Starting from the Airbnb in Montespertoli, the tour goes south. You drive through Poggobonsi, which is quite busy.
Monteriggioni is a beautiful medieval town situated on a hill from which you get a beautiful view of the surrounding vineyards and olive trees. The unique decor of this medieval fortress has also not escaped notice by some well-known film directors who used it in their films. The most famous are The Gladiator by Ridley Scott, The English patient by Anthony Minghella and Tea with Mussolini by Franco Zeffirelli.
Monteriggioni was built between 1214 and 1219 on the Monte Ala hill. The town is still completely surrounded by its medieval city wall of no less than 570 meters long, along which 14 watchtowers have been installed. Initially there was a moat on the outside of the city wall that was filled with wood and other combustible materials to deter attackers from attacking the city. However, this moat was filled in the 15th century. The beautifully preserved city walls can best be seen from the road that leads over the hills of the Val d'Elsa. Monteriggioni is only accessible from two city gates: the first facing Siena and the other facing Florence. The small center of Monteriggioni consists of medieval houses and a large central square, the Piazza Roma, on which the church Pieve di Santa Maria Assunta gives out.

You drive further south along beautiful quiet lanes.
The Abbazia di San Galgano shines in the middle of the Tuscan countryside, some forty kilometers southwest of Siena. Despite the fact that this abbey no longer has a roof and no beautiful frescoes or stained glass windows to admire, it is one of the most beautiful abbeys we have ever seen in Italy. The abbey was built in the thirteenth century and was in use for a long time. The monks lived here in silence, in harmony with nature and the seasons. Unlike in other churches, the beauty here does not lie in frescoes, domes and altarpieces, but in the interplay of stones, light, shadow, sun and clouds. Every corner is different, new surprises await at every moment of the day in combination with the ever-changing sky.
From here you can easily walk to the hermitage of Montesiepi, which is located on a hill. Here too there is a mysterious atmosphere, largely due to the special relic that is kept in the chapel: the sword of San Galgano. The floor of the circular chapel is interrupted by a piece of rock, from which a small piece of a sword protrudes. The sword is said to have ended up in the stone in 1170, according to a well-known legend at the hands of Galgano, a knight.

Colle di Val d'Elsa is a beautifully built town. The upper part of Colle Val d'Elsa is also called Colle Alta, and the lower, more modern part Colle Bassa. The Colle Alta is the relatively unspoilt, medieval part of the town that contains many intriguing sights. Visit the impressive cathedral where a religious artifact can be found; namely a nail of the Cross! Thirty of these nails were brought to Tuscany from the Holy Land and this one is considered one of the few still in existence. Every September, the 'Festa del Santo Chiodo' is held to honor this relic. The town is blessed and a procession is held of which the relic is the centerpiece. The archaeological museum is located near the Piazza del Duomo. This is considered one of the best Etruscan museums in Italy and is an enriching experience for anyone wanting to learn more about the history of this region. The more modern part of the city, Colle Bassa, lies further down and is best known for the crystal industry. The local crystal museum explains that Colle Val d'Elsa produces more than 15% of the world's Crystal!
You approach the end of the ride via Certaldo.