“Why the heck are you going to Japan for your honeymoon?”
That was a question we got a lot when friends and family heard our plans for our post-nuptials. A visit to the land of the rising sun isn’t on everyone’s radar when they hear honeymoon. Italy, Hawaii, Aruba, Bermuda, are the expected answers.
Well, I’ll tell you why. As a small child, during the Attitude Era of WWF (now WWE), I was a huge fan of the small Japanese stable Kaientai. I used to run around my room with the Emporer’s flag, yelling “Evil”, and pretending to get revenge on Val Venis (Choppy Choppy) for his indiscretions. I vowed if I ever went anywhere for a honeymoon, it would be to the land of the rising sun to meet my heroes.
Just kidding, I’m a big fan of the attention-grabbing fake intro, the real reason we decided on Japan is below (but take a minute to watch Kaientai highlights, they were criminally underrated).
How the heck did we settle on Japan?
After getting engaged we did a weekend trip to NYC to celebrate. We tried the world’s largest slice of pizza, visited speakeasies with our friend Ku, and while driving we listened to a book by Anthony Bourdain on audio. In the book, (in between wild tales of drug abuse) the late chef fawned over Tokyo and Japan in general.
Bourdain said if he could visit only one city for the rest of his life it would be Tokyo. His detailed descriptions of the food made our mouth’s water. He spoke at length on the wonders of a trip to Japan with such enthusiasm that Ranna and I were ready to buy a timeshare if he was selling.
We started joking about doing our honeymoon to Japan. Ranna’s favorite food is sushi and Ichiban Hot Pot in Braintree is her favorite restaurant. It would be perfect. I had also watched a Donny Does video on Japan and learned that the customer service there was insane (if you overpaid for something by pennies they would run you down to give you back your change).
There was only one problem, we both had heard Japan was insanely expensive and we were saving for the wedding/our first home. It was a nice daydream, but when you start putting dollars in a spreadsheet, that’s when reality brings you back down to earth.

Or is Japan really that Expensive?
Bourdain put a seed of wanderlust in our hearts for Japan. I started googling trips to Japan and reading about how expensive it really was. I came to learn, like most things, there are levels to Japan and you can do it without being a millionaire.
Japan gets a reputation for being uber expensive because it has the highest concentration of five-star restaurants in the world and top of the line hotels. However, as I read, you could still stay at nice hotels and dine at fine restaurants without breaking the bank. Furthermore, I learned you could play with deer, feed monkeys, and drink beer anywhere; I was sold.
Ranna was pumped to hear Japan was a feasible destination. Early on in the honeymoon discussions, she had expressed her desire to do an untraditional honeymoon with a lot of sightseeing, instead of laying by a pool or ocean. We do that all the time in Nantucket (wow I sound like a douche) and had already been to Hawaii (wow even bigger douche). She was down for something different and was ecstatic that she would get to travel to the birthplace of one of her true loves: Sushi.
Doing something different is in my DNA. I’ve been an annoying hipster my entire life that has to do something “original” or against the crowd. I refused to buy a Northface in high school because everyone had one. I’ve always had a droid and don’t know how to use an iPhone. I quit varsity soccer going into my senior year, when I finally would have started, to do cross country. I got into punk rock and majored in English because I felt like it was an “F you” to the man.
Every girl I knew that got married had the same god dang story on Instagram for their honeymoon. They would be eating at an Italian restaurant and then pan out to the sea to show they were on the coast of Italy. F that. You’re all going to Italy, O-Man and the beautiful new Mrs. O’Day are going to JAPAN! Sayonara!
Also, nothing against all of you that went to Italy for your honeymoon, I’m sure it was lovely, you’re just basic and follow trends. Now go use your new iPhone, zip up your Canadian Goose Jacket, and eat at the new hotspot in Southie: sheep (Editor’s note, wrote that paragraph prior to COVID-19, shoutout to Italy, stay strong!)
