Flying Solo: My First Crazy Night in Japan


The view from my 14th floor hotel room in Tokyo.

In April 2015, I took my first ever solo trip to a place that is still part of my top three favorites in the whole entire world: Japan.

I’ve briefly talked about this trip in other blog posts, but I kept telling myself that I would sit down and write a more detailed account later on. Guess that time is now!

First I want to start by saying that Japan was the most meticulously planned trip of any of the ones I’ve been on thus far. By the time I was ready to spend my year in Australia (as you may well know if you’ve read my other posts), my planning consisted of a plane ticket, a hostel for two weeks, and nothing else. So I definitely changed a lot during the year between both trips, and although I made some mistakes this first time around, I’m still proud of what I have accomplished, and I’m grateful for the learning experiences I was able to take from my first time out of the U.S. solo dolo.

So why Japan? Why then?

Ultimately, it was Facebook (again) that led me to the decision to buy a plane ticket to Japan. A co-worker of mine posted about a flash sale that Delta airlines was having during which round-trip flights to Japan were only $600. Originally, I hadn’t planned on doing the trip solo, but I knew that I wanted to go in April because of the cherry blossom season, and the absolute cheapest tickets I could find in April happened to fall on a Coachella weekend. And although a good number of my friends were interested in going, a lot of them already committed to going to Coachella, so no one else was available to go at the same time that I wanted to.

Obviously, I wasn’t going to let going alone stop me from taking the trip. Going at the time that I wanted to go was more important to me than waiting for someone else to go with me. Also, the prospect of setting my own schedule and being able to decide what I wanted to do at any given moment sounded liked a dream come true after my first international trip (everything was planned by someone else, and I was not a fan).

Alone or not, I was sold. I bought my plane tickets the same day I found out. One paycheck later I bought an eight night stay in a hotel in Tokyo. The paycheck after that I bought my JR Rail Pass and accommodations for a night in Kyoto. Then all the remaining paychecks I made until the time I left would be set aside as spending money for when I got to Japan.

As I said before, Japan was BY FAR the most planned trip I had ever done. When I went to England and France, I was frustrated with the way our schedule was set, and I was certain that I could plan a trip much better. Japan was my way of proving it.

I put together an itinerary that planned my days to the hour, included all price estimates (in both JPY & USD) of every activity and wrote down not only the addresses, but also step-by-step directions to each destination. I even had the names of each place typed in Japanese just in case I ended up having to ask someone for help who didn’t speak English because this way, they would at least be able to read their own language (crazy, right?).

I also learned very basic Japanese phrases, ones that I felt I absolutely needed: arigato (thank you), sumimasen (excuse me), _____ wa dokodesu ka? (where is the…?)

And I was set. Or so I thought.

It’s funny how life throws you curve balls, almost especially when you think you’re prepared for them. I actually think that being more prepared allows for more things to go wrong because you’ve already given yourself a million expectations.

Nothing illustrates this more than my extremely hectic first couple hours in Japan:

When I first bought my plane tickets, there must’ve been a reason why I thought it was good idea to purchase a flight that landed in Japan at 10:30pm. Maybe it was a lot cheaper that way. Maybe I wanted to optimize my number of days and that was the only way to do it. Whatever the reason, I’m positive that from the moment I stepped out of the airport, I thought to myself, ‘Why the hell did I do this?’

Even as I was walking through the airport, seeing mostly everything closed and relatively few other people walking around started to give me a bad feeling. I looked for signs that led to the taxi line and after having walked around a bit, I ended up outside at an intersection with no taxis in sight. There were taxis driving around the streets, but none of the lights on the tops of the cars indicated that they were free; they were already carrying other passengers.

I’d never flagged down a taxi before, not that there were even that many to flag down, but the prospect of it definitely had me out of my comfort zone. Where do I stand? Can I flag one down anywhere? Do I just wave my hand? I crossed the street hesitantly, all of these questions buzzing around in my head, while my eyes skimmed the waiting cars as I passed them in the intersection.

Then I made eye contact with one of the drivers of those cars (who just happened to be driving a taxi). The light on top of his car indicated that it was vacant, and I stopped in front of it (smack dab in the middle of the intersection, mind you) continuing the staring contest that I was having with the driver. He looked at the suitcase that I had beside me and made a gesture pointing his index finger down a couple times: ‘you need a ride?’ I nodded, and he immediately reached over and opened the passenger side door. I rushed over and hurried to put my suitcase in the back seat, but of course the moment I successfully got it in, the light turned green, and his cab was in the very front row of cars waiting to go. I slammed the backside door, jumped into the passenger seat, and barely got my door closed before the driver took off, not fast enough apparently because we still earned a few honks.

