40km (25 miles) NW of Siena; 57km (35 miles) SW of Florence; 270km (168 miles) NW of Rome
The scene that hits you when you pass through the Porta San Giovanni gate, inside the walls of San Gimignano, and walk the narrow flagstone Via San Giovanni is thoroughly medieval. Okay, so the crossbows, flails, and halberds in shop windows are miniature souvenir versions, and the small Romanesque church facade halfway up the street today hides a modern wine shop. But, if you can mentally block out the racks of postcards, you've got a stage set straight out of the history books.
The center is peppered with the tall medieval towers that have made San Gimignano, "city of the beautiful towers," the poster child for Italian hill towns everywhere. No one can agree how many stone skyscrapers remain -- so many have been chopped down it's a tough call whether they're still officially towers or merely tall, skinny buildings -- but the official tower count the tourist office gives is 14. There were at one time somewhere between 70 and 76 of the things spiking the sky above this little village. The spires started rising in the bad old days of the 1200s, partly to defend against outside invaders but mostly as command centers for San Gimignano's warring families. Several successive waves of the plague that swept through (1348, 1464, and 1631) caused the economy (based on textiles and hosting passing pilgrims) to crumble, and San Gimignano became a provincial backwater. Because there was no impetus for new construction, by the time tourism began picking up in the 19th century, visitors found a preserved medieval village of crumbling towers.
San Gimignano is by far the most popular Tuscan hill town, a day-trip destination for masses of tour buses coming from Siena and Florence. Therefore, the town is best enjoyed in the evening, after the tour buses leave, especially in the off season and on spring nights: The alleyways are empty, and you can wander in the yellow light of street lamps.