Greece-Turkey-Syria-Jordan by land

Hello everyone,

I'm getting ready for the summer holidays and have booked flight Rome - Damascus, but for some reason even though I have travelled by plane many times I feel it would be better to do it by land this time. Thought I could catch ferry from South of Italy, head to Greece or directly to Turkey, and make my way to Damascus and then Aqaba.
Now I have 40 days so the question is: could I do it in 40 days? Have you ever done this before? would you recommend it?

Big thank you to those who will help me.

From where? One way or no?
I've done this trip (from France) in 5 weeks but returning from Egypt (By ferry but it was in 1993). I thinks it's doable but a little boring as ,with 40 days, you have to take almost the same route for going back.
RR.

sorry, you're right I forgot to mention where my journey would be starting from: I live in Rome, so I could take the ferry from Italy...it's not a one-way but a return. Did you go through Greece, Turkey, Syria, Jordan and you said Egypt in the end? I didn't know there was a ferry from Egypt but it certainly doesn't leave for Italy...

What was your travelling experience like? and was it affordable? I know it would work cheaper by plane (I've found a flight for 470Euro tax included) but that would take me to Damascus and back and I would need to make my way into Jordan anyway.

Any suggestions?

Yes, I've travel through the same countries and it was a fantastic trip and very affordable .
Ferry from Egypt doesn't work since almost 12 years .
Have a nice trip.
RR.

Ferries to Turkey:
A) Ancona - Cesme: http://www.marmaralines.de/iindex.htm
B) Ancona/Bari/Brindisi - Patrasso, Pireo - Rodi, Rodi - Castellorizo, Castellorizo - Kas: http://www.gtp.gr/, http://ferries-turkey.com/turkey-greece/turkey-greece-index-en.html

Bus to Syria:
A) Cesme - Izmir, Izmir - Adana (diversi itinerari), Adana - Aleppo
B) Kas - Antalya, Antalya - Adana, Adana - Aleppo

Cheap flights Adana - Istanbul: http://www.pegasusairlines.com/EN/

I did this trip last fall from Athens to Cairo. The trip took approximately 2 1/2 months overland including 26 days travelling around Egypt. You can do this route easily but you MUST fly back. Who wants to backtrack? Get a one way ticket out of Cairo back to Rome. This has got to be easy and relatively cheap. Check out Egypt Air. They may fly that route. Getting in to Egypt with no return ticket is hassle free. They don't even ask. They didn't ask for onward tickets anywhere along the route. You'll have to get your Syrian visa at home...officially. People report that they do it all the time at the border and save heaps of money by doing so but you never know...you may get denied.
Btw, you don't need 2 1/2 months for the trip but 40 days would really be pushing it.

Rits

May be it's cheaper to fly from Cairo to Athens: http://www.aegeanair.com/