The first stage is quite easy, if not for the three kilometers of climb that you have to face, after passing the Tignano castle, in the Valle degli Alpaia. Poggibonsi is soon visible from the end of the valley and after reaching the Point, but you will have to be equipped to cross it all.

Right after leaving Poggibonsi, making a detour to visit the old part might be worth it, with the fort of Poggio Imperiale, the Archeodrome and Fonte delle Fate. To leave the city, you take the SP130 road of Castagnoli, and follow it up to the Spedaletto crossroad. Now, the white road starts going up towards Bibbiano and Lilliano and the vineyards dominate this typical Chianti landscape. After the Vallechiara lake but in Cornia, at the view of another lake, a slope allows you to take a deep breath, mixing with the wonder felt at the sight of Molino di Bombi, a magical place where you could spend the rest of eternity if you would not have to delve in a deep forest and try entering the SR222 road, right after passing through Fonterutoli. The castle of Fonterutoli is an ancient Florentine fortress in defense of the Sienese excursions, and a medieval border area between the two, established with the famous challenge between two knights from the two cities, one to a black rooster's crow and the other to a white rooster's crow. Castellina in Chianti waits for the cyclist at this Point, with the knowledge that his stop will not be short given the accumulated fatigue and the many temptations this town offers.

From Castellina in Chianti you go up along the SP76 road that climbs among many hills: Poggio Fulvo, Poggio Auzzo, Poggio di Ricavo and Poggio Macia Morta, certainly the most well-known among cyclists. Right in Macia Morta, you reach an altitude of 625 meters, the highest point of the trip. The hills on one side and the beautiful view on the slope on the other, look over the valley, rich in vineyards placed among the woods. Finally you descend and see the Madonna di Pietracupa, anticipating your arrival at the village of San Donato in Poggio, a beautiful medieval village with well preserved walls and many things to see, such as Palazzo Malaspina and the Roman parish church. San Donato maintains the tradition of “pranzo dei bifolchi” alive, held in the oratory of the Sanctuary of Santa Maria delle Grazie in Pietracupa. The lunch, prepared by men alone from the first light of dawn, has the stracotto as its protagonist, cooked very slowly in large copper pans. You make your way back to Tavarnelle in an ecumenical way, meeting the church of Santa Maria del Carmine in the town of Morocco and the Roman parish church of San Pietro in Bossolo. But if the religious buildings encountered on the way were not enough for you, you can always try searching for the church of Santa Lucia al Borgetto in Tavarnelle or reach the church of San Bartolomeo in Barberino, with a beautiful view on the Chianti hills.