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16 nights in Italy but unsure of itinerary and direction of travel

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This is my first post and I hope I am doing it right :-). I need some help with a 16 night itinerary for Italy. My husband and I are mid-forties and travel quite a lot. For this trip we will travel at the end of May through Mid June 2018. We will do open jaw tickets but I have not definitively figured out where to start and where to end yet. As a bit of background; I have been to Italy a few times but he has not. Some of the places on the itinerary will be new to me. We are coming from the US so I believe it is better to start with one of the longer stretches to acclimate. We love walks, history, beautiful vistas, architecture and food. We are not into the night life and minimally interested in museums. So please help me with this:

Arrive Rome- overnight x 4
travel to Positano- overnight x 4 (I have never been to the Amalfi Coast)
travel to Florence - overnight x 2
travel to Cinque Terre- stay in Riomaggiore or Vernazza -overnight x 2 (I have never been to the CT)
travel to Lake Como via Milan- stay in Bellagio -overnight x 2 (I have never been to Lake Como)
travel to Venice -overnight x 2 and leave from Venice.

I am unsure about 2 or 3 nights in CT (I could lose one night in Florence for CT if that's best).
I figure it is best to start with the longest stay and then put the shorter stays on the back end. However, I am concerned that the CT might pale in comparison to the Amalfi if we see the Amalfi first.
Do you think the trip should be done this way? More or less time in an area? Do you think it is better to start in Venice and end in Rome? We would travel by high speed train as much as possible and can rent a car/hire a driver if necessary as well. I am open to all suggestions.

Last year we took a trip through SE Asia where we started in Chiang Mai with 2 nights then 4 nights Bangkok, 2 nights Siem Reap, 2 nights Hanoi, 1 night (overnight cruise) Halong Bay and then 3 nights Ho Chi Minh city. With the exception of Halong Bay we flew between cities then and the pace of travel was just fine for us after the initial day of jet lag in Chiang Mai. I say all that to let you know we aren't strangers to moving around and trying to get the most out of the destination but again, I am open to all suggestions regarding itinerary and direction of travel. Thanks!!

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