Background: Since 2007, I have been taking bus trips along the Pan-American Highway. I have done 12,000 miles of it so far, which is approximately 88% of the road that stretches from the Arctic Ocean to the tip of South America. I have two segments left. This summer, I will travel by van along the Dalton Highway from Fairbanks to Prudhoe Bay, Alaska. Next year, I will finish with a bus trip from Lima, Peru, through Ecuador, to the frontier town of Turbo, Colombia (along the edge of the Darien Gap).

While I prepare for my Alaska trip, I thought I would share with you my experiences at the border crossings. Oftentimes, the border crossing is the most exciting, and dangerous, part of the journey. It certainly gives you insight about each country’s culture, governance, and character. 

I will rank the border crossings I used, from least to most “challenging”.

13. Canada (Yukon) to U.S. (Alaska): This crossing was by far the easiest, quickest, and safest. It is hard to imagine anything nefarious taking place at this remote border crossing. When our van pulled up, there was just one friendly, and probably bored, U.S. Border Patrol agent. Our van ferried people and freight between Whitehorse and Fairbanks regularly, so it had both Yukon and Alaska plates. On our trip, the van was carrying the driver, his daughter, me, and two cases of soda. We were waved through. I didn’t even have to step out of the van. What a breeze!

12. Chile to Argentina (Lake District): Despite the long-ish wait, the scenery was spectacular. It reminded me of the Swiss Alps between Geneva and Zermatt. Plus, there were some long-distance motorcycles to admire.

Interesting trivia: Chilean cops are called carabineros. Argentinean cops are called gendarmeries.

10 (Tied). Argentina to Chile to Argentina (Tierra del Fuego): Down at the bottom of civilization, you have to briefly enter Chile to get to Argentine Tierra del Fuego. The Chilean side is always quicker and more efficient than the Argentine side. With Argentina, there is always more drama and pomp, even for the most mundane of bureaucratic acts. A big portrait of La Presidenta, with sash, is in every government building. I really got a kick out of the signage that declared a part of Antarctica as Argentine territory.

9. Peru to Chile: By far, Chile has the most professional law enforcement in Latin America. A search of my backpack revealed a big package of beef jerky. The guards didn’t know what it was, so I had to pantomime “dried cow”. It worked, I think, and they let me through.

8. El Salvador to Honduras: It says something about a country when you can enter incognito and the country doesn’t even care. To me, it means no one wants to go there. It also means that even if somebody does, there is nothing the migrant can do to make the country any worse.

That was the case with Honduras. It was the only country where I didn’t have to hand my passport to a border agent. Rather, one of our bus’s stewards just collected everyone’s passports, and, 30 minutes later, returned everyone’s passports, with fresh stamps. We didn’t even have to step off the bus. Truth be told, no one wanted to step off the bus. I snuck a photo of the border crossing from the bus (see photo immediately above). Unfortunately, those two dudes hanging out by/on a burned out Taurus perfectly summed up Honduras.

7. Nicaragua to Costa Rica: I have never been to the former Soviet Union, but I’m sure this little corner of the Western Hemisphere is just like it. Crumbling concrete was everywhere. Lead paint chips littered the ground. It looked like the crossing was once a grandiose and gleaming public works project. But decades of neglect just made it sad.

I spent hours loitering the parking lot. This Ford RV with Kentucky plates caught my attention. A young hippy family with a litter of kids was found inside.

6. Honduras to Nicaragua: The first thing you notice is that Daniel Ortega is in charge. His party’s campaign posters, and his face, are plastered everywhere. You immediately get the sense that Nicaragua is a democracy in name only. 

The line to get through customs was slow. A pack of poor boys, and a teenaged girl, were simultaneously begging, offering to carry our luggage, and selling snacks and drinks. One boy, with puppy dog eyes, knew that his cuteness alone was good enough to extract a dollar or two from sappy hearted norteamericanos. He tugged at my arm and pleaded “Mira”. I looked down and he shot me a sad look. It didn’t work on me.

5. Costa Rica to Panama: Not the most challenging, but certainly the most interesting. Our bus arrived at the border crossing before sunrise so that we would be the first ones processed when the border opened in the morning. Being a Type A personality when it comes to travel, I bolted to the front of the line with my backpack and waited. And waited. In the dark. There were just enough shady characters milling about that I didn’t feel comfortable leaving the safety of my fellow passengers and looking for the loo. After a couple of hours of standing with a full bladder, exhausted, and dirty, I was miserable. Then, I turned around and looked up (see photo immediately above). It was the most beautiful sunrise I had ever seen. And all was well.

