If you want to incorporate wine tasting and cooking classes, then I would highly suggest Siena. While it is a major town, it actually conserves a quaint feel to it, especially if you stay within the historical center and close to the walls, you can also enjoy views of the countryside!
In Siena, we've stayed at various spots across town and enjoyed every single time we've stayed there. You can take wine tours and cooking classes in town, as well as join in with group tours to go out into the surrounding wine areas. This way you can experience both sides, but the main thing, is that Siena does not feel big at all, despite the crowds during the summer. So if you haven't yet booked a time period, I would recommend coming either late spring/early summer or late summer/early fall. There are still lots of people around but not super crowded in the day time. Even in the summer, when we've stayed in Siena, the crowds leave by evening and it is very enjoyable to be in town for dinner and after.