Vintage car tour in the Tuscan countryside

We guess many of you already dreamed of a vintage car tour in Tuscany. It’s really romantic and it’s like being in a movie back in the Sixties. You know, one of those movies where the main character has a polka dot dress and a scarf fluttering in the wind.

We had the opportunity to try a vintage car tour. The starting point was in Badesse, in the countryside around Siena, and the itinerary covers many characteristic little villages in the surroundings that deserve a visit.  Sounds fun and interesting, right? Our lasts about 8 hours and plan your trip along the “Chiantigiana” or SS 222 road, which will take you around the entire Chianti: Badesse: The starting point of our journey with a vintage Fiat 500 was the My Tour offices, the tour operator that organizes the tours. Badesse is a really small village that is part of the municipality of Monteriggioni. Before leaving, since the tour combines vintage Fiat 500 and Vespa Piaggio tours, people are trained about how to manage the new means of transportation. This is very important, especially for those who are used to drive on the left. (In Italy, we drive on the right side of the road and the driver is on the left side.)

Fiat 500 in the Tuscan countryside
Fiat 500 in the Tuscan countryside

Next stop: Fonterutoli. Between Badesse and Fonterutoli you can start to taste the Tuscan countryside, with all those stereotypes that convinced you to plan your holidays in Tuscany! Rolling hills, avenues of cypresses, ploughed wheat fields with bales of hay aside… Everything is dreamy and you could actually be in a dream if it were not for the noise of the Fiat 500 that roars in your ears and that brings you back to reality!

Fiat 500 on a country road
Fiat 500 on a country road

Fonterutoli: Fonterutoli (pronounce Fonterùtoli) is a village in the municipality of Castellina in Chianti, Siena’s countryside. It is located in the heart of the Chianti area and was already known at the time of the Etruscans and Romans. The stop in Fonterutoli is very characteristic not only for the wonderful views but also for its history.

Fonterutoli
Fonterutoli

As you may know, Siena and Florence have always been rival cities. During the wars between Siena and Florence, it was the seat of the agreements that put an end to the dispute of the territories of Chianti. It is said that, according to the agreement, the border should be established at the point of encounter between a knight of Florence and a knight of Siena, which would be leaving from the respective cities at the first crowing of the cock. The meeting between the two knights took place right in Fonterutoli, a few kilometres from Siena but far from Florence, because the knight from Siena remained asleep!

Castellina in Chianti
Castellina in Chianti

Castellina in Chianti is our next stop. Even though this is a small village, be sure to dedicate some time to visiting it because there are several things that worth a visit. The town of Castellina in Chianti is located on a hill at the intersection of three valleys of Arbia, Elsa and Pesa. Of Etruscan origin, Castellina passed under the dominion of Florence from the twelfth century and became an important outpost due to its strategic location along the road that connects Florence to Siena. It was destroyed and rebuilt several times because of the struggle between the two cities, each time with larger fortification walls.

Streets of Castellina in Chianti
Streets of Castellina in Chianti

Today, what only remains of the city walls is the beautiful covered walkway called Via delle Volte, where you can find many shops and restaurants. The path follows the perimeter of the old walls, enclosing part of the historic centre. The main street is via Ferruccio, lined with craft shops, restaurants and buildings that belonged to prominent families in the village. In Castellina you can also find many churches with important pieces of art and the Rocca, nowadays seat of the municipality of Castellina. Inside the Rocca there is also the Archaeological Museum of Chianti, which preserves archaeological finds in neighbouring areas.

Streets of Castellina in Chianti
Streets of Castellina in Chianti

When it’s time for lunch, the only thing that an Italian can think about is a table ful of food! The best idea is to taste something from the Tuscan tradition. What are the foods you can’t miss? Here is a list of top 10 Tuscan must-eat items.

Lunch time under Via delle Volte
Lunch time under Via delle Volte

The last stop is in Monteriggioni, an iconic and perfectly preserved walled town. Guess why they need to build a solid wall and 14 very high towers? Right! For the never-ending rivalry between Siena and Florence! Monteriggioni is small but very characteristic and it makes precisely the idea of a medieval Tuscan town. You can enter both from Porta Franca or Porta San Giovanni and already be in the heart of the village. The main square is called Piazza Roma, which features the Romanesque and Gothic Church of Santa Maria Assunta. You can read more about Monteriggioni in this post.

Monteriggioni - Piazza Roma
Monteriggioni - Piazza Roma

Would you like to try a vintage Fiat 500 tour? You can find it at My Tours, a tour operator that organizes many experiences in Italy such as Vespa tours, bike tours, cooking lessons, etc.

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