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Family of 4 - Switzerland & Italy - First week of June 2014 (12-15 days)

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I know its far but due to certain circumstances I need to do my bookings now so really appreciate everyone's help in advance!

I have the option of starting in Zurich and end in Rome/Naples or vice-a-versa.

1) What would you suggest start north or start south.
2) Since almost 3 adults and 1 toddler, would driving be economical?
3) If I have 12 to 15 days (could stretch to 17/18 if necessary), what could be a good itinerary? I am thinking Naples, Rome, Florence, Venice (part at airport), Milan (return car) (train into Switzerland) (rent car again) Place to visit in Switzerland (return car in Zurich) Fly back from Zurich.

Please help :)

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