Japan: Here we come, but first we forgot our train pass
Still recovering from the whirlwind of our wedding, we sat in the international security line at Logan airport, waiting in a surprisingly huge line for 5am on a Monday. As we slowly moved up in the line, my thoughts began to drift. I thought about how great our wedding was and then I randomly started thinking about a scene from the movie Creed.
In the scene (posted above), Creed gets knocked to the canvas and is out cold. He has a rapid flashback of pivotal moments in his life, takes a big gasp, and gets up off of the ground. I started thinking about what moments would be in my flashback and then suddenly I see the image of our Japan Rail Passes on our dresser, and just like Creed’s gasp, I let out a huge, “Oh shit!”
I give Ranna a look of terror and ask, “You packed the Rail Passes right? They’re in your bag? Please check.” Ranna rapidly checks her bag and we realize we have left the most important part of our trip behind.
The Japan Rail Pass grants you unlimited trips on Japan’s high-speed trains. You can only buy it outside of the country and they do not issue replacements if you lose it. They are the key to how we plan to travel throughout Japan on our honeymoon. Without the passes the trains we plan to take, sometimes a few in a single day, would cost us thousands of dollars.
We had put the passes on our dresser to not forget it, but they ended up being the one thing we forgot to pack. Our first instinct is to jump out of line, grab a cab, and hustle back, but there’s no way we will make it back in time with the security line so long. We then talk about not just traveling as much in Japan, but our hotels are spread throughout the country, and we want to do all the things we had dreamed about.
I decide to call a Hail Mary and frantically call my Dad. I tell him the situation is dire and we need the rail passes brought to the airport asap. He says, “Say no more fam, OMan’s Dad is on it!” (actually probably said, “Ok son, I’ll get them to you as soon as possible.”).
I tell the TSA agent at the front of our line our situation, that we will miss our flight if we get out of line, we’re on our honeymoon, and one of us needs to go and get the passes (forget if I dropped the line I work security too man that makes Ranna cringe). Luckily for us, he was a cool TSA agent and let us stand by the side at the front of the line. Time started to tick down and we prayed for the call from my Dad.
With time running out, my Dad calls and says he’s outside. I call on all the speed from my track days and sprint to meet him. I thank him x 1,000, grab the passes, and make it back to Ranna. With our Japan Rail Passes in hand, we make it to our first flight in the nick of time.
So You Don’t Have Your Passport Eh? Getting Detained by Canadian Border Patrol
We were flying from Boston to Montreal and then from Montreal directly to Tokyo. Due to our first flight being pushed back 4 hours than originally scheduled, we arrived in Montreal early in the morning, with hours to kill before our connecting flight.
After a nice breakfast, Ranna wanted to nap, so I left her with our backpacks and my phone, so I could charge it for our next long flight. I started to explore the airport and went looking for a book to buy. I spent a while reading the back of books in the corner of an airport store. I settled on a book about Canada’s most notorious biker. Since I didn’t have my phone to google the book’s reviews, I wanted to read a little bit of it to see if it was interesting. I was probably in the corner of the store for 30 minutes.
I approached the teller, who was busy on their phone, and got their attention to buy the book. After purchasing the book, the teller asked where I was flying, I replied, “Japan” and they gave me an oh crap look, like when I realized we didn’t have the rail passes.
They told me they needed to call airport security. While I was in the store access to the international area of the airport had been locked off. I was confused and looked outside. Blocking me now from where I had come from was a huge unfolded plastic wall.
A Canadian border agent came on a bike and after learning about my situation called three more agents in. They asked for my passport and I said it was with my wife. They asked me to call her and I said my phone was there also.
They asked if there was anything I had on me that proved I had flown in there today. I luckily had my ticket stubs on me and gave it to them with my driver’s license. One of the guards started to aggressively grill me with questions. I was pissed, all I did was buy a stupid book about a biker, they had locked me in!
