Buongiorno,
Instead of looking for small, off the beat towns, I suggest you stay in Siena and then Florence. Florence is about as close as you get to being near the main highway which will take you to Venice.
The drive between Florence and Siena is short - but you can use this to your advantage because it will give you time to visit both towns (definitely an experience to not miss) or you can drive through Chianti for some breath taking views.
Buon Viaggio,
Donna Denise
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