As the bus to San Gimignano winds up the hill side you are presented with your first glimpse of the town’s famous towers poking above the trees in a suitably epic manner. The bus drops you right outside the Porta San Giovanni, the best-preserved gate to the city.
From here follow the crowds of tourists through the gate and up the Via San Giovanni. Shops to either side sell local cheses, meats and wines alongside more obvious tourist fare such as postcards and calendars. This street will deposit you in the
Piazza della Cisterna. This is the real heart of the town, centred on a rustic well, often thick with teenagers sat on its lip eating
gelato. The older and wiser plump for the cafes that ring the piazza. There are towers around the square too – most notably the ‘Devil’s Tower’ to the north. It gained its name when the owner returned from a journey to find that his tower was taller than when he had left it and jumped to the (understandable) conclusion that the Devil himself must have effected some quick alterations in his absence.
From here progress into the
Piazza del Duomo. This square holds two sights that you will not want to miss. To one side is the
Collegiata, austerely plain and Romanesque without, but beautifully decorated within. Opposite is the
Palazzo del Popolo, which holds the Museo Civico and tourist information office (and toilets!). It is here that you can buy cumulative tickets for the various sites in town. It is also attached to the 1311 Torre Grossa, by law the tallest tower in Sam Gimignano. It is also the only tower you can ascend, and provides birds-eye views across the town and surrounding countryside.
If you head west (uphill) from here you will reach the
Rocca, or fortress. Frankly there is not much here. It was pulled down in the mid-16th century on the orders of Cosimo I de Medici. All you are left with are the remains of the wall surrounding a patch of lawn. You can climb steps to the remains of a corner tower though, which gives a good view of the remaining towers within the town itself as you are more or less at roof-top height here.
Returning to the Piazzi you can turm north and wander along the main street to the furthest part of town. The church of
Sant’ Agostino is set up here. It has a quiet little brick courtyard but no signs of life when I visited, though it does hold a Gozzoli fresco cycle of the life of St Augustine.
If you head east from here you will find one of the most enjoyable sectors of the town in my view. Not many tourists seem to make it down the Via di San Gimignano and it is a lot more peaceful. Plus you end up at the
Porta San Jacopo. The San Jacopo church here is decorated with a Templar cross and blue Tunisian dishes set into its early 13th-century stonework. I found myself leaving the town at the gateway here, and continuing by following the path that runs outside the walls on the wetsern edge of town. To your left you are flanked by trees, gardens and vegetable patches. You can re-enter the town at the Porta dei Fonti; otherwise it is a long looping walk back to the next gate, the Porta San Giovanni.
Before you leave, take a moment to check out the shops. One thing they sell here that caught my eye was pre-packaged boxes of local wines in different configurations. Competition keeps the prices low, though they tend to be higher around the Piazza della Cisterna, and cheaper as you near the gates. I actually found the area immediately inside the Porta San Giovanni the cheapest, and ended up buying a box containing two bottles of chianti and a bottle of the local vernaccia for just €10.70.