I can't help you with the weather predictions, but I'm planning a similar trip, leaving slightly earlier and taking a bit longer (India in January, hitting Turkey in maybe May, possibly a bit of Middle East if I've got time). It sounds as though you'll catch up and overtake me - look forward to seeing you on the road!
I'm interested in finding out about a ferry that allegedly runs Israel-Italy. Have you ever heard of that, Pietro? Perhaps I'll ask about it in the Middle East Forum.