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Italy Itinerary - too much?

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My husband and I are planning our first trip to Italy. We have only about 5-6 nights in the country. I am wondering if this is too aggressive of a plan. We dont want to miss a minute, and are ok with a busy schedule. Just curious if this is doable!

Things that we are most looking forward to; wandering, eating, drinking wine,

- Fly from Miami to Milan, arrive at 10am and take a train to Bologna.
- Spend all day + 1 night in Bolonga
- First thing in the morning take a train to Florence
-Spend all day +1 night in Florence
-Hire a car service to take us around Tuscany, spend 2 nights in Tuscany, possibly Sienna
-Spend 1 night + 1 day in Florence
-Take night train to Milan, spend all of the last day in Milan before flight leaves at 6pm

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