The GATE location in Monti already leads to a doubt: Monti di Sopra or Monti di Sotto? Either way, the first stop, after a descent and a brief plain area, avoiding the Passera tavern, offers an uphill with a landscape adorned with stunning vineyards up to San Sano, the beautiful town of the «Beona Frog», and then follows a country road towards Lecchi, famous village also known as "the cyclist’s den". From Lecchi you climb up a few reasonable slopes, then descend between woods and climb up again, meeting the detours heading to Ama and Montebuoni, only to descend and climb up one last time towards Radda’s GATE, the ancient capital of Lega del Chianti situated in the heart of Chiantishire. Radda, village of “stone and wine”, is a typical Sienese town where the territory anticipates the Florentine one. It deserves a visit and a stay, even if just for enjoying some local deliciousness.

From Radda, a beautiful regional road with little to no traffic heads towards Castellina in Chianti, moving along the Petroso Hill and reaching a total of 615 meters of maximum height. The trip is extremely pleasant and never hard with beautiful panoramic sights.

This is the longest and most demanding stage. Descending towards Pietrafitta is a joy that anticipates the turn, after a short climb, heading to Lucarelli, a small town famous for the large number of adventurers visiting it, searching for gold by the Pesa river. For this very reason, the cyclists pursuing this long but easy slope heading to Radda in Chianti love telling stories about cycling through the gold valley without success. Leaving the desires of wealth behind, you return to the vineyards of Vistarenni and briefly pass Gaiole in Chianti, where the Bottega di Gaiole, a sort of vintage museum of great taste, definitely deserves to be visited. After surpassing the crossroad for Monteluco and Castagnoli that you reach after a discreet climb, the Meleto castle is of great interest, with its precious and tiny little theater, certainly one of a kind. From Castagnoli, you climb down to meet the crossroad for the Brolio castle from which, after surpassing Cacchiano, you reach Monti again. The choice is still the one between Monti di Sopra and Monti di Sotto, but our advice is to take away all the bad thoughts from your head and get purified in the parch church of San Marcellino.