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12 Days trip to Italy

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I am new on Fodor's and I've been getting a mild head ache from trying to sort through all the recommendations regarding Tuscany.
I would love it if you could give me your opinion on my plans and let me know what tips you might have for me.

We're planning to stay in Florence and tour the city & Pisa for 4 days, after this the plan is to drive down to Rome.
I have accommodated 4 days of driving in Tuscany when we want to stop in Siena, Volterra, Orvieto, Montepulciano and other locations along the way for wine tasting and enjoying the good food of Tuscany.
We have also accommodated for 4 days in Rome to enjoy the sites there.

At this point i would need your opinion on 2 questions:
1. Is 4 days driving through Tuscany too long? This is our first time in Tuscany..
2. I am thinking of booking the il Riccio in Montepulciano and driving to other Tuscany locations from there.
Does this makes sense or do you have any other ideas?

Thanks!!!

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