We are considering staying in Tuscany and visiting the hill towns after our booked 7-day tour, based in Montecatini, ends. Prefer not to drive.
Welcome! We spent a wonderful week in Tuscany, using an agriturismo as a home base and visiting Radda, San Gimignano, Volterra, Siena and other hill towns. Our agriturismo was very convenient, just north of Greve.
Two things might affect your plans. First, check to see what will be available then. Some agriturismos have a minimum stay. Secondly, it is hard to ramble around the hill towns without a car to get from one to the other. I found driving in Tuscany to be easy, just be sure to obey the speed limit, especially near towns. Also cars are restricted in the center of hill towns, but there's plenty of parking just outside the restricted ZTL area. ZTLs are well marked and it is easy to avoid driving in and getting fined.
If you don't want to drive, your best bet may be to stay in Siena or Florence and take day trips with bus tours. Have a great trip! Mid-October will be a nice time to be in Tuscany.