Around San Gimignano 10.4 km

This hike takes you through and around San Gimignano and offers great views of the medieval city with the towers across a typical Tuscan scenery with cypresses, olive groves and vineyards. The hike is mostly on white gravel roads (strade bianche), and not difficult.
The hike starts at the Bagnaia (P3/4) parking lot on the north side of town. You walk up to the city walls and then to the Chiesa di Sant'Agostino and then on to the city gate at the Via San Matteo. You walk along the Via San Matteo towards the center, then turn right and end up at the Piazza delle Erbe, just off Piazza del Duomo. You then walk up to the fortress Rocca di Montestaffoli, where there is a tower with good views of the town and the countryside. From here you walk back towards the Piazza del Duomo. Just before getting to the square, I climbed the Torre Grossa inside the Museum Palazzo Communale. The view on top is great, but you need to pay a fee which also gives access to the museum (no ticket available to only climb the tower). You exit the museum on the Piazza del Duomo. Via Piazza Cisterna you make a small detour to a viewpoint, and then walk along the Via San Giovanni to the Porta San Giovanni. You exit the town via the old road to Poggibonsi (Via Vecchia per Poggibonsi). This gravel road takes you about 1.9 km from the town with occasional great views towards San Gimignano. You then end up on the new road to Poggibonsi, which you follow for almost 300 m before going up the hill quite steeply on another gravel road. After climbing the hill you follow for 4.6 km a broad gravel road which slightly undulates on the crest of hills with great views across a valley towards San Gimignano and of the surrounding Tuscan countryside. This gravel road takes you all the way to the SP127. You follow a small track beside the asphalt road for 360 m and walk back the rest of the track on the SP127 and another asphalt road for about 1 km until you get back to the parking lot.
You will only find something to eat and drink in San Gimignano.