The route departs from the holiday home in Montespertoli. You drive south to the Chianti region: green hills, interspersed with impressive vineyards, olive groves and romantic small towns. It couldn't be more typical Tuscany. The height differences are not great, but there are still a lot of climbs. The courses wind their way through the beautiful landscape. Via the winding track of the SR429 we arrive in Castellina in Chianti.

Castellina in Chianti is located at an altitude of almost 600 meters in the middle of the valleys of the rivers Arbia, Elsa and Pesa and, together with Radda in Chianti, is undoubtedly the most beautiful of the 4 Chianti towns that lie on the territory of Siena. In the 13th century it was the capital of the Lega del Chianti, which also included Gaiole in Chianti and Radda in Chianti (which we drive a few km further). The history of Castellina in Chianti goes back to the Etruscan period, but more significant are the traces of the Middle Ages that can still be found in the narrow covered streets (via delle volte), the castle (la rocca) and remains of the city walls.
Via delle Volte: This narrow medieval street is the longest vaulted street in Tuscany. It starts and ends in the main street that crosses the historic center. In the street there are several shops and a restaurant where you can find refreshment on the terrace in the hottest part of the day in the summer.
Tumulus de Montecalvario is an Etruscan burial mound located near Castellina in Chianti. This name was given to him because of its location at the last station of a Way of the Cross. It has a circular diameter of about 53 meters, consisting of four tombs, with main room and lateral cells, with the entrance facing the four cardinal directions.

Radda in Chianti is undoubtedly the most beautiful of all and therefore also the most visited. The town still retains its original medieval elliptical ground plan, remains of the city walls and covered medieval alleys, unique in their genre. It is therefore pleasant to walk in the streets between the many monuments, squares, shops, restaurants, typical shops, etc.

You make a short detour to Volpaia. This village is somewhat hidden. The road that leads to the village is worthwhile in itself and winds its way through vineyards and olive groves. Then, after the umpteenth corner, there is suddenly Volpaia. Or rather, the Castello di Volpaia. Like almost everything in the Chianti region, Volpaia has a long history behind it. It is said that the construction of a fortress or castle on this site started as early as the 10th century AD. In the centuries that followed, the importance of Volpaia - strategically located virtually on the border between the rival city-states of Florence and Siena - grew steadily. And so the defenses were also expanded. When the hostilities between Florence and Siena finally ceased, the defensive function of Volpaia became less important and developed further with churches and buildings for habitation. This is how Volpaia was created, which can now be visited: a lovely, small town in a picturesque setting.

You continue to Panzano in Chianti. This is located at an altitude of 507 meters, which gives you a beautiful view of the surroundings and the underlying Chianti DOC vineyards. It has a small historic center and cozy restaurants.

The route ends at the holiday home via Greve in Chianto and San Casciano in Val di Pesa.

This route receives 5 stars. The route passes through green hills, interspersed with impressive vineyards, olive groves and romantic small towns. The height differences are not great, but there are still a lot of climbs. The courses wind their way through the beautiful landscape.