Istanbul to Addis - Group Travel

This started out as an idea for a trip from Egypt, through Israel and into Turkey. But then I did some research, and for Americans it makes more sense to go the other way. Something about countries not letting you in once you have an Israeli stamp in your passport. But I also wanted to make a trip from Egypt to Kenya, via Ethiopia and Uganda. So, I don't know if this is going to be two shorter trips, or one massive one. I'm still in the early planning stages, and a lot will depend on the cost.

I have a decent amount of experience as a backpack/shoestring traveller, and I haven't had problems picking up enough of a language to get by in the past. But Arabic, Hebrew, and Amharic are not on the list of languages I speak. And I've never been to Africa, or the middle east.

I am looking for ideas, thoughts, advice, etc. If you've done any part of this trip or a similar one, I'd particularly like your advice re: how much time to allot to various countries, and anything else you think I need to know. I think I had the original thought for the Cairo to Luxor portion of the trip plotted out at 6 weeks.

If this sounds interesting or you want to join me for part or all of my trip, let me know.

I'm female, 34, American, blah blah blah.

Istanbul to Addis