Estimated reading time: 11 minutes
Have you read Self-Administered Travel Therapy yet? That might be a helpful starting point. Then, come back to this post.
It was 2017 and I had just gone through a breakup. I was devastated and to top it all off, I had no clients and was making no money. I moved into my parent’s basement until I could figure out my next move; it was humiliating. I had been successful in the past, why was I now struggling? I didn’t know what to do. I’ll just keep writing travel articles for magazines, I thought. No, that’s not enough. I’ll find a PR client. But I don’t want a PR client. Maybe I need to go to school? But all I have is a GED, that’ll take forever to get into a decent school. What will I even study? Nothing in life seemed to be working out. It didn’t dawn on me that maybe I just needed to give myself some time to recover from a bad breakup.
I met my friend for breakfast in Manhattan and we sat at a diner staring at the insurmountable-seeming prices on the menu. I need to be a millionaire just to eat breakfast, I thought. How the hell am I going to make it work in this city? Everything was so much cheaper in California. I could just move to Colorado or somewhere cheaper and make it work there…
“I might move to another state,” I told my friend Tyler.
“I want to move to another country,” he replied.
“Maybe I should take a trip to Spain,” I said. Wait. “You know what? I’m buying a trip right now.” So, I went to Kayak.com and stared at the NYC to Madrid/ Barcelona back to NYC tickets for a few minutes. My credit card information wasn’t saved in the system, so I didn’t have the luxury of making an impulse buy. I took out my credit card and put all the numbers in and got to the confirmation screen—the screen where all it took was one more button to process the transaction. Fuck it. I pressed the button and there it was: a ticket to Spain, ready to go. I did nothing else that day but something felt different: I was free for a moment. I finally did it. I had been wanting to visit Europe and had never pulled the trigger, but now I was doing it.
The trip was going to be eight days long and two days of travel. It was a cheap enough ticket so that it didn’t set me back too much, but more than anything, something changed as soon as that confirmation email hit my inbox. I had done something in the right direction. Eight days isn’t a lot of time, and four or five hundred bucks isn’t a ton of money. Understandably there was to be more expenses I’d have to cover to make this trip, but I didn’t think about it on that day. All I knew was that I was going, and what happened during those eight days I was there in Spain was quite epic…
I landed in Madrid and in lousy Spanish found my way through the airport. I had booked a couple nights at some high-rated hostel and looked up how to get there via public transportation from the airport before getting on the plane. I memorized the stations I needed to transfer at to get to the stop that I could walk to the hostel from since I had no international data plan. I made a few mistakes and looked a little stupid at a few instances when I was trying to communicate but couldn’t really get my point across, but eventually I made it to where I wanted to go and came above ground at my stop.
I looked around and it was everything I had seen in movies. The cafes were everywhere. The busboys were clearing the tables. It was somewhere close to eleven at night. I asked one of the busboys how to get to the street I was looking for. I didn’t have data, so I showed him a screenshot of the Google Maps image that I had taken before takeoff in New York. I had a hard time explaining to him that it wasn’t actually Google Maps, that it was just a photo of Google Maps as he kept swiping his fingers over the screen to zoom in on where I was trying to go.
“No, es un foto,” I kept trying to explain. The roads were all so tiny that I couldn’t even find the street signs, which is why I really needed some help. Finally, he pointed somewhere, and I walked past a few dudes selling weed on the street before finally finding my way to the hostel.
I walked in and talked to the Italian guy working the front desk. We spoke for an hour about Spain and Italy and I told him about my Guinness World Record road trip—as I do too often. Right, I have the Guinness World Record for Longest Journey by Car in a Single Country… but more on that later. The next day I wandered around the city and took photos. Two girls walked in my room later that evening with mate gourds and bombillas—a signature Argentinian drink. I asked if they were from Argentina and one of them looked at me like a damn moron and said, “Uruguay,” then they went to bed. I woke up and walked around the hostel during breakfast and met a French dude that tried to convince me to fly to Ibiza with him as I listened to him future-trip all the many stories of debauchery he expected were to come. I told him I’d think about it and left for a bookstore in downtown Madrid.
On my way there a couple street performers grabbed my phone and took pictures with me without my consent. There were some good photos and I thanked them and carried on. They flipped me off without flipping me off when I didn’t give them a tip. I walked into a casino and bet a couple euros and doubled my money, so I walked back and gave the asshole street performers some money and they smiled. That night I spent the evening dining alone and practicing my Spanish and got back to the hostel and hung out with a bunch of travelers to a late hour of night.
On the third day I had booked a ticket to go to an old town called Toledo the following morning, so it was my last day in Madrid. The two girls from Uruguay that were in my room were planning their day in the common area when I woke up, so I started conversation and asked if they wanted to get dinner later. They said yes. Then I met a girl from Florida and asked her if she wanted to get coffee before dinner. She also said yes, but as we were walking out to the café hours later, the two girls from Uruguay walked by us a bit confused.
