San Gimignano - The Italian Manhattan in Tuscany
Despite the catchy headline, San Gimignano has little in common with the Manhattan that first comes to mind - besides the historic "skyscrapers" and impressive skyline. It is actually quite the opposite, with is city center built in the Middle Ages, little restaurants and amazing Italian gelato. It has several museums (if you are into wine and/or the history of torture), art galleries, and speciality food stores where you can sample and buy local produce.
Gelato and medieval architecture
Around the Piazza della Cisterna (the square with the fountain in the middle) there are gelato parlors lined up, competing for awards, and bragging about selling the best gelato in the world. I suggest taking some time and getting a scoop from every shop, just to make sure :)
When you're in Tuscany, you will not want to miss out on a visit to san Gimignano. You can see the little medieval town from afar: the 14 towers are unusually high for the area, and tell stories of the Middle Ages. The roads are narrow and inside of the city walls mostly exclusive to pedestrians. The town is also known for its Gourmet scene and has some local specialities, such as olive oil, white wine (Vernaccia), sausage from wild boar, and pastry.