Leave from Piazza Gramsci in Montaione and turn immediately left onto Viale Filicaja you will start to go down to the crossroads with the road towards San Vivaldo. Then turn right and follow the road that in the first stretch is slightly downhill and then begins to go up during the last few kilometers to San Vivaldo.
Once in San Vivaldo, near the Chapel of the Ascension that you can see on your left, and that is part of the Sacred Mount of San Vivaldo, take the road to the right in the direction of Iano. Go down at full speed for a few miles on a road that sometimes is covered by trees, until you get to the village of Iano (town once famous for the extraction of Onyx) where you can refresh yourself with a cool drink in the cafeteria of the village or a little further in the restaurant for a quick bite before heading in the direction of Villamagna. During this descent is worth to slow down and enjoy the fantastic panorama that opens onto the Tuscan countryside: to your right you will see the village of Castelfalfi that dominates over the golf course, while in front of you in the distance and perched on a high hill you can admire Volterra.
Continue for another 7 km pedaling effortlessly on the ridge of the hills until you meet a short ascent of about 1 km that will take you straight to Villamagna. It ‘s nice to see how the landscape changes becoming wilder and more barren with hills as far as the eye can see, typical of the Volterra countryside.
Cross the small village of Villamagna: a few houses, a couple of Tuscan shops and if the weather is nice, you will be able to see some Tuscan elderly sitting and watching you while you fly at full speed in front of the village with the bike: you will be the news of the day!
After the town of Villamagna the road continues downhill for 500 meters until you come to a junction: take the road on the right towards Peccioli and continue down through an avenue of cypress trees for about 2 km until the next junction where you turn right following the signs for Peccioli. The road continues for another 2 km on a false plain among the barren hills of the Val d ‘Era to the junction for Montelopio.
Turn left to Montelopio: here begins a winding ascent sometimes tough made of hairpin bend going through a long avenue of cypress trees that will be with you for 3 km until the characteristic town of Montelopio.
Once in Montelopio you will be welcome by a wooden crucifix. Continue on the left descending from the town of Montelopio for 1 km and then go on the plain.
After about 2 km you will reach Fabbrica where a crucifix will welcome you to this charming little village. Pass this characteristic village without losing the typical Tuscan small shops such as the butcher, the baker and the grocer then head to Peccioli.
Here the road continues for about 6 km on a false plain interrupted by a slight up and down through a country where the undisputed protagonist is the Tuscan olive tree.
A high bell tower will welcome you in Peccioli where we suggest to make a brief stop in the historic center to catch your breath and visit the ancient church and alleys of this ancient Tuscan village. From Peccioli follow the signs for Pontedera and after a 2 km descent you will reach an old tobacco house where you have to turn right towards Castelfalfi.
After about 2.8 km turn right following the signs for Legoli – a quaint little village situated on top of a hill – which worth a visit. Here we began to climb for about 2.7 km until you get to Legoli. After passing through the town, the road is downhill for another 2.8 km to the junction on the road. At the junction, continue towards Castelfalfi that from here is about 3.6 km away.
Once in Castelfalfi it is worth making a brief visit to the castle and the Church of SanFloriano in addition to enjoying a breathtaking view: it is the right reward for the efforts of the pedal.
Leave to San Vivaldo, that you will reach after 4 km on a road slightly uphill, and at the junction turn left towards Montaione travelling again the initial stretch of the trail for about 10 km.