It was great! People are really friendly, mostly you can find someone who speaks English in any given situation, and it's pretty cheap - I'd highly recommend going. People often stopped us on the street just to say "Thanks for visiting Iran"! We just had a two week visa, original plan was to take the train from Istanbul - Tehran. Alas we could only buy tickets in person and they were sold out (lots of Iranians holiday in Istanbul before Ramadam). So instead we flew Istanbul - Tehran. Spent a few days in Tehran, then Isfahan (our favourite city there, the bazaar and square are just beautiful), Yazd (amazing mud architecture) and Shiraz (best spot to visit Persepolis from), then flew on to Mumbai.
Hasslewise: I was traveling with my partner, she had to wear the hijab (hair covering) at all times while outdoors which was a bit of a challenge (try keeping it on with the wind blowing out of the metro in Tehran!). People are very accommodating though, a huddle of women would sometimes form around her to set things right if it was slipping off! This was exacerbated by the time of year (midsummer), you'd be better going sometime cooler. Only other thing I can think of is that the banking system is totally cut off from outside (no ATMs which accept foreign cards, very few places accept western credit cards), so you need to carry in as much cash as you need for the trip. Definitely intending to go back in the future with more time on our hands - there's just endless places to see and visit - it truly was a unique experience.
I live in a predominately Persian neighbourhood in Toronto (Canada) and I'm always told to visit Iran. It's apparently remarkably cheap & the people are very, very friendly. My biggest reservations about visiting Iran was the fact that crossing into the US becomes a bigger ordeal than usual. CBP becomes very inquisitive as to why you went to Iran etc.
I actually passed through the US a few months later (on the same trip - stayed with a friend in SF for a few days between Bangkok and Buenos Aires), the CBP were indeed inquisitive, but nothing beyond some simple questions about where we'd stayed and why we were there. All pretty friendly and non-confrontational. I was in the US again on the same passport a few weeks ago, the guy took a good flick over the visas (and Iranian visa is huge and very obvious), but no questions asked!
