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Monteriggioni and the Montagnola Senese


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


Monteriggioni represents one of the most beautiful fortified villages of Italy. Halfway between Siena and Florence, the village was built by the Sienese between 1213 and 1219 with only defensive purposes; its strategic position allowed the town to control Colle Val d’Elsa and Staggia. The ring of walls is composed by 14 majestic towers and 2 doors:on one side the Porta Franca or “Romea” facing towards Rome, on the other one, the Porta Fiorentina, looking towards Florence. The village dominates the entire surrounding areaand it has been kept incredibly preserved. The Montagnola senese, famous for its coppice woods and karstic caves, represents an area filled with castles and ancient parish churches, among which stand out the complex of Abbadia a Isola, Pieve of Ponte allo Spino and the castle of Montarrenti.


22 August 1553: Monteriggioni is attacked. The city walls of the small village have been craved for a long time by Siena and Florence, the two cities that will lead the battles and will always be against each other. Sienese were inside, Florentines outside the walls. Then the decline begins. No longer does the castle have its defensive role when the entire Sienese state is annexed to the Florentine one: for this it is to blame a traitor, who would have then been tormented by regret.


Get on board of one of our vintage Fiat 500s and we will drive you through an interactive tour experience. To reach Monteriggioni, after leaving Siena, you will travel along a country road, from which you can enjoy suggestive views overlooking the Chianti countryside, famous for its wines. It only takes a few minutes: you can park your Fiat 500 in the square indicated by the navigator and visit the famous castle in complete autonomy. Upon returning, you will travel along the fascinating roads in the woods of the Sienese hill, passing through enchanting villages such as Abbadia Isola, an intermediate stop on the route. Interactive videos will guide you to discover the fascinating abbey founded in 1001 by Countess Ava, daughter of Count Zanobi and widow of Ildebrando Signore di Staggia and Val di Strove. Before reaching Siena again, you will cross the famous Ponte della Pia, of Romanesque origin, which connects to the legendary figure of Pia dei Tolomei, and the Pieve di Ponte allo Spino.

*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 130 € (excluding VAT)


  • One person — driver 100 €
  • 2 people — driver + passenger  80 € (tot. 160 €)
  • 3 people — driver + passengers 70 € (tot. 210 €)

Con il contributo di Fondazione Montepaschi Bando IKIGAI (2019)

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