Escaping Iran

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Escaping Iran

Biking to Japan - Week 19

Jun 18, 2025

“I can no longer protect you. If we’re stopped by police for questioning, I should just wave goodbye and leave, because you’ll be on your own.”

Reza’s words echoed in my mind as we dumped our bags into the Peugeot Pars.

Iran was already a Level 4 Do Not Travel country before the missiles and bombs. Now, I reckon the State Department would bump it to Level 5 if that existed.

We were hunkered down about 80 miles north of Tehran, halfway between the capital and the Caspian Sea. Up in the mountains, off a dirt track far from the main road. I thought it was safe, until early Sunday morning, when I heard a bomb go off a few miles to the south. Reza and I both agreed that inaction at this point would be suicide.

The plan was to get out: Afghanistan, Azerbaijan, Armenia, Turkey, or Iraq. Reza leaned toward Afghanistan because it would keep me on track to reach Japan. While I prefered Azerbaijan because it seemed more logistically doable.

So we headed north. We agreed to decide in the car, right before the highway split, giving ourselves time to absorb any last-minute intel.

We chose Azerbaijan.

Reza told me we should speak Spanish together, and that I should say I’m from Spain, if it came to that. But mostly, don’t talk to anyone. A human rights lawyer had warned: “There are simple-minded people here who could kill you.” I had no issue with staying quiet.

The drive took eight hours. We passed maybe a dozen checkpoints, but only got stopped twice. Once, the police wanted to search the car. Reza, with his uncanny charm, talked us out of it. The second time, we were pulled over for speeding. I didn’t say a word at either stop.

The crossing itself was the most intense part of the day.

Azerbaijan had recently opened its land border to Russians, and there was a horde of them 150 deep. A few scattered Europeans. At the Iranian exit, I had a 15-minute interview with a passport officer. He smiled, but it was all business. He asked the same questions over and over, coming at them from different angles to check for consistency. A polite interrogation. Eventually, he waved me through.

Next step: cross the bridge into Azerbaijan.

But instead, I was pulled aside—along with a few Portuguese nationals—for another round of interviews. This time by either the IRGC or the army, I’m not sure. We were led to what looked like a makeshift army bunkhouse. They’d set up an eye scanner in the shower, and a folding table with a desktop computer in the storage closet. Totally unofficial. Like an interrogation room in a war movie.

At that point, I figured it was 50/50 I’d be detained—either for more questioning or as a bargaining chip. One woman broke down crying. She was terrified.

In the end, my “interview” was two questions. It lasted under a minute.

I stepped back into the night, half-expecting someone to call me back. But no one did. I retrieved my bike and pushed it across the bridge into Azerbaijan.

What struck me most wasn’t the danger, it was the sheer chaos. Uniformed men doing everything and nothing all at once. Some were smiling, some laughing. Others shouting, others stern-faced. We would be shuffled into place by one official, then shuffled somewhere else entirely a few minutes later by another. Only to have them all lose interest and wander off in different directions. Total confusion.

Azerbaijan was smoother. Not smooth. But smoother.

Land borders have been closed since COVID. They only opened for us because of the emergency. I needed special authorization, arranged by the U.S. Embassy in Baku. And a normal tourist e-visa, arranged by my friend Matt back in S.F. Thank you, Matt.

I’m writing to you now from Azerbaijan. A country I hadn’t even planned to visit. I don’t know the currency, the culture, the food, the rules. The hotel I went to at 1 am the first night I paid 50AZM—and didn’t know if it was $5 or $50—and still don’t care.

I don’t know where I’m going next. Or what this means to reach Japan.

But I’m still moving.

And I owe that to Reza, who could’ve left at any time to be with his family. I wouldn’t have blamed him.

There’s truly no one else I’d rather have beside me in a moment like that.

Thank you, my friend, stay safe.