American going to Iran from Riyadh in September 2016

Dear readers,

I hope you can offer some insight into the logistics of my wish, which is to have 2016 be the year that I finally get to Iran after many years of considering the idea. I am an American citizen working in Riyadh, Saudi Arabia, so I am aware that my usual independent travel is likely to be impossible. Saudi Arabia's recent cutting off diplomatic ties with Iran may make a trip this year hard or impossible, though. Though I have easy access to the Iranian embassy in Riyadh, it is currently closed. I will be in the U.S. this summer from around late May to mid-July, so I could attempt the visa process from there, but I don't know if that's advised/possible considering the probable timing of a trip: the first two weeks of September. I should have time off late May to mid-July, which is why I am able to go back to the U.S., so I could theoretically go to Iran then, but I may want to wait for September so I can do some personal things in the summer and experience Iran in slightly colder weather/have it be a treat I experience between bouts of work in Riyadh.

1 What strategy should I adopt for pursuing a visa given my whereabouts now (Riyadh), in the early part of the summer (America), and the last half of the summer (Riyadh)?
2 I have heard and read good things about people using official guides, which is the only option for U.S. citizens, but I have also read that Iran is becoming trendier and "relatively more" independent travel may soon be possible. What are your thoughts on an optimal tour to go with and the pulse of Americans getting to become more independent with trips or having to stick to the status quo (I am male, by the way)?
3 If I have about 17 days off in September, I might use all of them for a trip to Iran. I would appreciate suggestions for 14-17 itineraries for someone who has never been to Iran before. I am not a Muslim, and I do not have emotional ties to figures/places in Iran as would be true for some Muslims, but part of the reason I wish to go to Iran is that I have done quite a bit of traveling/living in Muslim-majority countries in the past five years to become better acquainted with the Muslim world. I generally love things that are unique to each country, the arts, natural beauty, architecture, and many encounters with locals. I am almost always more of a city person than a wilderness person, but I do appreciate nature.

Other questions may surface later, but I think those might get me started for now, especially as I have a fear that I might not even be in a position (due to governments, not anything of my doing) to make this happen this year despite the fact that Iran is #1 on my list of new countries to encounter.

Thanks in advance for feedback.

Hello,

regarding to case three, you asked for, I could suggest an unknown place, Varzaneh, where it has a beautiful sand dune desert, salt lake, wetland, rivers, temples, and citadels... . Special of that regions is dovecotes... . You can read about it more here:

http://wikitravel.org/en/Varzaneh

Thanks for the reply and links.

You might hop over to Dubai for your visa, after your Iranian travel agent has secured your authorization number from the MFA. If you make a special visa run, stay a while, UAE is a big country and there's a lot more to see than just the artificial glitz and bling of Dubai! If not, then it's just a quick flight to Shiraz/Esfahan/Tehran.

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