Only 50 kilometers from Florence, and 15 from Siena, lies a tiny, walled 13th century Medieval town that seems to have been preserved in time, its prowess is even quoted in Dante’s Divine Comedy. Used as a defensive fortification in the Middle Ages between the always-fighting Siena and Florence, it is one of the best preserved towns from this era in all of Italy, with 570 meters of circular walls that beckon to the time when everyone wanted a piece of the action.
The view of the Sienese countryside is breathtaking and inside the walls you can visit the Pieve di Santa Maria Assunta, shop for artisan pottery or visit the local museum displaying reproductions of ancient armour. For more ideas, check this site.
Truth be told, even just walking through the charming, tiny streets is a real treat, the town is quite small and completely walkable, we recommend avoiding crowds by visiting in off-season (October-Feb) or in early evening when the summer light starts to fade away. Away from the crowds, you can only imagine the scenes that took place in front of the Porta Franca or Porta di Ponente (facing Florence) hundreds of years ago. Bring a light jacket, even in summer, as the nights tend to be quite cooler.
Best reachable by car, there is a parking lot at the bottom of a hill where you can then walk up to stroll the charming, cobble-stoned streets. Its strategic location makes it an ideal half-day trip from Siena, Florence or Volterra, we recommend stopping for lunch first at Bar dell’Orso by the Monteriggioni exit, well known among locals as the spot for wonderful cured salami, cheese and various Tuscan favorites.