Sounds brilliant, and 50 miles a day with a couple of weeks to look around sounds pretty sensible to me. Not sure I agree with imi about the route, though of course it is all a matter of taste. I'd be inclined to go across France and enter italy via the Alps. As for the route from Rome to Israel, it depends on how much time you have. If there's plenty, I'd just ride it - going north and taking in Venice before turning south through the Balkans. If time is pressing, then I agree the ferry from Ancona is a good bet - but I'd get off at Split and cycle the rest. I haven't done ths route myself, but Bosnia, Montenegro, Macedonia are supposed to be spectacular.