Level 50 Unlocked: Japan Edition
Turning 50 in Japan Was the Best Decision I Ever Made
Every year I throw my own birthday party. I had this grand plan for my 50th: rent a second line band, roll through New Orleans with friends, big celebration, and a bunch of bourbon.
Then I actually thought about what that would involve. Coordinating flights for a dozen people. Hotel blocks. Itineraries. And I realized I’d be spending my birthday doing logistics for other people instead of actually enjoying myself. So I pivoted.
Last year Jered and I went to South Korea for the first time and it completely blew my mind. I had been low-key nervous to travel to that part of the world for years and had no idea what I was missing. So when the 50th came around, Asia was the obvious answer. Jered would also be celebrating his birthday around the same time, and Gene (from Great American Tailgate) happened to be able to make it work too. Wheee!
Jered put real thought (with the help of AI) into the itinerary and I think they nailed it.
- 5 nights in Tokyo to shake off the jet lag, see the big city, and celebrate Jered’s birthday
- 2 nights in Hakone to decompress from the city noise
- About a week in Kyoto, which everyone told us was the best part (they were right), with my birthday landing here
- A day trip to Osaka
- One night at a temple stay at Eko-in in Koyasan
- Back to Tokyo for any last-minute stuff before flying home
We timed it right in the middle of cherry blossom season, which was either great planning or dumb luck depending on how you look at it.
Tokyo
We stayed near the busiest pedestrian crossing in the world, Shibuya Station, and just wandered. Tokyo is packed and loud and overwhelming in the best possible way.
I even stopped by the Microsoft Japan office to have lunch with some of my counterparts there, which was a cool moment.
I made it out to Senso-ji Temple in Asakusa, which is beautiful even with the crowds.
For dinner one night we went to Gonpachi Nishiazabu, the restaurant that supposedly inspired the fight scene in Kill Bill. Worth it.
Somewhere in the neighborhood we stumbled into a breakfast spot with the best French toast I have ever eaten in my life, run by a one-woman show. Jered is the type who always wants to try something new, and even he wanted to go back. We did. Multiple times.
We also did TeamLab Planets, which is hard to describe. Think Meow Wolf but Japanese. And a lot more barefoot.
Surreal, beautiful, interactive, and then we followed it up with some of the best ramen I’ve ever had at a place I’ll never find again.
Street go-karts were a blast and also slightly terrifying. You’re in a little kart in actual Tokyo traffic doing 70-80 kph on roads where the speed limit is 50 and the guide just tells you to keep up. It was terrifying, but awesome.
We went to a sumo match and I learned that apparently slapping is completely legal and encouraged.
Also found an owl cafe, which is exactly what it sounds like. You hang out with owls. Some of them you can pet. There was also a sloth.
One night we hit Deathmatch in Hell to kick off my 50th birthday week. Everything on the menu costs 666 yen. I bought the entire bar a round of drinks (which ended up costing only ~$20-30).
One more Tokyo highlight: Tokyu Hands. If you don’t know about it, it’s a multi-story department store full of tools, crafts, gadgets, and random things you didn’t know you needed. I discovered it and spent way too long in there.
Hakone
We took the train out to Hakone and the vibe shift was immediate. Quieter, greener, and sitting right next to Lake Ashi with views of Fuji on a clear day.
I turned 50 in Hakone. My birthday breakfast was at a little French bakery overlooking the calm lake. I soaked my feet in hot spring water, ate good food, and just sat there. It was exactly what I wanted. No coordinating, good food and a quiet morning on a lake.
Then we took the train to Kyoto and had dinner with some friends who happened to be in the same city across the world as I was for my 50th birthday. This serendipity was a highlight of the trip for me.
Kyoto and Osaka
Kyoto lives up to the hype. We heard from pretty much everyone before we left that it was the best part of Japan and they were not wrong.
I visited the Arashiyama Bamboo Grove, which is genuinely beautiful.
I also went to Iwatayama Monkey Park nearby, which is a long trek up a hill above the city and has monkeys roaming around freely. I got to watch monkeys be mischevious and run around and eat snacks and just be monkeys. It was delightful.
I took a ramen-making class while we were in Kyoto. I had no idea how much work actually goes into a good bowl of ramen. Now when I eat it, I have a new appreciation for it. (and glad I don’t have to make it myself)
I had been obsessing over Japanese knives before the trip started and made it a mission to find the right ones. We hit no fewer than ten knife shops across Tokyo, Osaka, and Kyoto. I walked into tourist trap after tourist trap. Finally found a small shop in Kyoto called Kosaka Hamono that felt completely different. He had his name personally engraved on the knives because his friends made them specifically for him. He showed me how to sharpen them properly before I left. I’ve been using those knives at home constantly since I got back. They’re beautiful and scary sharp.
The Yamazaki Distillery was a highlight for the whisky portion of the trip. We sampled a lot of Japanese whisky over three weeks and Yamazaki was the obvious anchor.
Osaka was a day trip and was mostly about eating. Sadly we didn’t explore much as my allergies were bugging me hard and I didn’t bring my jacket, so I was pretty miserable.
We also made it to the Nintendo Museum just outside Kyoto, which opened in late 2024 and had to submit for a lottery as tickets were genuinely hard to come by. Photos weren’t allowed inside past the entrance, but it was a really fun trip down memory lane.
Our last night in Kyoto we went to a distillery sampler that I have no idea how we found. Lots of samples, very friendly people, and a great way to end the Kyoto portion of the trip.
Koyasan
We rented a car to make the temple stay work, which turned out to be a great decision for more than one reason. Eko-in in Koyasan is a Buddhist monastery that takes guests. The monks serve you food and show you how to meditate and participate in this morning ceremony.
At night they walk you through Okunoin Cemetery, which is ancient and massive and lit by stone lanterns.
It has a completely different feeling in the morning light when you see it again on the walk to the main hall.
Having the car also let us stop through Nara on the way back. Everyone talks about how the deer in Nara are graceful and serene. And they are. What nobody tells you is that the second you pull out a deer cracker they will absolutely mob you. Graceful and persistent.
Returning the car was a bit anxiety inducing as we had no idea how to work the pump. But thankfully Google Translate got us through it.
The Food (and the Beef)
I ate more beef in three weeks in Japan than I had in the previous year in the US. It’s reasonably priced over there and it’s good. I also lost weight somehow. Japan’s transportation system will do that to you. You walk everywhere.
The Part That Stuck With Me
When I was planning this trip I thought I was just replacing one birthday plan with another. But it turned out to be something more than that.
I traveled to the other side of the world with two really good friends, made new ones along the way, and ran into people I hadn’t seen in years on the exact day I turned 50. I went to a place I had never been, did things I had never done, and came back with knives I will use for the rest of my life.
For a birthday that felt like it should be heavy and significant, it turned out to just be really, really good. I think my twelve year old self would be pretty happy with how things turned out.
