeschi clan, formidable toll collectors along the Francigena pilgrim road through these parts. The castle juts from its crag to the south, still keeping an eye on its valley.
