The hill towns and valleys south of Siena comprise perhaps Tuscany`s most captivating and picturesque region, much of the area is filled with the expansive and beautiful Val d'Orcia (most people`s idealized picture of Tuscany). It is 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 rural setting, and thermal spas dating from long times past. Most of the region has been landscaped 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. This is Etruscan country, where the necropolis near Sovana hints at a rich and somewhat mysterious pre-Roman civilization, where 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 where the gemlike village of Pienza shelters within its tiny ring of walls a Renaissance core of the most perfect proportions and planning.