Planning trip to Italy (from the U.S: Florida) in September

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My wife and I are planning a trip to Italy which consists of the following cities for about 13 - 14 days.

1. Milan - still debating if to go

2. Venice

3. Rome

4. Florence

5. Positano - Would like to leave this for last to decompress as it looks very beach centric.

About how much days are recommended per city and what are some of the best options to travel into and out of italy from Florida (Miami specifically).

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