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Tuscany where to stay ???

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We now have 5 nights to spend in the Tuscany area .We were going to spend 4 nights in a villa in montepulciano and have added a night to be able to return the car on a Monday.(closed Sundays).We had planned to travel back north a couple of times to see, siena,Pisa, etc. .My question is should we base in sienna for two nights and then move south to montepulciano for three???We will be coming from lake como area.
thanks for any input.

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