To cross a border by land is a part of everyone's round-the-world trip. It should generally be no problem and no hassle to do so wherever that it. However, it can also be funny or bloody hard depending on the countries and circumstances you are in then.
The below are five of my funniest or hardest border-crossing experiences:

1) From Thailand to Cambodia
When: June 2004
Difficulty: Relatively Hard
Comment: This journey back in 2004 has definitely become the funniest tale to tell now, although nobody was laughing or smiling at that time. It was the beginning of my very first round-the-world trip, so I was super keen and excited about everything, and yeah, I was young(er) and a bit careless too.

Here for the first time on the Internet I'm writing down my maiden border-crossing by land:

Things were all going well until I left Bangkok. A nightmare slowly began when I reached the border between Thailand and Cambodia. There were about 30 backpackers trying to get through this border for Siem Reap, Cambodia. Most of us had arranged this trip at those same-same-but-different travel agents on Khaosan Rd. in Bangkok, and all of us must have been told about the same thing upon paying for this trip at the agents: A VIP-bus was going to show up and it would take us all the way to Siem Reap within 4 hours or so.
The fact was that we were first made to wait and wait for our visas to be issued. Waiting so long under the blazing sun with very little shade around, our passports finally came back to us with Cambodian visas but no VIP-bus in sight. After waiting for a couple more hours, two super rusty Nissan pick-up trucks came out of nowhere. They were the only vehicles at the border and seemingly capable of carrying us as passengers. By this time it was already too late to realize that those travel agents in Bangkok were scammers....
Everybody was pissed off at it, but we had no other choice. 30 of us were divided into two groups, and my group decided to have 6 people inside the nearly write-off truck while 10 people including myself were going to be sitting on the back (the loading platform). I initially had a glimpse of hope that 'Yeah, this ride was gonna be so much fun!' But what we still didn't know was how harsh and bumpy the roads in Cambodia were.
On our way to Siem Reap, there were a couple of broken bridges. Hence we had to detour. We also had a serious downpour late in the afternoon and our truck had no roof on the back, so we had to cover ourselves with a big tarp while we were tirelessly hanging on to the back of the truck going through the unpaved muddy road. Furthermore, our truck got a flat tyre in the evening, and when we replaced it with a spare one, the battery ran out, so we had to kick-start the truck by many of us pushing the back of the car in pitch-black. Huh....
I am not joking at all. All these incidents did happen to us in less than half a day in the middle of nowhere in Cambodia. But the worst of all wasn't any of them. It was a young selfish French couple who went on with us all the way, and they kept complaining all the time. They became unbelievably annoying to all of us at some point, we even thought about abandoning them in the landmine-infested bushland during our toilet break! Or else one of us might have shot them dead there. No kidding!

When we finally arrived in Siem Reap, it was past midnight. I was almost brain-dead for the next couple of days. This was all the sketchy travel agent in Khaosan Rd. to blame as well as the French couple. Nevertheless, Angkor temples were magnificent and it was worth such a turbulent border-crossing in the end.
201602 Esky Cambodia 01 Border-crossing

201602 Esky Cambodia 02 Border-crossing

201602 Esky Cambodia 03 Border-crossing

2) From Syria to Jordan
When: September 2010
Difficulty: Relatively Easy (Back then!)
Comment: Not a slightest sense of danger in Syria back then. It was completely safe travelling in now a civil-war-torn country. And not a slightest sense of what was going to happen during our border-crossing from Damascus to Amman either.
Yes. Sometimes it's better and easier (and safer?) not to know everything, which is more or less what happened to us then. More details are described here - 'Taking Part of XXXX'.

3) From Brazil to Paraguay
When: December 2010
Difficulty: Potentially Dangerous
Comment: This was by far the luckiest escape of all due to the most probable consequence of the incident. It was an overnight bus bound for Asunción, Paraguay. I didn't actually see any suspects, and no others on the bus probably saw anybody or anything except our driver (I guess.) Still, seeing the broken windows and their shards scatter everywhere inside the bus was evident enough to give us the shivers after all. More details are described here - 'Night-ride to Asunción'.

4) From Chile to Bolivia
When: February 2011
Difficulty: Bloody Hard because of ....
Comment: The saying - "Ignorance is bliss." - didn't apply to me at all. This is the only border-crossing that I seriously wanted to turn around and head back. It was my tight schedule to blame, or it might have been because of my body; too fit and lacking in extra body fat.
I now think back to the days prior to my illness occurred in the middle of the Andes and it was all meant to happen: Spending a few days on cold-water surfing in Pichilemu (0 meter elevation), two days back in Santiago to cruise around (about 500 meters elevation), one full day inside the bus moving from Santiago to San Pedro de Atacama along the Chilean coast (max 600 meters elevation) and only one day in San Pedro de Atacama (about 2,400 meters elevation). Very unwisely, on the following day I reached 4,300 meters in elevation. Yes, at that time I neither knew that I was supposed to acclimatize myself beforehand nor the word "acclimatization" itself. Hahaha.
My whole body was shaking on the night at 4,300m because it was deadly freezing no matter how many layers I put on or how many blankets I had over myself. Plus, extreme dehydration combined with a sever migraine causing insomnia for me: I really thought that I was going to die soon, so that I begged my driver to take me back down to San Pedro de Atacama. It was that bad!
Very fortunately, the hardest part was this Day 1, and the elevation on the Day 2 went a little bit down to 3,700 meters which was still high for this surfie vagabond, but I was gradually feeling better as my migraine was slowly fading out.
The Day 3 became absolutely worthwhile enduing an ordeal for the past two days. Salar de Uyuni was stunningly beautiful as she was perfectly mirroring her sheer beauty with the azure-coloured sky; Little did I know that some water had filled in the forever dry salt lake with rain-fall on the night before. It was nature's finest magic show. Moreover, Uyuni was an oasis for me in one of the only two landlocked countries in South America where I could step into the water with my own feet, and it was as if resuscitating a nearly mummified lone cactus found in a desert; My body was no longer dehydrated and my acute altitude sickness was completely gone by Uyuni's spell.

In the end I experienced the best and the worst within three days. Hence I've aptly named this experience as "Bolivia's Magic." More details of Uyuni's finest magic show are described here with many photos.
201602 Esky Uyuni 01 Border-crossing

201602 Esky Uyuni 02 Border-crossing

201602 Esky Uyuni 03 Border-crossing

5) A little "border-crossing" in Taiwan
When: January 2013
Difficulty: Easy
Comment: The photo below tells you all. Yes! I crossed a "border" just a little bit and this whole scene was captured so timely by Taiwan's notorious eyes-everywhere-camera.
I was on a little surf-trip with three of my friends then and clearly had no idea of crossing it. A letter was sent to me later and I had to pay the fine (about USD30). This photo is somewhat cute, no?
201602 Esky Taiwan Border-crossing


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