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Grandparents travelling with 11 yr old grandson to Italy -itinerary ideas

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We have 2 weeks in Italy - have planned 5 nights in Rome then up to FLorence area to see Pisa and Lucca and then on to Venice for 4 nights. We finally fly out of Milan .
1, What would be the best routing and # of days for the time between Rome and Venice.
2. What might be unique or of interest for 11 yr old boy. Has anyone taken the Glidiator tour in Rome?
3.Would there be a stopover of interest on the Venice to Milan trip.
4. Any very reasonable accomodations (a joke in Italy) would be helpful.
Thanks

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