The Costa Rican side finally opened. After getting an exit stamp, I walked 100 yards to the Panama side. And waited some more. Stray dogs were everywhere, and one took a long nap under our bus. Then, the experience took a turn for the bizarre. A little middle aged lady in uniform corralled all of the passengers from my bus into a large circular room. We were lined up along the wall, with our luggage in front of us on tables. Then, just before our belongings were thoroughly examined, the official asked us to bow our heads, hold hands, and say a prayer.

4. U.S. to Canada (Vancouver): This benign crossing was challenging because of the polite but firm questioning by Canadian authorities. I had been riding Greyhound since I got on in Oakland about 24 hours earlier. I was tired, disheveled, and malodorous. The bus let everyone get off on the American side. We had to walk through a building connecting the border, and got picked up by the bus on the Canada side.

I get up to the Canadian border agent. He riffles through my passport.

Q: Where are you going?

A: Alaska.

Q: Where are you coming from?

A: California.

Q: Why didn’t you just fly?

A: Because I want to get there by bus and van.

Q: Where are you staying in Alaska?

A: I don’t know. As soon as I get to Alaska, I’m flying back home.

Q: What do you do for a living?

A: I’m a lawyer.

Q: Follow me.

Apparently, my answers did not pass the sniff test. It took several more minutes of questioning, and me showing the agent my bio (and picture) on my firm’s website, for him to be convinced that I was kosher. 

3. U.S. (San Ysidro) to Mexico (Tijuana): Who knew there was going to be drama traveling to Mexico from America? After being dropped off by the San Diego trolley, I walked across the border to TJ. This was at the height of narco-murders. The news at the time was that the area had run out of coffins. There were no gringos to be seen, anywhere. There were no officials or border posts on the Mexican side, so I hopped in a cab and went to the Tijuana bus station.

With a bus ticket to Mexico City in hand, I hung out in the station lobby. As a tall-ish Asian guy, I stuck out like a sore thumb. A tiny but rotund Federale came up to me and asked for my passport. I acquiesced. He barked at me in Spanish: Where is your entry stamp? Shit, I thought, where was I supposed to get a stamp? He ordered me to follow him to his office.

I wasn’t expecting legal trouble, but I was expecting a shakedown. He takes me into his office. It’s me, him, and his very young and very female assistant. The office is so tiny, when I turn, my backpack scrapes against the wall. Surprisingly, they just stamp my passport, tell me to be safe, and let me go. Whew.

2. Guatemala to El Salvador: Central American border crossings are notoriously hectic and sketchy. They are even more so at night. I did everything I could to make sure I did not reach this border at night. I failed. What concerned me was that the only lighting was from inside the border post. There was no lighting in the parking lot. There was no lighting immediately outside the border post. It was pitch dark. You could literally be stabbed, robbed, and left for dead 10 feet from the post’s door and no one would notice, or care.

Once I got in the building, I was in a long, serpentine line. The ratio of travelers to pushy money changers was 1:1. I made it through. As I got back in the bus on the Salvadorean side, I looked back at the border. It was still pitch dark, except for headlights from random trucks. The imaginary line was so porous, northbound trucks carrying tons of contraband and dozens of migrants heading to el norte on foot could be right in front of me, and I wouldn’t even know.

1. Mexico to Guatemala: One of the reasons this crossing was the most challenging, and overwhelming, is because this was my first Third World border crossing. A bridge separated the two countries. I had to go to the Mexican side first to get an exit stamp. For some reason, I ended up being the last person from our bus in line. When I got to the Mexican official, he was saying something in Spanish that I simply could not decipher. Finally, he mentioned an amount, in pesos. I had already exchanged all of my pesos for quetzales an hour earlier. Fortunately, he accepted US currency– $20. I didn’t want to argue because I didn’t want the bus to leave without me. To this day, I am uncertain whether this fee was legitimate.

Crossing the bridge on foot was nerve wracking. I wore my backpack on my chest and clutched it with all my strength. There were hundreds of locals, loitering, and they were all male. Everyone 12 years of age and under came up to either beg for money or offer to carry my bag. Everyone older than 12 offered to exchange money or just stared at me from a distance, like vultures salivating over carrion. I escaped unscathed, but I will always remember the menacing experience.

Images source: Hooniverse/Jim Yu, Copyright 2014