A walled city sitting on top a strategic hill overlooking the Tuscan countryside, the town of Monteriggioni is a charming stop on the way to Siena and San Gimignano.
Built between 1215-1219 by the Sienese as a fortification against Florentine forces, this gorgeous example of Medieval architecture takes about an hour to explore and is one of the best places in Tuscany to take enviable photos.
The town was attacked numerous times by Florence during its existence, until the last commander of the city (Giovannino Zeti, an exiled Florentine) simply handed the keys to the city over to Florence in an act of reconciliation and was thus absorbed into the Republic. A "great betrayal" for the town's inhabitants.
Unlike its violent past, today visitors can stroll a beautiful piazza in the town lined with the houses of the town's elite families, along with a small Romanesque church. A few cafés and restaurants are also sprinkled throughout the town's picturesque streets, as are shops selling local gastronomy and artisanal goods. Yes, most - if not all - of the outposts are super touristy, but it's Italy so the quality is definitely better than you would find outside the country.
The walls of the city are almost 1,900 feet in circumference and are climbable, as are many of its original 19 towers and two gates that served as the only entry points to the city.
Monteriggioni a bit difficult to get to if you're visiting Tuscany without a car, however many tour operators from Florence and Siena offer pit stops to the town, oftentimes combined with tours to San Gimignano.