My first solo trip to Japan was the product of wanderlust and a bottle of white wine at 2 in the morning. It was the year I graduated college, and I had rushed into the corporate world right out of the gate. I was working freelance gigs in New York City, and so there was a bit of flexibility in my schedule.

Enough flexibility even for a month-long trip to Japan.

Did I have enough money saved up? Well, I had at the time what I considered to be a sizable nest egg (about $3,500) and shiny new credit card with no balance (23 year-old Tom didn’t have much in the way of financial literacy).

I was itching to get out of the rat-race I had only just entered, so I did it… I booked a round-trip ticket to Japan… for a month… in January… with no plan. Oh, and don’t let me forget about the 12-hour layover in Beijing. I think it cost me around $600 at the time. That certainly wasn’t a trivial amount of money for me, but I considered it a bargain given that it was teleporting me to the other side of the globe.

I don’t even know why I chose Japan. I was never one of those “anime kids”, and to be honest, I knew little about the culture aside from Sushi.

I think I just wanted a crazy experience. And for better or worse, that’s what I got.

I think I just wanted a crazy experience. And for better or worse, that’s what I got.

The journey there

My dad dropped me off at JFK airport the day of my departure. I think he was more nervous than I was. I had the confidence, dynamism, and naivety of an indestructible twenty-something… unaware of all that could go wrong.

The sheer confidence is something that 33 year-old me envies, especially given the fact that I only had an AirBNB booked for the first week of my month-long trip. I figured I would make the rest up as I went along.

I’ll never forget the feeling of getting on that plane. I was flying Air China and there was some relaxing Chinese instrumental music playing over the speakers. My chest was filled with excitement. Of course, I had gone places by myself before… but this was the first time that I had felt the unbridled freedom of spontaneous adventure.

Some nerves did start to kick once I had found my way to my seat. So I searched my seat-back screen for something to distract me and landed on listening to the latest Luke Bryan album. And to this day, associating “Kill the Lights”, an American country album, with Japan is a fun little inside joke I have with myself.

The man sitting next to me was a middle-aged man from China. At some point during the 12-hour flight to Beijing, we got to talking… well not so much talking as doodling. He didn’t speak any English and I didn’t speak any Chinese, but we drew on a napkin to tell each other about ourselves.

He lived somewhere in Western China and had a wife and a few kids. I drew a map of the US in return, along with stick figures of my family. In retrospect, it was a beautiful moment between two humans… using art to transcend language barriers.

It was a beautiful moment between two humans… using art to transcend language barriers.

We landed in China in the early hours of the evening and I was in for a 12-hour layover for which I had booked no accommodations. But I was a 23 year-old riding the high of adventure… and I was more malleable than I am today.

I found some food, as well as a vending machine that sold Tsingtao beers for a dollar (I probably spent 6 to 8 dollars on beer that evening). I wandered about the airport for a bit, taking in the novelties of the Chinese adverts and subtle differences in amenities, before curling up on a row of seats with my jacket as a blanket.

Little tip, the Beijing airport is quite drafty, and it was right around freezing outside. So if you’re ever considering a 12-hour, overnight layover in Beijing in order to save $100… do yourself a favor and splurge.

The second leg of my trip, from Beijing to Tokyo, was substantially shorter. Though we did have some serious “rollercoaster” turbulence and the guy next to me was sniffling and coughing up a storm. I’m a hypochondriac under normal circumstances, and I’m downright paranoid when at the threshold of a month-long trip.

One element of the in-flight meal was a Century Egg. Look it up. I can count on one hand the culinary items I have not ventured to try… and this was one of them. Mister sniffles scarfed his down and then gestured as to whether he could eat mine… I gladly obliged.

Customs at Tokyo Haneda airport was a breeze. And thanks to some very clear instructions from my AirBNB hosts, I found my way to their neck of the woods via airport shuttle.

They lived in a luxury condo building on Odaiba, an artificial island in Tokyo with shopping centers, a giant Gundam robot, and a replica of the Statue of Liberty. There was more to it than that, but those definitely jump to the top of the spark-notes in my memory.

My hosts greeted me at the door (I was renting a bedroom in their condo). Of course, I made the American mistake of not taking off my shoes. We had a fun little language-barrier moment of that and I was embarrassed. They showed me to my room… a modest space with a futon, a desk, a city-view, and a complimentary bottle of Japanese whiskey.

I used the bathroom (Japanese toilets for the win), slammed some Vitamin C and a shot of whiskey, and then went to bed. I don’t know how long I slept for, or what time I went to bed, but it was well over 12 hours. The drafty Beijing layover had done more of a number on my system than I had thought.

