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Italy with a 5 Year Old

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My Husband and I are planning a trip in early June with our 5 year old and could use some itinerary help. We have friends in Milian who we plan to visit for a few days and family in Lisbon Portugal that we will visit as well. We also would like to see Venice and Rome. We plan to fly in to either Rome or Lisbon and then fly home from the other.

We would like to go somewhere between Venice and Rome. We have talked about Florence or Umbira but are totally open to suggestions. We would also like to see the leaning tower of Pisa.

We are considering doing this in a 2-3 week period.

Any suggestions are appreciated.

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