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I chose to travel overland to Iraq, or Iraqi Kurdistan to be specific, starting my long journey from the city of Aleppo, Syria. And first, I will say that just as traveling to Iraq in general is not for everyone, neither is embarking on the overland adventure to get there.
View Syria to Iraq Overland in a larger map. Buses depart regularly from both Aleppo 5. I took a night bus from Aleppo and arrived in Qamishli at 6am. On a side note, you can expect to encounter checkpoints en route to Qamishli, and chances are, the soldiers that question you will then phone ahead and inform the secret police in Qamishli of your arrival. Very few foreigners visit this town and due to some issues with a possible American spy a few years back, the town is a bit on edge.
When my bus arrived at the bus station, a driver appeared out of nowhere, asked me if I was Mr Derek Earl and then proceeded to drive me to a hotel to rest for two hours until the border opened.
At the hotel, the manager began asking me an odd collection of personal questions, and eventually admitted that he was instructed to do so by the secret police. It was nothing frightening at all, simply a bit odd. The Turkish side was quite different. Tell them your destination is simply IRAQ unless you want to be subjected to one angry immigration officer screaming with spit flying at you for a few minutes.
There are only a limited number of taxis that are properly licensed to make this trip and most of them head off early in the morning, stay in Iraq for the night and return the next day. Of course, once you do have a taxi and driver lined up, the next step is finding more passengers to split the cost with you.