I would choose the ferry route from Turkey Through Greece and into Italy. You are looking at a 1-2 days on the ferry, but if you get off here and there to break it up, it shouldn't be too bad. Bring a blanket or something for the overnights on the ferry.
As for Italy, they have a pretty good train system, so I would just take the trains from city to city. Quite cheap also!!!
Good luck, and keep the questions coming
When an adventure ends you can never go back, never relive it, never hope to feel the same emotion. The secret is to not try and go back but to keep searching for new adventure....