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Itinerary advice needed! Italy-Greece

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Hi, I am travelling to Italy and greece in the first week of June this year with my family. We haven't seen it before and like everybody else strapped for time, want to do as much as we can.

This is my ambitious plan for now:
Land in Venice-stay 2 nights
Take train to Rome-stay 2 nights (we're not exactly history buffs) or maybe we should do Florence or cinque terre?
Train to Milan onward to lake como for 2-3 nights and then back to Milan
fly onwArd to Greece for a week spent between Athens and santorini.

We can maybe do 1 more night somewhere. Is this itinerary even possible or am I just going to be spending all my time travelling between places? I do realise I'd be better off spending both weeks in Italy, but we'd like to do both countries.

Your comments would be appreciated. Thanks.

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