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Help with Ambitious 12 Day Italy Itinerary

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Hi Folks-
I am planning a trip to Italy for my family of five (3 kids ages 20,18 and almost 16))- June 22-July 4/5, 2016. My oldest will be in Florence through 6-25-16 on a school abroad program. She will travel to Rome as a school group while she is studying there. SO.... I am thinking that we will start in Rome before we meet her, and head north to join her Florence for a couple of days, so that she can show us around. We are an active group and have traveled within the US and to Mexico quite a bit, but never to Europe. My husband is well traveled (been to Italy as well) and I have been a few places in Europe (not Italy). I am thinking that we will spend most of out time seeing the countryside and tasting the culture, hitting the major sites. I don't think that my group will want to do many museums, although we want to see and participate in the most major sites in each location. I am looking for help in deciding if my days in each location and travel schedule is doable, so that we are not running ragged, but so that we can see as much as possible. You will see that I don't understand the train system very well..

Here is my potential itinerary:

Fly from SFO to Rome on 6/22, arrive 23rd
6/23-24- Rome
6/25- Train to in am to Florence to meet my oldest daughter
6/25-6/27 Florence (day to trip to Sienna or Pisa?)
6/28 - train in am from Florence to Venice
6/28- Venice
6/29- train in afternoon fro Venice to area around Cinque Terre (I assume the train runs here from Venice?)
( we can skip this leg if too ambitious!!)
6/29-6/30- Cinque Terre
7/1- train to Positano
7/1-7/3: Positano
7/2 day trip to Capri by Ferry
7/3 train to Naples to stay one evening
7/4 fly out of Naples back to SFO
7/4 Fly out of Naples on 7/4

I can flip the order of any of this - but I need to do Rome before going to Florence and I have to meet my daughter on 6/25! Suggestions? :-)

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