My first week in Japan… before it all went wrong

My first week in Tokyo was amazing… and in retrospect, might have been a perfectly satisfactory trip.

I must have logged tens of thousands of steps that week. The Rainbow Bridge connected Odaiba to the ‘mainland’ and was very much walkable. Though I think I spent my first day exploring the island. It was all new to me, and given that I would be there for a month, I was in no rush.

Odaiba was an interesting spot. Very posh, very new, and like I said, lots of shopping centers. There were peculiar things like the giant Gundam robot (that’s an old anime show for the people who didn’t get bullied in middle school) and the very strange replica of the Statue of Liberty. I explored stores, arcades, and the ins-and-outs of the different complexes there.

Like I said, all new to me– all interesting.

I gathered the gumption early-on to go to nearby restaurant on my own. Well, “alone” was really the only option I had. It was about a block away from my AirBNB and was a semi-casual restaurant/bar setup. I was a bit intimidated, to be sure, but swallowed my nerves and took a seat at the bar.

If you’re looking for a surefire way to kill your social anxiety, go dine alone in a foreign country where you don’t speak the language.

If you’re looking for a surefire way to kill your social anxiety, go dine alone in a foreign country where you don’t speak the language.

Communicating with the bartender was awkward at first… I pointed at random things on a Japanese menu (this was before Google lens), and I think ended up with an Asahi to drink.

There was one other couple at the bar. The man must have seen me struggling with my order and decided to introduce himself. It turned out that he worked for Sony and traveled to San Francisco often. His wife also spoke some English and was very friendly.

They took a liking to me and took it upon themselves to introduce me to a bunch of different Japanese foods and Sakes. What dumb luck I had stumbled into– they paid for everything… countless different dishes and five to six different Sakes.

I remember there was a fried fish dish. The husband pulled the bones out in one sweep with a pair of chop sticks. And there was lots of sashimi… the chef (now cool with me since I had a couple of translators) made a joke about how easy it was to “cook” as he gestured to his knife.

They gave me tasting notes before trying each Sake, explaining which ones were sweeter and which ones were dryer. We took a picture at the end of the night with me holding the bottle of Sake I preferred most, and we’re still friends on Facebook to this day.

That interaction gave me the confidence I needed to start exploring the rest of Tokyo. I ventured across the Rainbow Bridge, and then figured out the train after determining that walking said bridge every day would be unsustainable.

I went on to see so many amazing things that first week… Tokyo Tower, the Chinese Terracotta Army at the Tokyo Museum of Art, some crazy smoke-filled arcades, multi-story porn shops… unfiltered Americans walking around dressed as their favorite anime character. It was all sublime… and all so different from anything I’d experienced before.

This was certainly the adventure and change of scenery that I’d been searching for.

The food was amazing too. I had cold soba noodles with prawn tempura, real-deal ramen, Sushi from one of those conveyor belt places… and yes, American food– from an “American” restaurant. I couldn’t help myself, I had to see what an American restaurant was all about in the context of a foreign country.

But oddly, I was starting to get some sort of “cabin fever”. I was in one of the most densely populated cities in the world and was constantly surrounded by people… but I didn’t speak the language, and few people spoke English. So I was almost going stir-crazy from not conversing with anyone.

So, I opened the Meetup app to see what I could find. I had used it in New York to much success, and sure enough, I found a Tokyo pub crawl aimed at tourists and expats. It was scheduled for the night before I was meant to check out of my AirBNB, so I figured I would go have a few beers, talk to some English speakers, and then be on my way.

What could go wrong?

This is where everything went wrong

I got to the starting point bar early, along with a group of guys from Australia who were in Tokyo for a bachelor party. They invited me to grab some food with them, but “grab some food” really just meant preemptively slamming some beers before the crawl. This was probably my first mistake.

The pub crawl was packed with people from all around the world, and the hosts gave everyone a welcome shot before we started. The promo as a whole was that we would go to a bunch of different clubs and bars and we would get a free shot at each spot. I think I paid like $30 US for my ticket? Crazy 2016 prices.

We got going, walking through the streets of Tokyo, popping into different clubs, and all around having a blast. I was making friends, dancing, and yes… taking those welcome shots at each place (in addition to the ones my newfound friends were giving me).

Now, I don’t know what happened next. The unaccountable Tom likes to believe he was drugged… but the accountable Tom knows that he had way too much alcohol on a semi-empty stomach. The last thing I remember is climbing a flight of stairs to head to the next spot.

