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Flight to Florence - layover in Italy or elsewhere

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We are going to Florence to which unfortunately there are no direct flights from NY. The question is: if we pick a flight with the layover outside of Italy - say Charles DE Gaulle or Germany do we have to take our luggage and go through customs? If we pick a flight with a layover such as Rome or Milan would our luggage be transferred and would we avoid customs in the layover city.

We're trying to make the trip as easy as possible.

Also considering flying to Rome and taking a train.

Any thoughts?

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