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Italy in November but from Alaska, what to pack?

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Hi, I'm traveling to Rome, Florence, Venice and Milan next month (November) for two weeks. I live in Alaska and by the time I leave for the trip, the temps in Anchorage will be in the 20's and below, with snow on the ground and winter in full swing. But the temps in Italy will be in the 50's or 60's so it will be a heat wave for me. I also understand it could likely be raining much of the time. Is a light leather jacket appropriate, with a lightweight rain jacket to put over in case it rains? And as for shoes, I was planning on bringing a comfortable pair of black mary jane Naots and merrell mocs. But if it's raining a lot are rain boots recommended? I also have a compact umbrella I plan to bring. I've read that lightweight sweaters are good for November in Italy, but I would be sweltering in Alaska wearing those if it was 60 degrees. I would like to pack as lightly as possible, so any help on what I should pack given where I'm coming from, would be great.

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