Siena, capital of the Chianti country, is a great place, Eliza ... much smaller and more walkable than Florence, but still big enough to have a lot of variety. Lots of little towns throughout Chianti (Radda, for instance) are almost invariably pleasant, and it's hard to find a trattoria anywhere in Tuscany that doesn't have great food.
In Umbria, Perugia, the capital, is worth a look. A real centerpiece for art, and not an overly large city. Assisi gets a lot of tourists, and Torgiano is almost entirely dominated by the huge Lungarotti winery. The winery/hotel restaurant, Tre Scalini (I think) isn't bad for upscale dining.
Little villages around Lake Trasimeno can also be interesting to visit and maybe enjoy outdoor dining with fresh fish ...
Eliza W wrote:So, work might be taking my family to Tuscany for a few months next summer. We'll be in Florence for just over a month, but then we want to take another couple of weeks for the family and rent a place in a smaller (and hopefully less hot and humid) town.
I'm looking for someplace with great small restaurants, bakeries, gelaterias, and food shops. It doesn't have to be the place with the most tourist attractions or services for visitors. We want to walk, eat, and play with the kids. Any suggestions?