Monteriggioni

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.

• The rolling hills of Chianti comprise one of the most picturesque corners of Italy, so be sure to bring your camera.

• The town is accessible to wheelchair users, but if your visit is part of a wine tour, wineries may not be. Check in advance.

• Tours of Monteriggioni and the villages of Tuscany require a fair bit of walking. Choose comfortable shoes and dress for the weather.

By car, take the Firenze-Siena highway and exit at Monteriggioni. Arriving by public transportation involves multiple bus connections, so the most convenient way to visit is by joining a small-group or private tour that includes transportation.

Monteriggioni hosts a Festa Medievale (medieval festival) in late July, one of the most famous medieval pageants in Italy, with music and dancing, feasting and merrymaking. The Chianti countryside is particularly beautiful in spring and fall, when the fields and vineyards are lush and colorful.

San Gimignano is another historic Tuscan village known for its unique skyline of soaring towers and charming medieval center. Like Monteriggioni, San Gimignano is a lovely town to explore on foot, popping into the Collegiata church and local shops, and stopping for a gelato on the main square.