From Sinalunga, the route first crosses the Val di Chiana: flat roads, fields, scattered houses and a short passage through Foiano della Chiana. Until Castiglion Fiorentino, the day stays open and fairly direct. Then the route changes clearly. The GPX leaves the plain, climbs between houses and stone walls, and continues into woodland and drier hillsides. Around Palazzo del Pero, it reaches the highest part of the stage, then stays rolling all the way to Anghiari. The town does not sit conveniently in the valley; it waits uphill, with walls, stone and steep lanes.