Favorite Tuscan town/village and why

Pienza. Beautiful and lots of good restaurants. Also, not too hilly.

Montepulciano….wow

Cortona - so many beautiful works of art, friendly people, spectacular views, wonderful restaurants.... I could go on and on!

Monteriggioni.

Because it's very small and when you enter inside the walls it is like being thrown back to the middle ages, with the addition of a good wine tasting room near the main piazza.

Also, being near the freeway exit, it is also the best place to have a base to visit the entire province of Siena (and beyond)

Pienza for same reasons Becky has listed
Also- the views!

Loved Montepulciano as well but it's so steep we won't stay there again.

I'm going to assume you mean places that are not obvious or large, and that you mean places we've stayed a few nights in, so I'll say Tuscania because it has some churches, museums, and restaurants we liked a lot, and Pontremoli because of its bridges, medieval streets, stele museum, good places to eat, and closeness to other interesting towns within short driving distances.

Also, on our latest trip last September, when other towns we stayed in were packed with tourists (Tarquinia, Volterra, Massa Marittima, Pisa, etc), these two were very peaceful.

Lucca! i know it might be a bit too big for the criteria, but we love Lucca. With the walls that you can bike or walk, the churches, all the wonderful restaurants.

Lucca and Montepulciano.

I love the views in the Val d’Orcia so I agree with Pienza for that reason, but Montalcino is my favorite in this area. In the Chianti area I do also love the views from Panzano.