The leader then asked his subordinate if he had swept the store like he was supposed to before doing the lockdown. Just then the teller working the register butted in and said I definitely wasn’t in the store prior to them closing the barrier. Pissed, I said, “Run the security tapes back, I’m in the corner of that store the entire time. You were too busy on your phone to notice me.”
More security guards came and I was now getting nervous about what Ranna must be thinking. Frustration coursed through my veins, but I tried to keep my cool because I knew that nothing good would come from me yelling or getting angry with them.
Just when I started imagining being sent to a Tim Horton filled Canadian prison with mooses, guarded by Mounties, one more guard came over. Luckily he had people skills and ended up the most friendly. First, he said they checked the tapes to make sure I had not met with anyone (secret spy O’Day). Then they called U.S. Border Patrol to ask how they wanted to handle the situation. The U.S. said they had to call their supervisors.
At this point, the guards asked if I knew french and said “Wi”, and joked that’s about the extent of it. They then started speaking in French and laughing. One of them got a call with on his phone saying it was from Washington DC and they joked that President Trump was calling about me. The US border patrol finally gave them the green light and they opened up the door to the international area.
I expected Ranna to be worried sick, but when I got to her, she was still laying down and took a deep yawn. After hearing my ordeal she said, “Oh yeah I thought you were taking a while.” Hand in hand, with my laid back wife, we boarded our flight for Japan. The flight took off, and on cue, the guy in front of me reclined for the entire flight.
Arrival in Japan
After our 13 hour flight, we touched down in Tokyo. I felt like we had gone through two of Hercules’s labors to get there, and was afraid the 5 others were awaiting us.
Luckily though, my fears were unfounded, and Japan was the easiest foreign arrival I’ve ever experienced. Tokyo customs was a breeze. They were friendly and pretty much smiled and stamped us through.
Then it was time for the first test of Japanese customer service I had read so much about. I had ordered two Pasmo cards (basically prepaid debit cards that can be used anywhere in Japan and reloaded at 7-11) and rented a wifi hotspot, which would be crucial for us to navigate and post Instagram stories of our strange adventures. There was a post office at the airport I was supposed to pick them up at. When we found the post office, they said they were expecting me and had my package right away. Everything was in order and they also activated our Japan Rail passes.
Everyone was friendly, efficient, and calm (I could get used to that service). While making our way to the train to take us to our hotel we were approached by a film crew. They asked why were in Japan and if we would like to be a part of a TV show. I thought it was something akin to a timeshare scam and waved them off. I would later find out it was a popular national tv show in Japan called “Why did you come to Japan?” where they follow foreigners around and film them experiencing the reason they came to Japan. I had blown our chance to become big in Japan – oh well.
(This is the show we would have been on, if I wasn’t so close-minded)
We made our way to the train terminal and waited for our ride to downtown Tokyo. Any vacation doesn’t really start until you have that first relaxing moment. I took out my Pasmo card and went up to a vending machine on the train platform. It was stocked with beer and I made my selection (you can drink anywhere in Japan, can’t smoke everywhere though). Out came a Sapporo, I cracked it open, took that first sip of cold nirvana, and instantly switched into vacation mode. I smiled to Ranna, with up to no good grin, and said, “It’s time for the O’Day’s to take Tokyo!” She rolled her eyes and said, “Sure babe.”
We made our way to the hotel in downtown Tokyo, checked in (again phenomenal customer service), and went out looking for a late bite to eat. We settled on a tavern nearby and took up seats at the bar. A familiar rock song was playing, that I loved, but couldn’t place it. The bartender saw me trying to Shazam it, came over, and yelled while smiling, “Cheap Trick, Cheap Trick!” I smiled and knew we were at the start of a great adventure.
Tokyo Tourists – Let’s Get Weird. Cat Cafes, Inside Trippy Parks, and Harajuku Girls
We spent the first few days as typical tourists in Toyko. We visited shrines, toured temples, did Virtual Reality at Sega’s Headquarters, experienced smart toilets (big fan of bidets and warming seats), learned no one jaywalks, ate lots of sushi (especially from 7-11, more on that later), and often got lost.






