Back to the route and at the 35 km point, the peloton enters the first unpaved section, which is also the longest (13.5 km, difficulty **). Then, after a brief return to smooth asphalt, the second section of white road ensues (5.5 km, difficulty *) with a light gradient, through woodland.
The other side of Buonconvento lies the climb at Montalcino, the hardest of the day (4 km, 5%). Beyond Torrenieri, sections 3 (11.9 km***) and 4 (8.0 km ****) are separated by barely a kilometer of asphalt. Both sections are hilly and demanding: the peloton gets twitchy here, among the curves and climbs.
After a second passage through Buonconvento, the race joins the main road, Strada Statale 3, for the feed zone (km 106-109). Then it’s the village of Asciano and, after 132.4 km, the fifth unpaved section. 11.5 km long and the hardest of the race at *****, Section 5 is mostly uphill, although it includes several undulations.