And then I blacked out.

I can’t account for 5-6 hours of that night, and I ended that evening with $5,000 worth of credit card debt (that I didn’t remember spending) and my checking account all but drained.

Dang pub crawls.

I arrived back at my AirBNB around 7am, with a 10am check out time. I think I slept for an hour, and then woke in a panic and packed my things in record time. Note that I still had not booked any accommodations for my remaining time in Japan, so at this point, I was ‘houseless’… wandering the streets of Tokyo and hopping from one WiFi hot spot to another to try and find the cheapest possible place to spend a couple of nights and regroup.

I had one checking account with less than $500 in it, and one credit card (which got cancelled when I called to claim fraud). So $500 to my name with three weeks left in one of the most expensive countries in the world.

I ended up finding a cheap hostel on Hostel World and booked it for a couple of nights. It was a pod situation (a bunch of bunks in a shared space with partition curtains). I crawled into my $25 space, cried a bit, and went into hibernation mode. For two days, I stayed put. I hardly ate anything, and for a time, I felt as though I should cocoon myself until it was time to head back to the US.

I was able to move up my return flight by a few days, but I still had over two penniless weeks to reckon with. Eventually, once my shame began to pass, I decided that I had to make something of my remaining time in Japan.

7/11 became my best friend. But it’s true what they say… Japanese 7/11 is on another level. Real food, at a cheap price. For the next couple of weeks, I survived off of Gyoza dumplings, Onigiri, Noodles, and these concrete-like protein bars. My daily calorie intake could not have been more than 500-700 calories. All told, I think I must have lost close to 20 pounds on this trip.

Picking up the pieces

The hostel was a cheap solution, but I found an even cheaper place– an AirBNB about 45 minutes outside of Tokyo. I remember it snowing when I moved to that spot… and trudging through snow in a Tokyo suburb did not make things easier when I was trying to decipher Japanese street signs and my AirBNB host’s screenshots. There was no WiFi and no data, so I was going off of screenshots and gumption.

I finally found the place. The host had set up a hostel-like situation in his guest room– a few sleeping pods with partition curtains… seemed to be a theme. There were a couple of other guys staying there who turned out to be friendly. The host shared some dumplings with us on the first day.

From here, I continued my semi-depressive episode, but compelled myself to commute into Tokyo and see some of the sights that I had missed in my first week. Once the new sights started spiking my dopamine again, my spirits began to lift.

My dad also reached out during this time, wondering why my photo uploads had stopped so suddenly. I gave him the abridged version of my calamity and he ended up lending me an extra $500. My total trip funds for the remaining time were still under $1000, but this at least gave me the confidence that I could see at least one other place before returning home.

I don’t quite remember how this came to be, but one of the other guys in the AirBNB was headed home to Kamakura (a beach town South of Tokyo) and invited me to go with him. Having no plans and limited funds, I gladly accepted. We got on a train the following day.

Kamakura reminded me of a Japanese California– a State which I hadn’t been to yet at this point in my life. But based on the pictures and movies I’d seen, Kamakura very much reminded me of Venice beach… a laid back beach town with narrow-street suburbs and surf/nautical motifs adorning the houses.

We dropped our things at his parents’ house next to a couple of tatami mats and then went out exploring. The Great Buddha, Kamakura’s largest claim to fame, was shrouded in scaffolding (as has been my luck for a number of sites around the world), but I at least got a small glimpse of it.

The rest of the afternoon was spent walking through busy markets and alongside scenic coastal vistas. I ate a bowl of rice with a layer of (I think) raw, tiny fish… eyeballs, scales, and everything. Maybe it was consecutive sub-500 calorie days, but it actually tasted pretty good.

That night, we went out for dinner at a dimly-lit yakitori bar. It was difficult to tell which was filling my lungs with more smoke– the bbq grills or the cigarettes. My newfound friend informed me that he was paying for everything, claiming to have won a large chunk of change playing Pachinko earlier that week. Of course I didn’t question anything, and proceeded to enjoy yet another (free) culinary tour of Japanese food (along with copious amounts of Asahi).

I think I ate chicken testicles. Our communication was pretty strained and I don’t know if chickens even have testicles… but they were, I remember them tasting… different.

Kyoto (on a budget)

A couple days later, I booked a train ticket down to Kyoto. Having successfully killed a few days with my wallowing, and then getting free board, I felt more confident that I had the funds to see at least one more major city before my return flight.