One particular time we got lost, we needed to get to a specific subway and were tight on time before the fish market was to begin. I thought I found it on the GPS and after walking a mile or two later in the heat, instead of the train, I lead us to a subway restaurant (I’m an idiot).
The locals and police were extremely helpful when we lost our way. We would often point on our phones to where we were trying to get to and they would demand to accompany us there (I don’t think that would happen much in Boston, but I do try to repay the favor now. Shoutout to the lost German guy kayaking on ACK this summer. Hope I pointed you in the right direction and not out to sea).
We didn’t get to experience the Tokyo Fish Market in time for the early morning selling, so we missed what all the hype was about. We toured it and had lunch, but it wasn’t anything I’d write home about.
However, while leaving the fish market, we randomly learned about an inside theme park called Teamlab Planets Tokyo. We decided to stop by and it was one of the trippiest experiences of our lives.
TeamLab is an inside, self-guided-park, where each room is an interactive display of art. You will walk into a room with ankle-high water, suddenly digital fish appear, and they move if you touch them. The next room is filled with mirrors that suddenly go dark, flip around, fill with light, and so on. Other rooms included a big bean bag type room and also a room filled with huge balls and if you touch them, they will float right up the ceiling and turn colors.
Besides basically being a psychedelic trip, another crazy thing about TeamLab was there were no guards in any room telling you where to go and making sure you weren’t messing things up. You were trusted to find your way about, have fun, and be respectful. (I think if we brought one here, we might need guards, lots of guards).
Cat Cafe
After TeamLab it was time to experience one of the main reasons that sold us on visiting Japan: a cat cafe.
Cat cafes are exactly what they sound like. You pay the price of admission and enter a cafe filled with cats prowling about. We visited the Mocha Cat Cafe (the same one in the video above) and had a lovely experience.
The place is filled with all types of kitty cats. They come up to you to play or just curiously look at you. Ranna is a cat lover (shoutout to Jada) and was in purry heaven. They also had unlimited drinks and their mocha green tea was to die for, so yummy.

Like most animal loves, I’m always wary of supporting a place that may be harming animals, but all the cats seemed happy and content. Also, while I was there one of the workers was weighing the cats to make sure they were all at a healthy weight.
However, after the cat cafe, we had our first bad experience in Japan at a dog cafe. Unlike the cat cafe, which had plenty of rooms for the kitties, the dog place was basically a small apartment filled with way too many dogs. We wanted to leave right away but the workers pushed the dogs towards us and motioned for us to feed them.
I felt like a piece of scum for visiting the place. I thought of our dog Hunter, who is a rescue dog himself, and wanted to break a window and escape with all of the dogs down the streets of Tokyo. Instead, we fed the dogs, waved off the workers that told us we still had plenty of time left in our visit, and left feeling ashamed of ourselves for visiting the establishment.
After that big downer, we jumped a train to visit Harajuku. Ranna’s a fan of Harajuku style and Harajuku girls. I was intrigued and a bit impressed; I was usually the weirdo in our relationship that liked anime and subcultures, but here was my wife into an obscure fashion genre, that I knew nothing about.
For the uninformed, Harajuku style is a mix of all the well-known Japanese sub-styles, for example, it mixes cosplay, bright colors, cutesy fairy styles, and punk rock clothing. It was also made famous in America by Gwen Stefani with her song “Harajuku Girls.”
We toured Harajuku and had lunch at the famous Kawaii Monster Cafe, where the servers are dressed in the Harajuku style, and the place is an explosion of colors and tastes.
The colorful food reminded me of the lost boys foodfight in the movie Hook. After lunch and taking playful photos with our server (below) we did a walk around the fashion district.
Fashion is king in Harajuku, especially vintage clothes and rare sneakers. It was funny seeing old US college sweatshirts from the 90’s, we all probably had in our closets at one time, being sold for over a hundred dollars in Japan.
