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Help!!! What to eliminate, what to include in Italy itinerary???

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Hello,
I'm planning my first trip to Italy with hubby for "Big" anniversary trip in May 2014.
Here are the details and tentative plans so far: Flying into Venice, and out of Rome .We have 18 nights. We would like to visit Venice, Florence, Rome, Positano (or another town on Amalfi coast??). We also would like to explore the hilltowns and special places in Tuscany, and perhaps get into Umbria as well. We'd love to see Cinque Terre but that may be unrealistic as I don't want to overdue the plans. We are active, fun loving "fifty somethings."
We enjoy food and wine and plan to rent a car for the Tuscany/ Umbria portion of our trip.
I have two nights booked in Venice ( although I'm thinking we may need 3 to allow so extra time to explore the city) We originally hoped to train to Cinque Terre for 2 nights but it looks like a rather lengthy trip so I thought it simpler to then head to Florence .Any thoughts or experience with that ?
We plan to spend 3 nights in Florence and have chosen a hotel already. From Florence is where I'm struggling.... Do we try to fit in Cinque Terre here or eliminate that and save it for next time? If we did go from Florence does it make sense to take the train north then turn around and head south to home base in Montepulciano? We thought we would stay in, or just outside Montepulciano for 5 nights (tentatively). Instead of Cinque Terre we could add a night to Venice and perhaps one to Florence or perhaps Lucca.
Anyway, after the five nights in Montepulciano we planned to head to Positano or Sorrento. Have not picked a place yet but planned 3 nights .
From there to Rome for our final 3 nights. We have reservations at Marriott Boscolo Palace on points so that is set.
Whew, I hope that is not too confusing!!!
I know that I dont' want to have a car in Venice, Florence, Rome or the Amalfi Coast so thought we could pick it up after our nights in Florence and drop it off in Naples and get a bus, train or driver to take us to Positano. Thoughts???
I feel like i could go on and on with questions but first need to get this itinerary refined.
Thanks so much in advance for any help and insight you all may have.

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