Day Trip to San Gimignano & Monteriggioni in Tuscany, Siena

Enjoy a day exploring the scenic countryside and picturesque villages north of Siena. Start with a leisurely walk around San Gimignano, a quintessentially Tuscan town comprised of medieval buildings perched atop one of the region’s iconic hills. Located in the Elsa Valley, San Gimignano is most famous for the 13th-century plazas, churches, and stone towers dominating the skyline. It's for these reasons that the entire town is a UNESCO World Heritage Site.

Walk along the ancient Via Francigena (the ancient pilgrimage road connecting to Rome). Your route will lead you through the town from Porta San Giovanni to Porta San Matteo, passing through Piazza della Cisterna, a grand square surrounded by the Palace of the Podestà, the Salvucci towers, and Piazza Duomo. Eventually, you'll reach the top of the town and enjoy amazing panoramic views from the Church of Saint Augustine.

You can also visit local craft shops and one of San Gimignano's famous gelaterias, which have rightly earned a reputation for producing some of the best gelato flavors in the world. Finally, climb the Torre Grossa and admire the amazing views across the vineyards and medieval city center.

The secret to a day trip to San Gimignano is arriving before or after the tour buses! San Gimignano is so much more than the one touristy main street, but most people don't have the time to really explore. 

After leaving San Gimignano, make your way to the impressive medieval fortress of Monteriggioni. The intact castle walls surround this town perched on a hillside and are a sight to behold! Take in the views, have a coffee, and enjoy wandering around the porticos and piazzas in the charming historic center.

Read more about unique and interesting experiences in Tuscany.