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Best of Tuscany for a 10 days trip

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Dear Fodorers,
We might be considering a trip to Tuscany for ten days mid of May. We are a couple in our early forties with a 3 years old baby boy.
My question is a typical one but I really need your input to make up my mind.
Can you give me the names of the top 10 villages/towns to see in Tuscany? something like the must sees? I know it depends on our base but this is not yet chosen. Suggestions are welcome but we usually like to stay in 4-5 star modern hotels and in an area that has shops, supermarkets and pharmacies just in case (you know we have a small child).
We usually chose one base and rent a car to drive to villages and towns.
We like scenery and to wonder in attractive towns with cobbled streets (prefer elevated ones though) and nice souvenir shops, we do not drink so wine is not the criteria to base our choices on but love to see vinyards as a background. We also like to eat well and drink the delicious cappuccino!
Can you give us some suggestions and the name of the main piazza or area for each please.
Also for those who wish to suggest a base for our trip, can you suggest a good modern neat hotels?
Many thanks in advance.

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