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Wonderingaround Chianti


  • Monuments
  • 8 Hours
  • *Guide
  • Views
  • Tablets
  • *Tasting


Chianti is a hilly territory that stretches between Siena and Florence, but also slightly across Arezzo. The landscape is mainly covered by woods, vineyards, remote parish churches, castles and typical Medieval villages.


The Etruscan people, (probably coming from Asia Minor), had a crucial role in the future and panorama of Chianti. Among the most characteristic villages of this area we can find Castellina in Chianti whose rich history is attributable to the Bronze Age and the Etruscans. Around halfway through the thirteenth century, it becomes a member of the Chianti League, together with Radda and Gaiole. At the beginning of the fifteenth century, Florentines decide to reinforce their location, by building a ring of walls and a fortress. Even the famous architect Filippo Brunelleschi is consulted during the ongoing reconstruction. Another centre of great importance is Panzano, located halfway between Siena and Florence, of Roman origines, while first settlements date back to the Etruscan age. Because of its position, as well as lots of other nearby centers, it has frequently been involved in many feuds between the two cities. Last but not least, there is Gaiole in Chianti, a small market village ( meant to serve the various nearby castles), which in the XIV century becomes the “terziere” chief town (meaning that it represents the main town of the three districts, part of the same area) inside the Chianti League. Being yet a well-known trading centre, the district is plagued by forays and constant raids, up until 1555. That year Siena ultimately surrenders and is annexed by the “Granducato di Toscana”.


Get on board of one of our vintage Fiat 500s and we will drive you through an interactive tour experience. To reach Gaiole in Chianti, a small but lovely village, after setting off from Siena, you will traverse a countryside road, immersed in the greenery of the woods, from where you will be able to enjoy the striking views that overlook the countryside of Chianti, renowned for its wines. It only takes a few minutes: you can park your Fiat 500 and visit Castellina in Chianti, at your own leisure, while sipping a tasty glass of red wine. Thanks to our supplied tablets and informative videos, you will be free to enjoy the timeless beauty of the place. Before heading back to Siena again, you will cross the gorgeous centre of Panzano in Chianti and Monteriggioni, which is one of the most stunning fortified villages of Italy, famous for its towers.

*on request


  • Rental of a vintage Fiat 500
  • Interactive journey with the GPS
  • Informative leaflet
  • Tablet
  • Interactive videos with explanations about history and art
  • Welcome Kit
  • Car insurance, driver, passenger, taxes, petrol


  • Each vintage Fiat 500 can carry max 3 passengers
  • Each driver must own a valid driving license (Italian or foreign one)


--- PROMOTION 2024 ---

Rental of a vintage Fiat 500 (1-3 people) all inclusive 190 € (excluding VAT)


  • One person — driver 140 €
  • 2 people — driver + passenger  120 € (tot. 240 €)
  • 3 people — driver + passengers 100 € (tot. 300 €)

Con il contributo di Fondazione Montepaschi Bando IKIGAI (2019)