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Italy - 14 day trip - First Visit - Need Help

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I am visiting Italy with a friend in October, first visit for both of us.
We have 14 full days altogether (not including travel days).
This is what we have planned so far, using some tips from fellow fodorites.
Fly into Venice, spend 2 days.
Then possibly take a train from Venice to Verona, then to Cinque Terre, then to Pisa enroute to Florence. How much time would we need for this? Is there a train?
Spend 2 days in Florence. Then from Florence, take day trips or bus or get a tour to Siena, Arezzo, Perugia, Assisi, Umbria (or some of these towns)? How much of this area can one cover in a day? Should we be staying in Siena?
I was thinking we could possibly visit some of these places on our way to Rome. We would prefer not to rent a car - is this doable?.
Spend 3-4 days in Rome (is this enough?).
From Rome, then travel down to Pompeii, Salerno, Isle of Capri.
Then back to Rome to fly home from there.
What are the logistics of doing a trip like this. Should we be doing EITHER Cinque Terre OR Capri/Almalfi and if so, which should we choose? I read in another post that it is the rainy season in CT in October. Looking forward to your comments.

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