I fawned over the rare sneakers and got talked out of paying $400 for a pair of lime green Jordan 3’s you can’t get in the states (kind of wish I bought them now).


7-11 is King in Japan – getting chased down for short changing a guy
We jumped a train back to our area of Tokyo and got ready for the night out. For some reason everyday housekeeping would leave us brand new toothbrushes and little baby bottle of toothpaste. With clean teeth and a sense of joy, we headed out into the bright lights of Tokyo.
After a nice dinner and drinks it was time to make our way home. Every night I would stop at 7-11 for sushi burritos and to grab waters & bottled ice coffees for the next day. This night I decided to test the change story (if you overpaid by a few pennies, they supposedly would run you down to give you the change).
Before I get to the story, let me give you a little background about 7-11 in Japan. They are very different than the ones in the US. Same color scheme, but in Japan, they have fresh sushi (very good, fell in love with their sushi burritos), fresh sandwiches, their own branded beer & alcohol, fresh fried fish and so on.
They are weirdly the main place to get cash out of an ATM in Japan, where you can reload your pasmo card, and also believe it or not, a big hotspot for businessmen on their lunch breaks. They have great customer service, are spotless, and their bathrooms even have smart toilets. You can also find them or their associated brands on almost every corner – they are everywhere and an essential part of Japanese everyday life.
Believe it or not, one of my favorite days of the honeymoon was spent largely in a 7-11. Now before you text Ranna and say you’re so sorry that she had to marry me and spend her honeymoon in a 7-11 in Japan, hear me out.
We had gotten up in the morning at the crack of dawn to take the train to tour a temple and walk a bamboo forest. It was stifling hot outside and we had plans later that day to tour another part of the city. Both of us were tired, hot, and thirsty.
We stopped in a 7-11 to grab drinks and charge our phones. We then basically had a come to Jesus moment, where we both confessed we didn’t want to do the afternoon’s planned activity. It was too hot and we just wanted to relax. So instead we bought a 6 pack, some of their mixed drinks, and spent the afternoon getting tipsy in an air conditioned 7-11. It was a lovely day.
Now back to my change story. As I stated above, I had heard that if you overpay at all in Japan, even by a small amount, they will run you down to give you your change. I decided to put this to the test and while purchasing my waters, ice coffees, and sushi burritos, I made sure to include about an extra 40 cents in various coins.
I left the store and started walking down the street. To my surprise, the 7-11 worker came running out of the store after me. “Holy shit, it worked,” I thought.
I began to smile, but instead of handing me my change he said, “You owe more, not enough money!”
Holy crap, I had shorted him. I apologized and gave the man the correct change. Said a quick, “Arigato” and took my embarrassed self back home.
Thank you for reading part 1 about our trip to Japan. Part 2 and 3 will cover the night life and other cities we visited like Kyoto, Hiroshima and more (plus their hidden gems like Monkey Mountain!).
Preview of Part 2 is below (dropping next week) .
Tokyo Night Life: Ranna finds her new love Ramen, and Oman has a solo adventure + causes yet another controversy
(This video takes place in the bright nightlife of Tokyo)
Tokyo lights up at night. Japan has more than 80,000 bars, and at least 25,000 of them are in Tokyo alone. With so many options, the real question is, where are the best spots to hit?
I’m a big believer that the locals of a destination can show you the best time. They help you avoid tourist traps, show you hidden gems, and give you experiences you would not get on your own as a tourist. With that in mind, I booked us several “Airbnb Experiences” in Japan that included different types of tours.
The first tour we went on was a “Eat/Drink like A LOCAL – Taverns & Ramen” a saki and pork-filled adventure with our host Akira.
More about the Tokyo nightlife and how I ended up on a clubbing adventure with VR Tech Bros next week.
Japan is really a dream country for many. The way it upholds all its traditions at par with modern technology is beyond understanding. Also, we love ramen.
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