Arrive at the base of Civita di Bagnoregio, an ancient village perched on a crumbling volcanic plateau. Cross the dramatic pedestrian bridge that connects this isolated town to the modern world, with sweeping valley views on both sides.

Next, head into the Montepulciano countryside to visit a family-run winery. To start, sample typical local products such as pecorino, prosciutto, salame, capocollo, and bruschetta with olive oil. If time allows, you may also have the chance to explore the small cellar museum. After the tasting, sit down for a warm, rustic meal featuring handmade pici pasta with traditional aglione sauce. Pair lunch with three wines, then finish with cantucci and Vin Santo.

Continue to Pienza for 1.5 hours of free time in this Renaissance hill town. Walk the honey-colored streets, browse local food shops, and take in broad Val d’Orcia views that look like a painted landscape.