The train, for me, was as much an attraction as the destination. I’d never taken a Japanese bullet train before and was excited to feel what a 200 mph ground speed felt like. I guess unsurprisingly, it didn’t feel like much of anything.

What was surprising were the indoor smoking cabins– little glass-enclosed compartments with men and women smoking their hearts out. I don’t know why; but I guess I thought a country as clean and polished as Japan would have fewer smokers than the US.

Kyoto was beautiful. If Tokyo was electricity, Kyoto was its analog cousin. At this point, I finally felt as though my trip was resuming after the mountainous speed bump. Of course, I was still in a tight spot financially, and as such, was limiting myself to one ‘restaurant’ meal per day, with 7/11 continuing to account for the remainder of my calories.

To tell you the truth, the memories around this part of my trip aren’t quite as vivid as those of the first act… it’s funny how stress really sears itself into your psyche.

It’s funny how stress really sears itself into your psyche.

However, I do remember seeing a ton of amazing things– ancient temples, shinto shrines, beautiful nature, and MONKEYS! The latter were probably my favorite. It was the Arashiyama Monkey Park– dozens of trails leading up a mountain with monkeys scurrying about. They were probably about the size of a large cat… maybe a raccoon.

For my “ugly American” moment (one of many on this trip, to be fair), I looked one of the monkeys in the eyes. There were several signs (in English) advising against this, but of course I needed to touch the stove to learn that it was hot.

The recipient of my gaze began grunting and smacking the ground with its hand (paw?). I got the message and hastily walked in the other direction.

The other two standouts from Kyoto were the Arashiyama Bamboo Forest (as Instagram-worthy in real life as on, well… Instagram!) and the Onsen (natural hot spring).

I forget which Onsen I went to (travel-blogger of the year right here), but I want to say that it was North of Kyoto. However, I could have just equated it with being in the North because it felt colder there.

There was one other person in the train car on the way there… clearly from the US or Canada. We got to speaking and it turned out that he was from the town next to MY hometown in New Jersey! Thousands of miles away and the only other person on this random train car was from where I was from.

It’s experiences like that that make me believe in simulation theory… or maybe I just had a casual brush-in with a possible serial killer. I prefer to believe the former.

The Onsen was a novel experience for me. Nudity around other men wasn’t really (and still isn’t) the locker room norm for my generation in the US. So getting naked and sitting in a hot spring with other men who were also naked was a bit nerve-racking.

But I was alone and on the other side of the world… so what was there to be embarrassed about?

I was alone and on the other side of the world… so what was there to be embarrassed about?

I was required to shower off before getting in, and then I got in and just sat there for thirty minutes or so. Aside from the side glances, it was a really peaceful experience! The air was cold, the water was hot. I closed my eyes and took in the sounds of the Japanese countryside as dusk began to fall.

Like I mentioned before, I was still primarily on my 7/11 diet… but did allow myself a few affordable restaurant outings. By no means was it fine dining, but I did have some good Yakisoba, one of those Japanese omelettes, and I downed a few pints of Asahi alongside a couple of Australian ski instructors.

My last night in Japan

I returned to Tokyo the day before my return flight to the United States. I’d love to say that I ’lived it up’ or that I had one last blowout in Tokyo… but that was not the case. Both financially and emotionally, I was running on fumes.

I booked the cheapest private room I could find and I forget entirely where in Tokyo it was. After checking in, I went to the nearest market and bought a large bag of fun-sized green tea-flavored KitKat bars.

With multiple weeks of ~1,000 calorie days under my (now quite loose) belt, I went back up to the room and spent the night eating the entire bag of KitKat bars and streaming The Big Bang Theory on Netflix (sitcoms have always been visual comfort food for me).

The next day, I made my way back to the airport via public transit and made it through security with less than two US dollars to my name. My return trip was the same as my arrival, but in reverse… thankfully with a comparatively short layover in Beijing this time.

I got back to the US, found a new freelance design gig in New York, and began replenishing my bank account. Of course, the story I recounted to my friends at the time was far more glamorous than the reality… but ten years later, I’m glad I can take a more sober look at this trip and remember it for all that it was, both the good and the bad.

If you’re not an irresponsible dip-shit, I’d say Japan is a fantastic (and very safe) destination for a first solo trip.

What I learned

1. Don’t get rip-roaringly intoxicated on a solo trip… probably won’t end well.
2. Have more than one backup credit card.
3. Have a way to make money while you travel. This was the trip that inspired me to find some remote work and become a digital nomad.
4. If you’re not going to work during that dream trip, you probably need more savings than you think.
5. People are generally friendly.
6. Australians have livers of steel.