This is a full-day excursion from Siena to the Val, d’Orcia, a UNESCO world heritage site with beautiful nature, picturesque hilltop towns and world-renowned vineyards. Traveling by private car and in the company of a local expert in history, art, and culture, this tour covers both the artistic and gastronomic highlights of the area. Tour Medieval and Renaissance hill towns, experience wine tasting at a Brunello di Montalcino winery and enjoy locally produced cheeses, all while taking in spectacular panoramas along the way.  

You will travel together with your guide by private van to get off the beaten path and into the heart of one of the most scenic areas of central Italy. On your drive, you will learn about the origins of the region - a UNESCO World Heritage site since 2004 - and the nearby Via Francigena. You will stop and visit Pienza, a renaissance gem of urban planning and city design whose classical origins inspired the template of cities all over Italy and, by extension, the world. While exploring the charming town, you will sample delicious locally produced sheep's milk or pecorino cheeses.  

Afterward, you will travel through the stunning countryside to Montalcino, a medieval village of ancient origins. Surrounded by fortified walls, this tiny stronghold was once a leather-making center of Tuscany and is now most famous for the vineyards beyond its borders. After a walk around the town center, you will sit down for a local lunch in a trattoria with your guide.  

After lunch, you will make your way to the Abbey of Sant’Antimo, a twelfth-century Benedictine monastery with eighth-century roots. In the peaceful surrounds of the Tuscan hills, your guide will unfold this chapter of Italian history for us. You will complete your day with a visit to a local winery to see the operation and have a tasting while learning about the classification of Italian wines and understand the climatic conditions necessary to produce the Sangiovese grapes integral to Brunello wines.