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Italy-Greek Isles Cruise in December

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I like cool weather-in fact the idea of walking around Greece and Italy and summer sounds like hell to me.
Has anyone done a cruise in December? We are working with a teacher's vacation schedule-so could start around Dec 19th and would have to be finished by about Jan 4. Will fly from USA and would like to do a round trip flight into and or of same airport in Greece or Italy.
Any recommendations or experience with this?

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