After taking a couple seconds to calm down, I turned to look at my co-conspirator. He was an older gentleman, probably in his mid-fifties or sixties, and he drove in a white button up shirt with a tie, slacks, and although I couldn’t see them, I figured he was wearing dress shoes as well. The feature that stood out the most to me though, were the white gloves he wore to drive with. They were like Mickey Mouse gloves, and I up until this point the only time I ever saw someone drive with gloves on was in a movie or on TV. And it was usually elderly women or personal drivers who did it (shrug).

Although my taxi knowledge was limited, I was still aware that what just happened was a very unconventional pick up, and I’m not even sure that it was legal, but regardless I was happy that I was able to get a taxi. Things were looking up.

Then the driver turned to me and began speaking in Japanese. When I responded in English, he responded with more Japanese. Oh boy. Maybe it was wrong of me to assume that, in this part of Tokyo, this close to the airport, with his profession to boot, that he would know at least a little bit of English. But alas, my assumptions were wrong. He knew zero English. And me saying the name of my hotel didn’t help either (turns out it was a widely spread hotel brand, like me saying ‘Hilton’ or ‘Marriott’). I did have the district name written down as well, and I feel like with that information, the driver should have known where to go, but as it turns out, I would soon discover the limited extent of his knowledge.

He was a kind man, don’t get me wrong. And after about fifteen minutes of driving around hopelessly, he pulled over on the side of the road and turned his meter off. I remember thinking to myself ‘please don’t tell me to get out,’ and I imagined myself wandering the dark streets of Tokyo with no cell service and only my suitcase for company. But he only stopped to use his GPS. To which I thought, ‘YOU HAVE A GPS?! HELLO. WHY DIDN’T WE USE THIS EARLIER.’ Still, I sat there patiently, waiting as he slowly typed each Japanese character one by one, his eyes squinting at the iPad sized screen.

Obviously, I had no ideas what the characters on the keyboard meant, but I knew enough to understand that when certain characters became grayed out, and only a few remained black, the keyboard was only presenting you with the option to type names that actually existed. But my driver didn’t know that and kept insistently tapping the grayed out keys, getting more and more frustrated when the character wouldn’t appear. No wonder he didn’t want to use the GPS. Poor grandpa.

I looked at my phone and noted that thirty minutes had already elapsed since we left the airport, and it was nearly midnight. I had plans to get up bright and early the next morning to start my first official day in Japan, and getting to the hotel was taking a lot longer than I originally anticipated. Finally, after another five minutes of grandpa driver mumbling the name of the hotel to himself and pressing more keys on the GPS, he had a Eureka moment and started speaking excitedly in Japanese. He busted a u-turn and drove for about fifteen minutes until I saw a building that had my hotel’s name on it. Hallelujah.

I paid grandpa driver in the yen that I got at the money exchange (he still didn’t turn on the meter from the time that we stopped until we got to the hotel), and when I reached the front doors of the hotel, I peered into the brightly lit lobby, then turned back and saw that he was still waiting for me to make sure it was the right place. He put up a thumbs up, and I returned the thumbs up and waved bye with a big grin on my face. He nodded, himself smiling, and got in his car and drove off.

I walked to the front desk and was greeted by a gentleman who took my ‘hello’ as his cue to speak in English (thank goodness), and pulled out my reservation paper from the FedEx folder I was using to hold my full itinerary, passport, copies of my passport, and $400 worth of yen. He looked over my reservation for a moment before beginning with, “I’m sorry, but…”

The moment he said ‘I’m sorry’ my world shrank a bit. What could possibly be wrong? It turns out that although the hotel was the correct brand, I was at the wrong location. By a mile and a half. I watched, dazed, as he pulled out a map printed on computer paper and highlighted the route I needed to take to get to the correct hotel. I almost laughed out loud when he had to draw a line that went off of the map, and circled an empty spot above the desk, indicating the location of my hotel. I thanked him numbly and walked outside dragging my suitcase behind me.

The exchange must’ve lasted no more than five minutes, but grandpa driver was already long gone.

In hindsight, I probably could’ve asked the front deskman to call me a taxi. But by the time I realized that it was way too late to flag one down (it was almost one in the morning, and there were practically no cars on the road, taxi or not), I had already walked for too long and figured it couldn’t take much longer to walk a mile and a half.

Thirty five minutes later I arrived exhausted, with two of the four wheels of my suitcase damaged by the stretches of cobblestone I occasionally had to cross. I entered slowly and said ‘hello’ with much less enthusiasm as the first hotel. The man at the front desk greeted me with a smile and held up my FedEx folder, asking me almost slyly, “Does this belong to you?”

“Yes, actually. How did you…?” I responded confused.

“You left it on the front desk at the other hotel. They had someone drive it over.”

Of course I did.

And while I spent nearly forty minutes trekking through cobblestones and dark, shady little side streets (not that I ever really felt in danger), my folder had a private driver and probably made it over in less than five minutes. Not to mention the fact that it contained every single important document to me at the time and $400 worth of yen (which, to their credit, was all still there).

But all in all, I was gratefully in bed by 2am. First day (technically night) complete.

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