This first easy stage allows you to learn how close the two centers of this municipality really are. After Tavarnelle, at the same height of the ancient Franciscan convent of Santa Lucia al Borghetto, you quickly reach Barberino from Porta Fiorentina, near the old Ospedale dei Pellegrini hospital, and leave it from Porta Senese. From here to Poggibonsi, you descend following the SR2 Cassia road, surely the most popular for motor vehicles and the one where you should be the most careful. The Point is situated near the city’s Stadium.

Here, you leave Poggibonsi from Via del Chianti street and take the SR429 road that, for 18 km, climbs up towards Castellina in Chianti. Known as the Pestello slope, it never reaches an elevation higher than 6% and it therefore is all to be enjoyed, both for its view and for its meetings, such as the Canonica di San Pietro a Cedda and the parish church of Sant’Agnese in Chianti, situated right at the entrance for the Sant’Agnese Natural Reserve. The forest is the keeper of the historical cypress wood, a true monument and shelter for various species of birds. You can rest and replenish in Castellina in Chianti since the opportunities this historical and well-kept center offers are many.

Short and mostly easy stage, although not free of slopes. After reaching 616 meters of altitude in a stunning landscape of forests, vineyards and olive trees, you can climb down towards Radda, the ancient headquarters of Lega del Chianti. You enter the historic centre from Porta Fiorentina and leave it from Porta Valdarnese, after admiring the Podestà Palace and the Church of San Niccolò, to have a well-deserved rest at the Point situated under the trees of the public gardens.

This stage flows easily in a nice descent until meeting Lucarelli, situated along the “Valley of Gold”, named after the many diggers looking for gold nuggets in the Pesa river. True or false, go ask the typical well-known shop located along the street how many sandwiches were sold in that period. In order to head back to Tavarnelle you have to leave the SR222 for a beautiful secondary road heading towards the towns of La Piazza and Sicelle, ancient municipalities that still maintain their churches and, along the road bringing to San Donato in Poggio, a fortified building called, after its owner, the Michelangelo Tower in plain sight. But the surprises are not over since, after entering the SP101 road, you will find yourself in front of the Madonna di Pietracupa, anticipating the medieval town of San Donato in Poggio with its suggestive little watchtower and its two doors, the Fiorentina and the Senese. Before reaching the Point in Tavarnelle, Morrocco, a stop at the Monastery of Carmelitane Scalze is definitely worth it and, if tired of cycling and wishing to see Chianti from above, turn your gaze to your right to find, with a little luck, who will propose you to go for a ride in a hot air balloon.