I spent a lot of my first trip around the world partying. I was twenty-five and ready to break free after a quarter-century of living a very dependent, middle-class life. In my mind, backpacking was a lot about meeting fellow travelers, partying and saying yes to anything that came your way. And that often leads to some humiliating experiences.

Like entering a boxing ring in Ko Phi Phi, Thailand.

Before I started that trip in 2006, I used the MySpace website to meet travelers in advance, because, as an introvert, I was very worried that I wouldn’t make any friends on the road. There were tons of travel groups on MySpace, so I reached out to people hoping to meet up with them on a trip. (I started using the web as a social tool: I had a blog in 2001, and I met my first girlfriend on Friendster when meeting people online was taboo.)

After landing in Bangkok later that year, I ran into Lindsay at the airport, the Brit I was supposed to meet in Krabi later that week. She was with her friends John and Stephanie. As luck would have it, we were on the same flight to Phuket, so we decided to start our trip early.

In Phuket, we booked a stay at the hostel made famous by the movie the beach. It was as terrible as the movie, with thin walls, dirty bathrooms and hard beds. We stayed one night.

From there, we went to Ko Phi Phi, where we planned to spend three nights. The island was still reeling from the tsunami that devastated it two years ago, with noise as it tried to rebuild itself. There was debris and construction everywhere, and many businesses were still closed and homes abandoned.

We found a cheap room at the far end of the main town, bunking together to save money, a tourist’s most precious commodity.

That night, we did what backpackers do on the island: we partied. We ate cheap food at a bustling night market, with vendors selling overpriced Pad Thai to passers-by who didn’t know any better. From there, slowly get drunk before ending up in a reggae bar, famous for two reasons: buckets of cheap booze and a boxing ring in the middle.

But the ring is not for watching professional Thai boxers. No, it’s there so backpackers can watch other backpackers beat each other up for free buckets of booze. (A “bucket” is Thai whiskey, Red Bull, and Coke in a kid’s beach pail. It pretty much smashes you.)

As we got drunker and drunker, James dared me to box in the ring. “C’mon! We need more booze,” he said, motioning me forward.

As the night wore on and the alcohol did its work, I decided to call it bullshit. “Well, I will,” I agreed, admitting the urge to say yes to anything and impress my new friends.

I got in the ring with a big German guy who was almost as drunk as me.

“Go easy on me,” I said. “I’ve never been in a fight.”

“Never mind. It’s just for fun anyway,” he replied in a slurred, accented voice.

Being drunk, I got a little overzealous and wasn’t “easy” on it. I became aggressive, landed blows where I could and the first round was called in my favour.

In the second, not wanting to lose to an American half his size, he fought back. Even in my drunken state, his blows hurt.

That round was called for.

Both of us were a bit aggressive in the final round. He beat me easily, as the ref, not wanting to get pummeled too much, quickly called the round — and the match — for him.

But everyone loves an underdog, so boos erupted from the audience.

In an effort to please the crowd, the bar also gave me free buckets, and the German guy and I cheered each other on. His friends joined me, and we partied the night away.

The next morning, when I woke up, I was stiff as a board and had a terrible hangover. Although slightly bruised, I could barely move. Every part of my body hurts.

“Why is everything sad? What did we do last night?”

It took a few minutes, and then it hit me (so to speak).

“Oh, yeah, I boxed someone last night!”

While I hadn’t thought about the effects on my body the night before, I was now well connected to them. I felt the truck back up and down my body several times as I lay in bed.

My friends and I laughed and joked about how stupid it was for someone twice my size to box for alcohol. I was grieving until my friends got ready, until finally I had to get dressed myself. We headed to the beach to soak up the sun on the sand and have some breakfast.

Boxing in that ring was one of the most spontaneous things I did on that trip and, while I’ll never do it again, it’s one of those “fuck yeah” moments that brought me closer to my friends and made a great memory. .

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Book Your Trip: Logistical Tips and Tricks

Book your flight
Find cheap flights using Skyscanner. It’s my favorite search engine because it finds websites and airlines from all over the world so you always know that no stone is left unturned.

Book your accommodation
You can book your hostel Hostelworld. Use if you want to stay somewhere other than a hostel Booking.com Because it consistently offers the cheapest rates for guesthouses and hotels.

Don’t forget travel insurance
Travel insurance will protect you against illness, injury, theft and cancellation. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I have had to use it many times in the past. My favorite companies that provide great service and value are:

Want to travel for free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodations – all at no extra cost. Check out my guide to choosing the right card and my current favorites to get started, and check out the latest great deals.

Need help finding activities for your trip?
Get your guide There is a huge online marketplace where you can find great walking tours, fun excursions, skip-the-line tickets, private guides and more.

Ready to book your trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use while traveling. They are best in class and you can’t go wrong using them on your trip.

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