What Japan Taught Me About Leaving Gaps
Drafted with AI assistance — Claude Code, fittingly — and reviewed by the founder.
For Spain and Paris I built out 15–20 page Google Docs — restaurants booked, museum entry times slotted, transit mapped down to the platform. It worked, in the sense that I didn't miss anything on the list. But by the second week in Paris I noticed I was checking off boxes more than actually looking at anything.
More Room to Wander
Japan I planned differently, mostly because I had to — Kyoto to Lake Kawaguchiko and back into Tokyo isn't something you improvise, the trains and buses need to line up. But I left more afternoons open, and told myself that if something looked interesting, I'd just stop.
Off Route Near Kyoto University
One morning after Ginkaku-ji, walking the Path of Philosophy along the canal, I noticed on the map that Kyoto University was maybe ten minutes off route. No real reason to go — just curious what a Japanese university looks like on an ordinary day. I ended up in the student cafeteria past the lunch rush, maybe eight people left, laptops open, same posture as any cafeteria anywhere. I was hungry, and it felt like the realest Japanese food I'd have all trip — not a menu built for tourists — so I loaded up a full tray. Ended up paying almost triple what the table next to me did; they'd each ordered one bowl, I'd taken one of everything.
The Alley I Didn't Plan to Turn Down
Shinjuku a few days later, I actually had a real errand — buying Onitsuka Tigers. Got them, kept walking, and turned down an alley I hadn't planned to turn down: two people wide, red lanterns, maybe a dozen stalls the size of a closet. Sat at a ramen counter with no idea where I was. Turned out it was Omoide Yokocho, one of the pockets of Shinjuku that survived the postwar rebuild more or less untouched while everything around it got razed and rebuilt. Best bowl of the trip, and I only learned why it mattered after I'd already eaten it.
I don't think the lesson is “don't plan” — bad logistics will ruin a trip in Japan same as anywhere. It's closer to: the plan should get you to the right neighborhood. What happens once you're standing in it shouldn't already be decided.
That's the whole bet behind CityYoYo, too — no fixed stops, no city limits, just narration for wherever you end up.
It's free to download.
