San Gimignano Walking Tour

The medieval plazas of San Gimignano
Visit San Gimignano, one of the best-preserved medieval towns in Italy. The historic village sits atop one of Tuscany’s iconic hills that dot the countryside in the Elsa Valley, an area rich in cypresses, vineyards, and olive groves. The region produces the popular Vernaccia di San Gimignano white wine with floral and fruity notes. However, San Gimignano is most famous for the 13th-century walls that encircle its medieval center. With architecturally rich plazas, churches, and stone towers dominating the skyline, the town earned its status as a UNESCO World Heritage Site.

A guide will take you along the main street, Via San Giovanni, where pilgrims and merchants once passed through as part of the Via Francigena route. First, visit Piazza del Duomo's main square, a religious and political center that houses the Town Hall and the Torre Grossa. Then walk to the green “hearth” of the medieval town, the Poggio of Montestaffoli, where you’ll find the Fortress. 

After seeing the sites, enjoy tasting some of the town’s beloved products, such as saffron, Vernaccia wine, and gelato. San Gimignano has many famous gelaterias, with several earning the reputation as one of the best gelatos in the world!

Read more about unique and interesting activities in Tuscany.

Itineraries with San Gimignano Walking Tour

Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days

Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.

Tuscany Self-Drive Tour - 7 Days

Explore Tuscany's incredible art and history on this itinerary. Start your trip in Florence, where world-famous works by Michelangelo, da Vinci, and others dominate the art scene. On a self-drive tour, explore the Tuscan countryside to see 13th-century churches in Siena and try the renowned Chianti wine. Visit the leaning tower of Pisa and relax on the beaches of Cinque Terre before ending your trip back in Florence.

Exploring Italian Wines in Tuscany and Cinque Terre - 5 Days

Indulge your taste buds on this Tuscan tour, visiting beautiful vineyards and medieval towns like Siena, Volterra, and San Gimignano, where you'll enjoy the flavors of the region with wine tastings and traditional, locally-sourced cuisine. Explore ancient cobblestone streets and monuments, enjoy the old Cypress trees of Bolgheri, and sleep soundly in your cozy farmhouse accommodation. End your trip on the rocky coast of Cinque Terre where you'll enjoy more wine and regional foods, plus one last stop at the Leaning Tower of Pisa.

Explore Tuscany: Florence, Siena, & Montepulciano - 10 Days

This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.

Via Francigena: San Miniato, San Gimignano, & Siena - 5 Days

In 990 BCE, the Archbishop of Canterbury traveled from England to Rome to meet with the Pope. He wrote a detailed diary of the 80 stages of his journey through the United Kingdom, France, and Italy, and this path is now known at the Via Francigena (the Francigena Way), a path for religious pilgrims from Canterbury to Rome. The trail travels through Tuscany, and you can experience it on this five-day itinerary that winds through the Tuscan countryside.