You set off from Parco Il Poggione to walk along the medieval walls and, from Via Borromeo, leave the town, not without having met two of the many noble villas scattered in the territory: Villa Il Fedino and Villa Borromeo. You climb up and down between the villages of San Pancrazio, with its beautiful Roman parish church, and Fornacette. The slope leading to the towns of Lucardo and San Donato, both equipped with beautiful churches, is certainly demanding. The villages of Fiano and Marcialla anticipate the entry for Tavarnelle Val di Pesa from the SP49 road from which, with a short deviation, you can reach the Church of Santa Lucia al Borghetto, an ancient Franciscan monastery. The Point is located in Piazza Matteotti, in the city center.

Another stage of medium difficulty. From Tavarnelle you take a suggestive secondary road that, between vineyards and forests, leads to the town of Tignano with its castle. After reaching the SP101 at a crossroad not far from San Donato, you climb up following the stunning and panoramic road leading to the Point in Castellina in Chianti, situated right in close proximity of Via delle Volte, roofed walkway built by Filippo Brunelleschi.

Route starting from Castellina in Chianti, following the SR222 road until Santa Maria in Grignano, a little further from the Pesa river. Following the SR222 road up to Panzano means crossing a sea of vineyards and admiring the dream views. Panzano is not lacking the "ciccia" as the poet-butcher Dario Cecchini likes to call the fine meat. You make your choice for a day or even night stay, but surely there will be no way you will regret it: the road leading to Greve, the most famous market of Chianti and where, like the residents like to say, you’re soaked in wine.

From Greve you take off from the statue of Giovanni da Verrazzano, placed right in the middle of the characteristic triangle-shaped square. The crossroads to go have a pleasant visit to the castle that gave birth to the famous navigator of '500, is not far away from Greve, situated between the two towns meeting on along the SR222 road, Greti and Le Bolle. Cycling through the hills with views on vineyards you will meet other villages like Chiocchio, Strada in Chianti and Santa Cristina. The scent of the city of Lilies is increasingly intense and becoming almost enveloping as soon as you leave the town of Greve and, for a bit, from Chianti; Impruneta and Tavarnuzze clearly mark the vicinity to Florence, the purple city. Chiesanova, the town of Schiacciata, is known for its beautiful little lake. Now that we are back home, in San Casciano and in the following towns, from Romola to Cerbaia, smell once again like Black Rooster. At Cerbaia it is advisable to take a good breath because the next 4 kilometers leading to the gates of San Casciano have slopes in double digits. A stop in the Roman parish church of San Giovanni in Sugana can help, but a slow pace with your head held high is still needed. After arriving in San Casciano the only thing left to do is to enjoy a well-deserved rest, constantly supervised by the Cervo by Mario Merz, a modern sculpture placed on the medieval city walls.