re: Want to take a trip to Italy - Thoughts on length of stay, cost, and places?

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I'd fly into Milan

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Can be very cheap to fly into Milan at certain times of the year. No reason to stay there, just hop on a train and take off. We only stayed to catch a soccer game.

Florence and Rome are both very close and are a must see. I agree about only one day in Venice (if you even feel like heading that far away). That is what we did and it seemed like enough.