I had seen the impressive walled town of Monteriggioni sitting on top of a hill many times while driving on the highway between Florence and Siena. Then one day I finally had the time and made the turn off to see what is hiding behind the medieval walls. I have found a cute village, definitely worth a visit.
Just like other fortified villages in Italy, Monteriggioni's history started as a castle at the beginning of the 1200s. It's about 20 kms away from Siena, in the direction of Florence, so it had a strategic position defending the territory of Siena in the constant fights between the two rival cities. Finally the castle was conquered by Florence in the 16th century and Siena with its entire territory was taken over by the Medicis.
The 570-meter wall remained beautifully intact, 11 of its 14 towers you can see even today. It was built with two gates, one facing Rome, the other one facing Florence. You can even walk on the wall for a small fee, it's definitely worth the experience and you can enjoy the stunning view of the Tuscan countryside. With its tall and thick walls the castle was standing strong, even the Florentines had a hard time to occupy it.
The historical center completely kept its medieval character, with its stone houses and narrow cobblestone alleys. You will also find a couple of cafés and wine shops here, so you can pick up a bottle of Chianti Classico.
For families with boys the Armoury Museum can be a fun activity. I did not go inside, as I am not much into armours and weapons, I rather just spent some time sitting on the Piazza di Roma with a caffè latte, doing some people watching. You can also visit the 13th-century Church of Santa Maria Assunta on the square.
The castle was so famous even Dante wrote about it in The Divine Comedy.
Unfortunately I never had the chance to visit it, but the Monteriggioni medieval festival is said to be fun. It's actually one of the most popular festivals in Tuscany. It takes place in July, please check the exact date if you are travelling in the area during the summer and let me know how you liked it.