If a Lebanese or Syrian border official asks if you've ever been to Israel, the correct response is, “Where? Israel doesn't exist, does it?” The country didn't appear on any map I saw in Syria.

But when my partner, Ben, and I were asked the question when leaving Lebanon, I just answered no. The Lebanese officials thought they were onto something. They searched Ben's passport for 15 minutes, looking for a stamp. It occurred to us later that the name Benjamin, which is from the Old Testament, might have raised suspicions.

We were on the trip of a lifetime through 13 countries. Since we're both writers, the journey was as much about sharpening our skills as it was about tourism. But that didn't always complement our need to get across borders.

I was especially nervous about crossing into Jordan from Syria. In a March 2008 article in the Columbia Journalism Review, Jordan was described as having one of the worst records in the Middle East for press freedom. I'd heard that people travelling on tourist visas who were suspected of being journalists had been denied entry. The contents of one of the bags I was carrying were a dead giveaway: laptop, audio recorder, digital SLR camera. When I opened the bag at one point in Lebanon, a local told me I should go to the south, where a missile had just been fired at Israel.

So Ben and I renamed the files on our computers to make them look like travel diaries. We erased the interviews from my recorder and buried a backup folder deep within my computer files. Using a sock, I hid the device I used to split a telephone line in order to record an interview. And we crossed our fingers.

At most border crossings in the Middle East, there are at least two checkpoints to pass through—one for the country you're leaving and one for the country you're entering, with a no man's land in between.

Leaving Syria was easy. Our taxi driver, who spoke as little English as we spoke Arabic, helped us through. After we left the Syrian immigration building, he asked for our passports. We hopped back into the taxi for the five-minute drive to the Jordanian border, but before we got there the taxi driver pulled over. “Cigarettes!” he said, gesturing toward the duty-free shop. We shrugged, not understanding what he was getting at.

Then it occurred to us that he was probably planning to use our passports to buy more than the one carton of cigarettes he was allowed. That seemed okay, since it wouldn't mean breaking any laws. So we expected him to emerge with a few cartons of cigarettes.

But when he came back, he had a plastic bag full of cigarette cartons—way more than we had expected. He tore into one of the cartons and began stashing packs of cigarettes behind the spare tire, under the back seat, and so on.

He gestured for us to take one carton each. We politely declined. He gestured forcefully, motioning us to put one carton in each of our bags. Again we shook our heads.

Maybe I'm just paranoid, but I was imagining those scenes in movies where innocent travellers get tricked by a local into smuggling drugs and end up in a horrible foreign jail. Maybe the taxi driver was in on a scheme and we were being set up to get caught by border officials we would have to bribe, and the driver would get a cut. In any case, there was no way I was going to put those cigarettes in my bag.

When the driver realized it wasn't going to happen, he continued sticking packs in random places in the car and on his person. He put two packs in the glove compartment.

Imagine my anxiety—now we were rolling up to the Jordanian border with my journalist bag, two laptops, and smuggled cigarettes.

We ended up in a lineup of cars that were getting searched. The taxi driver stopped over an open pit from which a border guard could search the underside of the car. We took our bags out while he looked in the trunk and under the hood.

We could see a guard searching the cars in front of us thoroughly, looking under the back seat and searching the glove compartment. A tourist who was ahead of us was having her bags picked over. By this point, I was shaking.

When it was our turn, Ben and I stood respectfully by our bags. The taxi driver spoke to the guard before he started searching the car. He tapped on the sides, checking for things hidden in the doors. I held my breath as he looked through the trunk, lifting up the mat to expose the compartment beneath. But he didn't remove the spare tire, as he had with the cars in front of us. He then moved to the back seat, looking in all of the pockets. But he didn't check under the back seat, as I had seen him do with others.

All he had to do now was get through the front seats and we were clear. He moved through, missing all of the cigarette hiding places—until the glove compartment. Then, quick as lightning, he opened the glove compartment and stuck the two packs of cigarettes into his pocket without a word to our driver.

Then he took our passports. In a serious voice, he asked, “Where are you from?” “Canada,” I squeaked. Then, with a broad smile, he said, “Welcome to Jordan!” We were clear.