Set your GPS: Siena, Radi, Murlo, Bibbiano, Castiglion del Bosco, Montalcino, Torrenieri, Cosona, Pienza, Monticchiello, La Foce, Castiglioncello del Trinoro, Sarteano, Radicofani, Ponte del Rigo, Celle sul Rigo, San Cascano dei Bagni
The key for leaving Piazza del Campo is the SR2 Cassia in the direction of Rome. A few kilometers and then there's a steep descent; turn to the right and take the dirt road. There's a sign that says Eroica, where they hold the famous vintage bike race on mixed terrain. The road is not difficult, even for beginners, and the views are amazing, especially those of Fattoria di Radi and the Vescovado di Murlo.
There are both paved and dirt roads all the way to Castiglion del Bosco. We pass the golf course belonging to Ferragamo. If the view of the vineyards and oaks make you thirsty for a glass of Brunello, the emperor of wines, so take a break at the Enoteca della Fortezza. Montalcino has the perfect view of the Artistic and Natural Park of the Val d'Orcia, a Unesco heritage site and paradise where Nirvana can be found.
Heading down SP45 towards Brunello in Valdicava, the road takes a few curves and then leaves you with a great view all the way to Torrenieri, the old hitching post. The Pieve di Sant'Anna in Camprena allows you to see the frescoes of Sodom, an artistic preamble to the papacy of Pienza. Sacred and profane are easily mixed here and now ... it's time for another break, enjoying one of the many kinds of Pecorino. Enjoy them all. Take the dirt road towards Monticchiello, a medieval town where each summer there's a theater festival hosted right in the streets.
Swerving between the cypress trees that flank the most photographed road in the world is fun, but be sure to stop in Castelluccio and visit the La Foce vineyard belonging to the Marchesi Origo. This family gave life to the Val d'Orcia in the beginning of the twentieth century and chased away the Germans in the Second World War. Don't miss Sarteano, with its Giostra del Saracino in August, which you can get to from Castiglioncello del Trinoro.
The Rocca di Radicofani stands out and indicates the place where the brigand Ghino di Tacco worked his mischief and tells us we are at the border. A little bit more valley and then the shady Monte Amiata is just a hop away. There are a few nice curves between here and San Casciano dei Bagni; put down the kickstand and if you are there in August, enjoy the Frog Race.