WE are driving to the Dolomites in October. I've wanted to go ever since my grandmother went and brought back a tourist book - that was over 30 years ago! I can't wait. It would be a good starting or finishing point.
I have family in liguria and have visited the Cinque Terre, Lerici, Santa Margharita, Via Reggio - all beautiful!! And the most amazing seafood and gelato and of course the Ligurians are famous for focaccia and pesto. If you do go - you must also find and try 'farinata' is is a giant crepe made of chickpea flour. They are huge - you just buy and piece and pay by weight.
If you do Toscany - besides Florence, Pisa I would recommend Lucca, San Gimignano (a bit touristy but very pretty) and Sienna. If you like red wine - the village of Montalcino is famous for it!
Great!! Now I want to go!!