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Opinion Please

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I am traveling with my husband and another couple to Italy for 2 weeks in May. Our itineray is as follows:
Rome - 3 nights
Positano - 3 nights
Cortona area - 3 nights
Florence area - 2 nights

We will rent a car as we depart Rome and return it in Florence.

The other couple we are traveling with want to take the train to Venice for 2 nights before heading to Milan for one night and flight back to US. My husband and I were thinking of that being too far and would rather be in Pisa/Lucca for one night and Cinque Terre for 2 nights before our last night at Milan airport. Is it a mistake to wait and decide how we feel at the end of the trip to make a decision? Wil hotels be a problem in CT to book mid-week in May?

Any opinions on Pisa/Lucca/CT vs. Venice?

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