I am going to be in Florence in mid to late September with the opportunity to travel through Tuscany for a few days (right now I'm thinking 3 days, but I could always be swayed to stay a few more). I have some questions...

1. What cities and towns should I consider?
2. Would it be better to choose 1 town and do day trips around the area?
3. Would I need advanced reservations at accommodations?
4. Is there are circular route I could do to end up back in Florence?
5. Are there any local lodging places that specialize in this sort of thing?
6. What else should I be asking???

I'd be happy for any guidance!!