“Are we not still going to get dinner?” One of them asked me in Spanish.
“No, no, yes, we are!” I said, but I didn’t know how to explain that me and this other chick were just going to grab a cup of coffee, so I just invited them to come with us fearing I might’ve messed up the opportunity. We all went out and had a good time then walked around the plaza. Later that night we all stayed up and joked around in the kitchen. The girl from Florida started chatting with some Dutch guy. I stayed up till four talking to one of the girls from Uruguay—the one that stared me down when I asked if she was from Argentina. Finally, after many hours of broken Spanish conversation with her, I said, “Okay, I gotta go to bed.” We had exchanged numbers on WhatsApp and I gave her a kiss on the lips and when I got to my room she sent me a message that translated to something along the lines of “why didn’t you do more than kiss me?” I told her to meet me in the hallway and we made out like kids. It was fun. Then we stole some blankets from the laundry room and went to the bathroom and had sex.
The next day I took a train to the bus that took me to Toledo and when I got off at the station there was nothing but cobblestone roads and hills. I walked up some hill with my bag and got to this bohemian-looking hostel and walked into my room that I had booked a day before and there was a guy from London that looked just like me, but taller. I told him I met a wonderful girl from South America, and he told me about all the people he met on his trip. It was a small hostel but packed to the brim with travelers, so by evening, after all of us met, we decided to go out for dinner together that night.
It was about ten of us and we dined all night then hiked up some mountain to see the city lights from above then went to some odd club that was in a medieval-looking church. It was a massive interior and we were the only ones there; a giant feeling of emptiness. I was flirting with a girl from San Francisco, but it appeared she was more into my friend, so I went back to the hostel. I woke up and my buddy wasn’t there. I assumed they had just fucked somewhere, and all was fine, but when I found him outside the hostel smoking a cigarette, he said with a stressed look on his face, “Man, I think I fucked up.”
Turned out the girl had gotten quite sick after the club because on their way back to the hostel they drunkenly broke into a bar and drank all their booze. “I think it was on surveillance mate,” he told me. “We gotta get out of here.”
He had his car parked down the street since he was road-tripping Europe and said, “Let’s go to Madrid.” So, even though I was just there, I hopped in his car anyway. He had a surfboard strapped to the top of the car that needed constant attention, but that’s just a detail. Point is, we drove a couple hours back to Madrid and went to some weird theatrical zombie dance club later that night that can only be described as Rocky Horror Picture show meets the Jersey Shore, then a day after that he said, “Let’s drive to Barcelona.” So, we took another road trip—about seven hours—to Barcelona.
It was during the Catalonian protests, so the city was mad with patriotism and Catalonian flags. My friend and I were a team by the time we arrived at the hostel, so when we found out they had a rooftop bar, we went up right away. We met a bunch of flight attendants in the elevator and asked if we could join them to scour the town, then we went to a bar and my friend met a girl, as did I. We had fun then went to bed.
The next day we looked at all the Gaudi architecture, and along our walk, passed another traveler that my buddy had met a few countries back. They made plans to meet up later on and I came with him. There was a big protest on the beach about the separation from the rest of Spain and there were all these support concerts celebrating the movement that we took part in as we roamed around through the crowd and explored the culture. Eventually, my friend again disappeared with that girl and I walked around with the girl’s friend she had come with until we realized that we didn’t like each other. So, I went to the metro, but the trains were closed from the chaos. I had to figure out a way to get to my hostel, which was like thirty minutes from the beach of Barcelona. When I finally got back, I rolled a cigarette and smoked outside on a quaint narrow road at about three in the morning and met some dude from Buenos Aires. We talked for a bit before I went to bed. The next day my buddy from London left for some other country and I stayed in Barcelona.
I had to write an article to make some money, so I went to the quieter part of the hostel to write and there was a girl crying. “Are you okay?” I asked her.
“No,” she cried.
Turns out she was working in England but had just gotten deported from breaking some sort of rule and would now have to go back to her home country of Chile. I asked if there was some way that we could make the day fun for her, and she said she wanted to go to the beach, so we went to the Ferris wheel then to the beach then got some food then I asked if she wanted to get a private room with me at the hostel. She said yes but there were none available that night, so we went to the basement and snuck into this massage room and began to have sex, but people kept walking in on us. That was uncomfortable. We decided to just go up to her room, where there were ten other people staying, and put a towel around her bed and had sex in front of everyone. What a wild experience that was.
The next day I was scheduled to fly back to New York, so the Chilean girl took the train with me all the way to the airport and saw me off. It was an insane fucking time. I couldn’t believe how much had gotten done. The point of all this is to say that I spent no more than $800 on that entire trip—including airfare—and did it all in under two weeks. That was only one trip of many. It doesn’t take much time or money to begin your vagabonding career as long as you follow a few principles no matter where you are.
Here’s Secret #1: HOW TO QUICKLY LEAP TO YOUR FIRST ADVENTURE
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