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1st trip to Italy - advice?

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I'm trying to plan a trip (10 days?) to Tuscany & Rome in early October to visit my neice who will be studying abroad in Florence. The majority of my time will be spent in Tuscany with a few days in Rome, perhaps. I was thinking about staying somewhere in the countryside (villa?) as a base and doing day trips but wasn't sure if a day in some of the places I hope to visit will be enough. Looking for itinerary ideas. I am just starting my research but hope to see:

Florence (2 or 3 days?)
Pisa
Siena
Chianti
Montepulciano
Rome (2 or 3 days?)

Other must visit places in addition/instead of the above?
Suggested itinerary/order to visit these places?
Ideas for a visit to the coast in this region?
Do you recommend having a base and day trips or moving around and staying in multiple towns?

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