The Tuscan landscape at its most evocative – exposed rolling hills crossed by the ubiquitous ‘white roads’ and protected by dramatic hilltop villages, whose very stones reek of medieval power struggles and intrigue. And to assist in the consideration of these issues, two fine red wines, the rich Brunello di Montalcino and the Vino Nobile di Montepulciano, with their vineyards at the heart of our walk. From Siena, pass through Montalcino, the Abbey of Sant’ Antimo, Bagno Vignoni and its ancient thermal baths, historic Pienza and a final walk up from the church of San Biagio to the cathedral at Montepulciano. We recommend extra nights in most places to explore the treasures of these towns as well as to relax and to eat and drink well.