Despite being a short route, the trail is nonetheless quite difficult due to a long climb that can test even the most trained riders.
Starting in piazza Gramsci, where you’ll turn to the left and climb up in the direction of Montaione’s historic centre. At the stop, turn left to merge with viale da Filicaja and head down the slight descent. After about 700 metres, at the end of the descent, pass by the fork for San Vivaldo on the right, instead taking the left for via delle Colline. After about a 1-kilometre descent, you’ll come to another fork in the road; take the left. After about 200 metres, turn right onto a dirt track flanked by rows of cypress trees.
After an initial flat stretch of road, roughly 600 metres, a descent begins that offers views of Gambassi Terme.
You’ll soon come to an abandoned building; continue down the road, flanked on the left by a vineyard, before coming to the valley. Here, you’ll find another fork in the road, where you’ll need to turn right. After about 100 metres, cross a small bridge over the Rio Pietroso stream. This is where the climb upward begins, which stretches on for about 2.7 km. The first part is a fairly steep climb on a pebbly road. After about 500 metres, you’ll come to a vineyard. Further on, you’ll come to a small farm building and be able to enjoy a view of Gambassi Terme.
After about 100 metres, close to the parking lot for an agriturismo, the road flattens out. Keep to the left, where the road is flanked by vineyards and olive groves. Near a fork, the road begins to climb upward again. As you slowly head up the road, bordered on the right by a fence, you can admire the stunning landscape of the hilly Valdelsa. After a kilometre, you’ll come to via Volterrana, a paved road on right.
After about 700 metres, you’ll find the Church of Santa Cristina, while on the right, you can still admire the Valdelsa landscape. Another 500 metres on, leave via Volterrana and merge onto via Poggio all’Aglione on your right. The road will begin to climb upward for about 250 metres before descending again.
After a few curves, the road straightens out, allowing you to enjoy a breath-taking view that stretches all the way to the mountains overlooking Florence. Pass by the Roman Cistern before arriving at a fork in the road with via delle Colline. Turn left onto via Leonardo da Vinci and continue until you’re back in Montaione.