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Itinerary Plea - 14 nights, first trip

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I'm planning our first trip to Italy - "our" meaning myself, 13 yr old son and possibly husband. Dates are firm - mid March, and coming from one night in Paris (quick dr. appt.), flying from Paris to save time. 14 nights sounds like a decent amount of time, until you look at all the places you want to see! Priorities are food, neighborhoods, atmosphere with a reasonable amount of art and churches. Son has way more interest in Italian food than Italian art, and I don't want to make this a Bataan death march of churches.

My thoughts so far are:
Fly into Venice. 3 nights.
Train to Florence. 2 nights (more to get a taste for it than to see every single thing; hence only 2 nts.)
Train out of Florence, pick up car someplace manageable. Would like to see Siena, Montalcino, not sure what else. 4 nights roaming around?
Then to Rome - drive part way, hop on a train? 5 nights Rome?

I'm somewhat bothered by only going to the obvious places, but since this is a first trip, I think perhaps this approach works best? I skipped Cinque Terre because we are not hikers. At all. We love trains and boats, though. I'm sad to miss Amalfi, but am thinking that's a second trip - Amalfi, Puglia, Sicily, etc.

Would greatly appreciate input on all of the above - am I on the right track, wrong track, too much time, not enough, best way to attack Tuscany, etc. I find we have the best time when we wander around and only do one or two monuments/museums/cultural things per day. In Paris, we like sitting in cafes and watching all the dogs go by, and in Scotland we loved driving around Skye, baaing at the sheep! Sad, but true.

Thank you in advance for any advice you can offer. Realize the weather might not be great, but will do almost anything to avoid crowds and oppressive heat.

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