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Please help with some logistic questions - Italy

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Hi, back to my planning for our trip in May. We will have 2 weeks and we mainly want to go to the lakes, southern tuscany and Rome.

We do not have our air tickets yet but are planning to fly into Milan and out of Rome.

I need help with a few logisitic questions:
1. We want to drop by Milan for a day to see the Duomo. Should we do it upon arrival or should we do it on the way from the lakes to southern tuscany?
2. What is the best way to travel from the lakes to southern tuscany? We'll rent a car at some point. Where should we pick it up?
3. We want to see Volterra as a day trip. Should we do it en route from the lakes to southern tuscany or as a day trip from our base in southern tuscany?

Thanks in advance for your contributions!

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