San Gimignano Loop hike

The San Gimignano walk is tricky, as there are no markings to help you find your way. This route has a lot of subtle turns, and it’s actually quite hard to follow with a text description alone. We suggest you have the GPS file downloaded and/or have a map on your smartphone that shows your position on this route.

Before starting, enjoy some time in San Gimignano. Stop for a cappuccino or a cornetto at one of the many cafés lining the street out of town. If you stand at the bar, a cappuccino is very cheap.

From Piazza della Cisterna take Via S. Matteo north out of town. Continue along this road until you cross SP1 to Via Niccolo Cannicci and then take a quick right on to Via Cepparelli. The walk out of town has amazing views of San Gimignano to the left side with vineyards in foreground.

Continue along this road until it becomes SP127. Stay on SP 127 until you reach a fork and take the road that veers to the right, getting off SP127 (do not take Via Cortennano which is a right turn). Continue on this road for roughly 1 km where you will come upon the Teruzzi Winery. You can get a guided tour of the winery, which includes a fine tasting.

Pass the winery and continue along Localita Casale for roughly 2133ft as it curves to the right and you will once again approach SP127. Walk along the SP 127 for roughly 98ft then turn right onto Via Sant’ Andrea. Follow along this road for 0.9mi as it twists and winds through groves and forests. At this point there is an intersecting road to the right. Continue straight but the road name will change to Localita Montefalconi.

Continue along Localita Montefalconi for roughly 0.9mi. It will wind its way through several BnBs and the lovely Tuscan countryside. Just before the 0.9mi mark you will pass a good place to stop for a bite if it is that time of day – La Grotto di Fulignano. Enjoy a great meal with fantastic views of the Tuscan countryside.

From La Grotto di Fulignano, you will come to a small settlement where Localita Montefalconi will continue curving to the left, but you will take the road to the right at a T – junction. Follow this road for roughly 807ft and then there will be a small dirt path to your right. Go right here and continue along this unnamed road until you reach a T-junction, here turn left. After following this road for 1476ft take a right. This will take you around the side of Geografico Wine Shop, a popular place to buy wines, olive oil, balsamic vinegar and meats.

At the next road take a right and it will bring you to the front of the shop and straight on to SP1, a fairly busy road. Continue along SP1 to The Pietrafitta Wine Shop and then veer to the small road on the right, getting off the busy SP1.

Follow along this road as it hugs the trees and passes olive groves. After about 1 km you will come to a fork in the road, continue hugging the trees to the right and you will curve around the main buildings of the Pietrafitta winery. At the next intersection, go left and then a quick right. Continue along this road until you are once again back on the SP1.

Take a right on the SP1 and then the next right on to Via Vecchia per Poggibonsi (this is across the street from the Ai Vecchi Tempi restaurant). This road will wind past a few restaurants, houses, B&B’s, and eventually back into San Gimignano.

Once you are back in San Gimignano, you can either follow the road back into the small streets of the town, or take the pedestrian staircase that leads to Piazzale Monternaggio and then into San Gimignano via the gate and onto Via San Giovanni. Continue on this road until you are back at the Piazza Della Cisterna, where you can return to Siena on the bus or keep exploring San Gimignano.