The fortified village of Monteriggioni was founded in 1214 and formed the northern bastion of the Republic of Siena’s territory, often finding itself on the front line in the power struggle between Siena and its arch rival, Florence. Originally, the outpost served as a garrison for Siena’s soldiers and the main Piazza Roma was the vegetable garden that kept them fed in times of siege; today there is a scattering of bars, restaurants, and souvenir shops to keep modern invaders happy. The town’s 13th-century walls incorporate 14 well-preserved towers, so iconic that they were mentioned by Tuscan poet Dante Alighieri inThe Divine Comedy.
Monteriggioni is a popular stop on day trips to the Chianti region of Tuscany from Florence, Siena, and Pisa that explore the countryside surrounding San Gimignano, Montecatini, and Volterra; full-day sightseeing tours generally include lunch and a wine tasting of local Brunello di Montalcino wine. You can also explore the area on foot by joining a Tuscany hiking tour, or zip down the country lanes on a scooter during a Vespa tour.