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Travel to Turkey, Syria and Iran

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Our son works in Tehran and we want to use this opportunity to visit Iran while he is there. At the same time we would like to see some of Turkey and the Middle East. We are in our early seventies, in reasonably good shape and don't need to skimp..., but want good value for our money. I don't have access to guide books at the moment (am spending the winter in Mexico), so I am asking my questions here.
First of all this is our 'draft' itinerary. Book a return flight from Toronto to Istanbul in May. Spend a week in Istanbul, then take the train to Aleppo, Syria. Spend some time in Aleppo, then take the train to Damascus. Spend a week in Damascus, then fly to Tehran. Spend two weeks in Iran, then take the train from Tehran back to Istanbul for our flight back home, possibly spending some more time in Turkey. All together we are looking at about 6 weeks.
Here are my questions:
- visas for Turkey and Syria, do we have to get those in Canada?
- visa for Iran: any Canadians applied lately and any idea how long it takes?
- according to 'themaninseat61' the train from Istanbul to Aleppo has not been running for a while and we can only get to Adana (which I believe is at the Syrian border) and from there we can take buses or a taxi to Aleppo, after having spent the night in Adana. Anyone done this recently, is this still the situation? Recommendation for hotel in Adana?
- how much time to spend in Aleppo, would a few days suffice? Any hotel recommendations?
- we do have a contact in Damascus, who will put us up and help with while there, but we wonder if we should go into Jordan as well, when we are so close...
- finally on the train back to Istanbul from Tehran, should we get off some other place to see a bit more of Turkey?

I have posted this on the Turkey forum as well. Thanks in advance for your help!

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