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As cited in How to get a visa for Iran, Americans getting a visa to travel to Iran must follow this procedure:

At present the Iranian Foreign Ministry does not allow American passport holders to travel to Iran independently. Americans are required to travel on escorted tours; either as part of a tour group, or a tailor made individual tour. An exact itinerary, to which you must adhere, is compulsory.

I am an American citizen and I was born in America- however, due to both my parent's nationalities and places of birth, I am also a Canadian citizen with a Canadian passport.

If I were to travel to Iran using my Canadian passport, does that mean that I would be free to move about Iran without a tour group & itinerary? Or would I have to organize an itinerary beforehand due to the fact that I am living in the United States?

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Where you live or what other passports you hold is irrelevant. If you apply for your Iranian visa with your Canadian passport, you will enter as a Canadian, not an American.

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I would not want to bet on that. If you hold an American passport, I would bet that Iran considers the conditions for American passport holders apply to you. If you were found to have deliberately disobeyed those conditions - well, lets just say that spying is not something you want to be accused of in Iran. –  DJClayworth Jun 18 '13 at 1:19
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Why would you tell Iran you have an American passport? The Iranian visa application form (iranembassy.org.au/form/visa.pdf) only asks for the nationality of the passport you want the visa for, you can fill it out 100% honestly. (Except maybe the permanent address bit... but plenty of Canadians living the US, so you don't need to lie there either.) –  jpatokal Jun 18 '13 at 5:12
    
Absolutely, you might get away with it. And if you don't, you're am American spy pretending to be Canadian. –  DJClayworth Jun 18 '13 at 13:12
    
You, my friend, have been watching too many spy movies. If you're a legit Canadian citizen with a legit Canadian passport applying for an Iranian visa with your legit Canadian details, you've committed no crime and have nothing to worry about. On the other hand, if you're actually an American diplomat pretending to be a Canadian science fiction movie maker using a passport you got from Ashton Kutcher, you might have cause to be a little nervous! –  jpatokal Jun 18 '13 at 23:16
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Also, here's an Iranian travel agent saying that dual citizens using their non-US passport are "absolutely fine": tripadvisor.co.uk/… –  jpatokal Jun 18 '13 at 23:18

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