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Cruise/Land Combo Questions

I am looking at taking a repositioning cruise in September that begins in Kiel, Germany and ends nine days later in Genoa, Italy. I want to fly into the closest airport to Kiel, which appears to be Hamburg, and after a couple of days in the Cinque Terere fly out of Milan back to Dallas. Has anyone ever done something like this before and is it a trip that would be enjoyable if done alone? Do you know what transportation is available is available from Hamburg to the port in Kiel? Since I'm flying out of Milan, what can I squeeze into a day there. Thank you. Jim PS I have never taken a cruise before. Any tips?

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