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Italy: North to South or South to North?

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I'm planning a three-week trip to Italy starting on either September 14 or 21st.

I am debating whether to start in the North (either Venice or Milan) and end in Rome or vice versa.

A friend recommended North to South as that way I will maximize the chance of having warmer whether when I am in the north.

However, the dates I am looking at appear to be around Milan's Fashion Week, which is making the hotel prices very high in both Milan and Venice.

I have enough miles for a free flight, so I'm not concerned about flight price.

Any advice?

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