It should be technically possible to take the ferry from Tasucu (Turkey) to Tripoli in Lebanon, then enter Syria and go to Jordan (from where it is easy), but nobody has entered Syria with a vehicle recently as far as I know. You need to be guided through Syria by a travel agency in order to get a visa. If you ask the agencies about turning up with a vehicle, they will say it is not possible. My gut feeling is that you would get in if you turn up at the border with the vehicle, meet your tour guide and deal with it on the spot. But there is of course the possiblity that you will have to turn around and find another way in.

Also, note that conditions in Syria are pretty bad at the moment, the currency is collapsing thanks to the collapse of the Lebanese banking system, power and fuel supplies are erratic and according to my Syrian friend (who has family still living there), there has been a spike in crime (usually unheard of in Syria).

Alternatives are shipping to Israel from Italy directly (then you will have Israeli stamps, or stamps from Israel's borders with neighbouring countries)

Or going through Iran, take the ferry to UAE and on into Saudi. This will require an organised tour through Iran if you're British or Canadian. Not sure it would be possible at all if you're American.

EO

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EurasiaOverland a memoir of one quarter of a million kilometres by road through all of the Former USSR, Western and Southern Asia.