The Terre di Siena, as the countryside around Siena is known, are a stunning backdrop to the territory's artistic and cultural wonders, with dozens of roads to follow, each itinerary offering new ways of discovering Siena's natural beauty as you seek out its best known masterpieces.
The Crete Senesi is known for its soft hills and many consider it to be the most beautiful part of this region. Driving from Siena to Montalcino, the capital of Brunello wines, the views are unforgettable and stops at the Sacred Art Museum at Asciano and the stunning Abbey of Monteoliveto Maggiore are absolute musts.
The Val d'Orcia is the next stop, following the cypresses along a path that cuts the Terre di Siena from west to east and offers a natural panoramic viewpoint over one of Tuscany's most beautiful, and best known, corners. Heading from San Quirico d'Orcia towards Pienza, the "ideal" city born out of Renaissance humanism. Continue along your journey, stopping in Montepulciano for a visit to the cellars under the city and a taste of the local Nobile di Montepulciano, one of Tuscany's most prestigious wines. The Val d'Orcia itinerary continues with a visit to the spas at Chianciano Terme and ends at Chiusi, a fascinating city which hides an Etruscan past in its underground "Porsenna Labyrinth."
The Val d'Elsa is full of rich green woods and artistic masterpieces and is less visited than the neighbouring Val d'Orcia. Departing from Poggibonsi the first stop on the road is San Gimignano, the city of towers. Casole d'Elsa is the next stopover for a visit to the Collegiata di Santa Maria Assunta and the 14th-century fortress. This itinerary then ends toward Chiusino in the Val di Merse and the evocative Abbey of San Galgano.
For another perspective on the Terre di Siena follow the ancient Via Cassia which connected Siena with Rome. The road passes through Buonconvento, then Montalcino and Bagno Vignoni, with its beautiful water piazza and thermal springs. From here continue along to the foothills of the Amiata Mountain and stop at Bagni San Filippo, another thermal village where the waters spring from the earth at temperatures around 50° celsius.