Dreaming of doing one of the classic Tuscany road trips to experience the Tuscan culture and landscape at your own pace? It’s telling that so many tourists come to see the same small valley south of Siena to leisurely drive the iconic countryside. Taking a Tuscany road trip is on many travelers’ bucket lists, a testament to its rare beauty. The patchwork of rolling wheat fields, verdant green forests and narrow cypress lined roads with earthy stone farmhouses dotting the quilt like buttons is just such a classic scene, and the perfect setting for a classic road trip in Italy. It's so iconic in fact, UNESCO (United Nations Educational, Scientific and Cultural Organization) has bestowed status not once, but seven times upon the region, including the swath of valley that defines the landscape of Tuscany — the Val d'Orcia.