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 perching atop limestone ridges, stands of cypress and ribbons of plane trees against a bucolic backdrop, and thermal spas enjoyed by both the Medici and modern health-seekers. The minute you hit the dramatically scarred Crete Senesi hills just beyond Siena, the savage beauty of this region becomes apparent. A few small patches of forest stick to the steeper slopes of its river valleys, but most of it has been landscaped to a human scale over thousands of years, turning the 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 Porsenna was one of the few leaders of the Etruscan confederation who had the audacity to take on Rome. Sarteano has unique Etruscan frescoes that predate the Renaissance by millennia. 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 subtle 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 occupied by the Val d'Orcia -- an expansive valley that glows a bright emerald green in spring, and burns to golden-brown under the fierce summer sun. Souvenir-stand postcards and cover shots of coffee-table books are snapped right here.