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Italy in late June: Start North or South?

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We are taking the family to Italy in late June for about three weeks. Checked flight prices and it seems to make no difference if we fly into Milan and out of Naples or vice versa. Is there an advantage to doing it one way vs. another? We are going to travel by train and at a minimum go to Venice, Rome, Napoli and Pompeii. Yes, I know I left Florence off the list, we might just skip it as we don't like it but probably will want to go to Assisi etc. on our way across the country. We don't really mind heat so trying to escape hotter temps South as the summer progresses isn't that important, but avoiding crowds would be (although I know that's going to be impossible). So does it make a difference which end you start at?

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