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Backpacking the Axis of Evil
Some people look at the US State Department travel warnings as a guideline of countries to stay away from. If you consider Thailand, etc overrated by the "nomadic" set, why not look the other direction and see what countries aren't considered tourist hotspots?
After doing the Trans-Siberian/Trans-Mongolian railway two years ago, I figured why not take another epic train trip? And epic train trips demand epic destinations that no one goes to on their vacation. Why not Iran? Sure, Iran and the US aren't too friendly right now, but that's part of the appeal. Anyone can backpack through Europe or do a "round the world" trip, but why not go into somewhere different?
As an American citizen, there are a whole host of issues: getting an independent visa is practically impossible, and once you're there, your credit cards and ATM cards won't work either due to treasury restrictions. And on the way back, US Immigration might not take too kindly to me going there. Either way, it should be quite exciting.
The train seems like the most interesting way to get into Iran. After consulting with Seat 61, the immensely helpful train website, there's a train that leaves from Istanbul to Tehran once a week, taking about 70 hours to cross 1800 miles of the Turkish countryside. Flying into Khomeini airport doesn't hold any appeal because it robs an epic trip like this of a sense of adventure. The train trip itself in first class is a hair under 40 Euros, which seems suspiciously inexpensive.
Getting a visa as a US citizen is a bit more difficult. You're required to have a tour guide, and an official tourism invite letter, which puts the cost at around $150. Having an official tour guide can either be helpful or quite a hassle. Outside of day trips, I've only had one tour guide and it was a mixed experience.