Setting out from the Castle of Monteriggioni, the route goes over some parts of the Via Francigena, the ancient system of roads that crossed the Montagnola, arriving at Abbadia a Isola, with its wonderful Romanesque Church of SS. Salvatore e Cirino, before then continuing towards Certino di Sopra, along a paved way going slightly uphill. Arriving at Casa Giubileo, where there is a stopping-off place, ancient history mingles with an episode in more recent history, and a sadder one, involving WW2 partisans: from here, continuing along the CAI 100 Route, down an unsurfaced path allowing cyclists to travel at high speeds, you return to Abbadia a Isola, and continue on to Valmaggiore, a pleasant plain that marks the spot where there was once a swamp: “Padule del Canneto”. Arriving at a crossroads with a tree in the middle, make sure you take the left-hand turning, as signposted, leading to the ancient osteria of Il Mandorlo (originally 16th century). You continue in the direction of Casella, Fioreta and Sparviero, until you get to the SS del Pian del Lago (state road); the subsequent sections, after Fungaia, are a succession of challenging single-track paths.
This is one of the most attractive and highest parts of the route, with panoramic views over the Sienese countryside, with areas of dense undergrowth full of local wildlife. The descent towards Castel Pietraio is fairly difficult, and you have to pay a lot of attention to the trajectory, especially if the ground is damp underfoot. Returning to Abbadia a Isola, and continuing once again  towards Valmaggiore, at the crossroads with tree turn right towards Podere Ebbio, and from here on the same route as before: Il Mandorlo, Casella, SS.2 Cassia.
The last section of the route crosses Podere Il Santo and continues along the challenging arrival of the Gran Fondo, along the unsurfaced climb with a maximum incline of approx. 25%, leading, via Porta Fiorentina, directly to the inside of the castle.

CAI Routes: 101-100-102-106

Route courtesy of Team Bike Pionieri

Download the brochure "Pedalare sulla Francigena" (726.9 KB)

Along the itinerary

Fungaia Casa Giubileo La porcareccia Castelpietraio Abbadia Isola La posta The medieval borgo of Monteriggioni