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Driving from Siena to Vienna, town to spend the night in along the way?

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My mother (she is only 50) and I will be driving from Siena to Vienna in late February and are looking for a small and charming town to spend the night in along the way. Venice is on the way, but a friend suggested that it would not be worth our time to only spend one night and have less than a full day to spend there.
Thoughts?
Thank you!

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