It will be absolutely fine and very easy with the possible exception of the Libya element. I made an identical trip with the exception that I used public transport, however I made this trip before the Arab spring. Even then, getting the Libyan visa was a complex and drawn out process, now I do not know whether it is safe or even possible for a tourist. You could easily take the ferry down to Morocco, travel across as far as Tunis and then get a Ferry up to Italy and this trip will be completely safe and as far as I'm aware will pose no difficulty at all in obtaining visas. However, if you are determined to at the Libyan element then I am sorry to say that I can offer no advise and would suggest you research current conditions in Libya.
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