The evocative scenery of Tuscany—rolling hills dotted with stone farmhouses and towering cypresses—make the region a favorite destination for travelers on our private Italy tours.

The epitome of this breathtaking Tuscan landscape is the Val d’Orcia, an agricultural region outside Siena that has changed little since the Renaissance. The Val d’Orcia is now recognized as a UNESCO World Heritage Site for its beautiful scenery (due in part to Renaissance-era land management), historical villages and the infrastructure built along the ancient Via Francigena pilgrimage route.

During the 14th and 15th centuries, utopian Renaissance ideas and the mercantile wealth of Siena transformed the Val d’Orcia into a kind of giant landscape garden. Landowners sought to maintain productive farmland while also enhancing the natural scenery, making it more aesthetically pleasing by carving winding roads into the hills, planting vineyards and trees, and cultivating fields of sunflowers and wheat that turn golden in the summer.

The rows of cypress trees that punctuate Tuscan landscapes serve both practical and aesthetic purposes. The tall, dense trees were planted as windbreaks along roads and near buildings. But their striking vertical forms were also deliberately arranged to add visual interest to the landscapes according to Renaissance ideals of beauty.

Travelers on the Via Francigena pilgrimage route between Canterbury and Rome crossed through the Val d’Orcia, increasing demand for bridges, inns, abbeys and other infrastructure in the region over the centuries.

The resulting patchwork of farms and villages was immortalized as the ideal Tuscan landscape by Renaissance artists and writers, an image that continues to resonate with many visitors to the Val d’Orcia today.

In addition to stunning landscapes, the Val d’Orcia is a rich repository of art and architecture, such as the UNESCO-inscribed Renaissance town of Pienza, the fresco cycles of Abbazia di Monte Oliveto Maggiore and the charming Chapel of the Madonna di Vitaleta.

The Val d’Orcia also offers incredible private Italian food and wine experiences, such as visiting a pecorino cheese dairy, sampling olive oil at an olive mill, and tasting prestigious wines such as Brunello di Montalcino and Vino Nobile di Montepulciano at top local wineries.

We take our travelers to the most scenic parts of Tuscany, including Chianti, Siena, Pienza, San Quirico d’Orcia, Montalcino and Montepulciano. Other favorite experiences we arrange in the Tuscan countryside include guided hikes in the rolling landscapes, private art touring, truffle hunting, visits to formal Italian gardens and ancient abbeys…

…private cooking classes and reservations for memorable meals at our favorite restaurants. In July and August, we can arrange VIP attendance at the Palio di Siena, the historic horse race in the Piazza del Campo in Siena.

Many of our travelers combine time in Tuscany with private city touring in Florence, Rome and other favorite destinations in Italy.

For travelers short on time, we can also arrange private day excursions from Florence to either the Val d’Orcia or the nearby Chianti countryside.

Contact an Artisans of Leisure Italy travel specialist to begin planning a luxury Italy tour featuring the highlights of Tuscany.