Deep in an unspoilt, dreamy countryside, studded with soft heaving hills, there’s a winding road lined with cypress trees. This is probably the image that best represents Tuscany and its landscapes. If you follow the ancient Via Cassia, going south from Siena, you’ll find one of the most charming and characteristic views of the region: the Val d’Orcia, a UNESCO heritage site.As soon as you enter this enchanting valley, a unique and evocative territory opens up before you: vines, olive trees, fields and woods forming a lovely patchwork, with villages filled with outstanding art and architecture, like Montalcino, San Quirico d’Orcia, Pienza and Bagno Vignoni, to name the most popular. But there’s more to discover: for example, not far from Pienza, there’s also a lovely medieval village called Montichiello surrounded by fascinating scenery.