This walk explores San Gimignano’s medieval streets, towers, and squares, with stops at historic churches, scenic viewpoints, local favorites, and, wht some describe as the world’s best gelato.

Via San Giovanni

From the gate, we follow Via San Giovanni, the town’s main street leading toward the historic center. This lively stretch is lined with artisan shops, wine boutiques, and cafés, making it a good place to browse for local products like saffron, Vernaccia di San Gimignano wine, and hand-painted ceramics. The street’s architecture reflects the town’s medieval prosperity, with stone façades and arched doorways that once belonged to wealthy merchant families. It’s also a convenient spot to grab a coffee or snack before continuing.

Piazza della Cisterna

Next, we arrive at Piazza della Cisterna, one of San Gimignano’s most distinctive squares. Its triangular shape and central well date back to the 13th century, when the piazza served as a hub for markets and public gatherings. Surrounded by medieval towers and elegant palazzi, it remains a focal point for visitors today. The square is also home to several well-known gelaterias, making it a popular stop for a break. From here, you can see why San Gimignano is called the “town of towers”—many of the originals still dominate the skyline.

Piazza del Duomo

From here, we make our way to Piazza del Duomo, a quieter square that serves as the religious and civic heart of San Gimignano. The piazza is framed by important buildings, including the Collegiata di Santa Maria Assunta (the Duomo), Palazzo Comunale, and several medieval towers such as Torre Chigi. This is a good place to pause and take in the contrast between the town’s civic and religious architecture. If time allows, we’ll step inside the Duomo next to see its remarkable frescoes.

Palazzo Comunale & Torre Grossa

Next, we visit the Palazzo Comunale, the historic town hall, and climb Torre Grossa, the tallest tower in San Gimignano at 177 feet. Built in the late 13th century, the palazzo houses a small civic museum with frescoes and period furnishings. The real draw, however, is the tower climb—on a clear day, the panoramic views of the Tuscan countryside are unforgettable. Admission is about €9 and includes access to the museum and tower. Don’t miss the Loggia del Comune, an open arcade at the base of the building that once hosted public meetings.

Parco della Rocca

Backtrack a bit and walk into the Parco della Rocca, a peaceful park built on the site of a 14th-century Montestaffoli Fortress. The original structure was largely dismantled in the 16th century, but the elevated position remains, offering sweeping views of the surrounding hills and olive groves. Today, the park is a quiet place to rest, with benches shaded by trees and occasional art installations. It’s a good spot to take a break before we head to our next church.  We can walk through here to our next destination. 

Chiesa di San Lorenzo in Ponte

Head south along Via San Matteo, one of San Gimignano’s most authentic streets. This quieter route is lined with stone houses, small artisan shops, and glimpses of daily life that feel far removed from the busier main street. As we continue, watch for Via Capassi on your left—this is where you’ll find public restrooms, a convenient stop before our final church visit. Just ahead is the Chiesa di San Lorenzo in Ponte, a small Romanesque building with simple architecture and a few surviving frescoes. Though modest compared to the Duomo or Sant’Agostino, it reflects the town’s layered history and the role of smaller parish churches in community life. After a quick visit, we’ll make our way back to the main square.