You leave in Montespertoli where you can rent a holiday home (airbnb). You drive south to the Chianti region.
The Abbey of San Michele Arcangelo a Passignano (Italian: Abbazia di San Michele Arcangelo a Passignano) is a Benedictine monastery in the municipality of Barberino Tavarnelle between Tavarnelle and Greve in Chianti. It is located on top of a hill from which you get a beautiful view of the lower vineyards. The church, built according to a Romanesque floor plan from the 12th and 13th centuries, still retains its original function as an abbey church. The facade also dates from that time. The church was renovated several times in the following centuries and it was richly decorated in Baroque style. The inside is impressive with its beautiful frescoes.

Castellina in Chianti is located on a hill in the middle of the valleys of the rivers Arbia, Elsa and Pesa and in the 13th century was the capital of the Lega del Chianti, which included Gaiole in Chianti and Radda in Chianti. The medieval character of the town can still be found in the narrow streets, the castle and the remains of the city walls. The medieval castle of La Rocca is located on the highest point of Castellina, it dates back to the 11th century and is still in very good condition. The archaeological museum has been housed in it since 2006

Greve in Chianti is famous for its market square, which has been visited by residents of castles and walled towns since the Middle Ages. This square has a triangular shape and large porches, so that everyone was protected from the weather. In the center is the bronze statue of Giovanni da Verrazzano; discoverer of New York harbor. In front is the church of S. Croce; Renaissance style, renovated medieval church. The church contains works of art, such as a triptych depicting Madonna and the saint of Bicci Di Lorenzo.
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.

When approaching Firenze it gets a lot busier on the track. Just north of Firenze is Fiesole. The place is located on a mountain slope, overlooking the valley of the Arno and the nearby city of Florence.
Fiesole was an important city of the Etruscans. After this people came the Romans.
It is best to park in the immediate vicinity of the central square. You can't miss Il Cattedrale di San Romolo, or Il Duomo di Fiesole. From far and wide you can see the tower proudly protruding above everything. The cathedral was built in 1028; the bell tower was only built in 1213. The Romanesque style can be found both on the outside and the inside. The sober decor is brightened up with a number of beautiful works of art, such as the series of frescoes above the choir. When you buy Via Giovanni Dupré you will see right in front of you the entrance to the Teatro Romano, the theater built by the Romans. You will also find remains of the Roman bathhouse here. In the accompanying museum you can see a number of Etruscan finds in addition to Roman pieces.
You drive a little further north and then turn back through the outside of Firenze to the holiday home.

This route receives 4.5 stars. The roads are excellent. The beautiful nature through the vineyards of the Chianti region offer very beautiful views. Culture and nature are amply covered on this ride.