Meet your guide at the railway station in Siena to start the tour. Hop in an air-conditioned van to the hike to the starting point. The Via Francigena is an ancient pilgrimage route, first mentioned in records in the 8th century, that stretches from Canterbury in England all the way to the Vatican in Rome, going through France and Switzerland along the way.
While its popularity decreased with the rise of automobiles, the Via Francigena is regaining popularity as there are now regular hikers and pilgrims on the trail. Stroll along the path and notice the beauty around you: the rolling hills blanketed in olive groves and the occasional vineyard. Pass through ancient villages that look the same as they did centuries ago when pilgrims would stride past.
After about 2.5 hours of hiking, arrive at the striking village of Monteriggioni, a tiny walled town plopped atop of a medium-sized hill. Take part in a wine tasting here at a local wine shop and taste two different local varieties. After, feel free to explore the village at your leisure, popping into small shops, sitting down for lunch or investigating the medieval walls of the village. Your guide will give you a map that shows how to get to the railway station (a 30-minute walk) and, when you like, you can get the train back to Siena for the comfortable and scenic ride.