There are many charming places to visit in the Province of Siena. If you have limited time, the city of Siena is the highlight, and you can easily take 3-5 days to see all the sights there if you so desire. However, if you have more than a few days, make sure to go to San Gimignano, if nowhere else. It's much smaller in area and population than Siena and, with its towers and panoramic view over the countryside, gives the visitor a different experience of a walled Medieval city. Also, because of its small area, a reasonably able bodied person can walk from one end of San Gimignano to the other in 20 minutes, and while it has fewer and smaller attractions than Siena, they are of great quality. Pienza is of special interest to fans of Gothic architecture, because it was completely redesigned as a Gothic village in honor of native son Pope Pius II in the 15th century. If a beautiful rustic monastery with frescoes by Michelangelo's teacher appeals to you, go to the Abbey of Monte Oliveto Maggiore in the tiny village of Chiusure.
It can be very difficult finding a good restaurant open between the hours of about 14:00 to 19:00.
Vegetarians and vegans should have no problem eating in Siena as staff at Italian restaurants tend to be very accommodating. Try ribollita, a regional specialty vegetable soup. 100 percent vegan and delicious. Pizza in Italy (and authentic Italian restaurants elsewhere) has no dairy products or eggs in the dough.
This is Chianti wine country. You will have no trouble finding well-priced Chianti wines in supermercati or trattorie.
Florence - short bus or train journey from Siena.
Rome - Possible day trip to get a glimpse of Italy's capital. Bus or train from Siena.