Monteriggioni-Siena-Castello di Brolio-Vagliagli-Monteriggioni

From Monteriggioni, you reach Badesse, then via a provincial road, Il Beccio. A short stretch along Cassa Nord until Fontebecci, where we take Via Fiorentina that leads us to Porta Camollia, at the gates of the center of Siena. The route arrives at Piazza del Campo with a wide detour due to one-way streets, but from Porta Camollia, with a bit of attention, one can cross the center (of course with the bike in hand in the busiest sections). We leave Siena through Porta Romana and take a left on Strada della Certosa, a beautiful panoramic road that, unfortunately, we leave soon to head to the road of Pieve a Bozzone. We follow it for about 5 km until we turn left onto the road of Montechiaro that leads us to the outskirts of San Giovanni a Cerreto. We turn right and reach Pianella, continue for a little over 1 km on SP di Montevarchi and then turn right onto SC 24 which in 9 km of ascent takes us to Castello di Brolio and to Trivio di La Madonna. We take the first left towards Gaiole in Chianti for about 5 km, then, instead of going right to Gaiole, we turn left to Osteria della Passera and at the next fork we go right towards Lecchi (in the direction of Radda in Chianti). At the next important fork (just before Radda), we go left on Strada Arco del Castello and reach Vagliagli. The long climbs are over, now downhill and rolling sections to Querciagrossa and Lornano, then Castellina Scalo and back to Monteriggioni.