Medieval tour: Siena, San Gimignano and Monteriggioni

The region of Tuscany displays evidence of various epochs, starting with the Etruscan age. The Middle Ages, an era from the 5th -15th centuries BC, left a clear mark on many cities starting with Siena, one of the most popular tourist destinations in Italy.


The Palio in Siena is a world-famous event and attests to the strong ties between the city and its past. This is not a reenactment: rather, the Palio is a ritual which has been repeated year after year for centuries, and to think, the oldest document regarding the race dates back to 1238. In 1995, Siena was proclaimed a UNESCO World Heritage site thanks to historical edifices like the ancient City Hall in Piazza del Campo, the most visited tourist location. The Duomo with its colourful marble is a masterwork of Italian art, and there are no words to describe a similar spectacle. You must see it with your own eyes. 

San Gimignano

Don't be fooled by this city’s small scope: San Gimignano contains numerous Medieval buildings in its impeccably preserved historic centre. Despite the renovations carried out between the 18th and 19th centuries, the Medieval atmosphere of the city is still intact, representing a clear example of town planning at the time. Did you know that San Gimignano is nicknamed the “Manhattan of the Middle Ages”? This is because of the numerous towers that once characterised the city with an effect similar to that of a modern metropolis. You can still see many: 14 to be exact.


The Porta Franca (or Romea) is not only the entrance to an enchanting village, but also a sort of time machine which brings visitors back to the Medieval era. The Montereggioni Castle was constructed by the Republic of Siena between 1214 and 1219 with the objective to create protection against the forces of Florence. The outpost has survived until the modern day, resisting attack after attack. Monteriggioni inspired Dante Alighieri, who makes mention of it in some verses of his Divine Comedy, but has also had prominence in the world of video games. In fact, the little village in the province of Siena was used as the setting for the Assassin's Creed game.

Why choose the “Medieval Tour: Siena, San Gimignano and Monteriggioni”?

To discover the most authentic Tuscany means that you must also get lost in time. Our knowledgeable driver will pick you up at your hotel, and if you want, local guides are available to you. 

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