What 3 Trips to Japan Taught Me
TLDR: Three trips, five cities (Tokyo, Osaka, Kyoto, Sapporo, and Kinosaki Onsen), and more miles walked than I care to admit. Japan is incredible and very plannable, but you need to know the right things going in. Here's what those three trips taught me: some of it’s practical, some of it’s the kind of stuff you only figure out by messing it up first.
You will walk an insane amount. Plan for it.
Day one of our first trip, we logged 11.27 miles. On accident. We were not prepared.
By trip three, I had a system: two pairs of comfortable shoes rotated daily, toe socks (they completely solved the blister problem I experienced on trips one and two), and a hotel room with a tub so I could soak every night. Some hotels even leave bath salts out for you! If yours doesn't, hunting for some at the convenience store is a perfectly pleasant errand.
Your feet will determine the quality of your entire trip. Don't underestimate this one.
The "tourist" version of everything is rarely the best version.
Sensō-ji in the middle of the afternoon is a crowded souvenir gauntlet. Sensō-ji at night is genuinely magical. Same temple, completely different experience.
Fushimi Inari at sunrise (like, actually at sunrise) is one of the best things I've ever seen. The crowds hadn't arrived, the light was unreal, and we had stretches of the torii gates almost entirely to ourselves.
The pattern held everywhere: go earlier than feels reasonable, or go after dark. Japan rewards the people who show up at weird hours.
Logistics are not the hard part, but they're worth getting right.
Everyone acts like planning a Japan trip is this massive undertaking. It's not, once you know a few things:
Skip the physical Suica card. If you have an iPhone, set up a digital one in Apple Wallet and tap in and out.
Get an eSIM. Pocket wifi is unnecessary at this point.
Book the Shinkansen ahead of time. Splurge on the Green Car for longer routes. It's worth it!
If you're moving between cities with more than a carry-on, ship your bag from hotel to hotel. Your hotel will help you arrange it.
None of this is complicated once you know it. It's just the stuff nobody tells you upfront.
The bar-hopping tours are not cheesy. Book them anyway.
I was skeptical the first time. I've now done them in Shinjuku, Shibuya, Kyoto, Osaka, and Sapporo. Every single one was a highlight. They take you to tiny local spots you'd never find on your own, you meet other travelers (or, if you’re like us, you’ll luck out with a “private” tour because other travelers don’t show up), and they do all the work of navigating the izakaya experience for you.
You'll want to go back. Budget for that now.
Trip one was Tokyo and Osaka. We got home and immediately started talking about trip two. Trip two was Tokyo, Kyoto, and Kinosaki Onsen. Trip three was Tokyo, Sapporo, and Kyoto again.
Japan is not a "one and done" place. It's a place you return to and slowly understand better. Every trip, I've gotten a little faster, a little more confident, a little more willing to wander without a plan.
The best investment I made wasn't in the flights or the hotels. It was actually learning how to travel there well.
The guide that has everything else.
After three trips and more planning hours than I want to admit, I put together a full Japan 101 guide: every logistics detail, city-by-city highlights, my actual Google Maps for Tokyo, Osaka, Kyoto, Sapporo, and Kinosaki Onsen, a real cost breakdown from our first two-person trip, and links to everything I've actually booked. The Notion guide includes a custom AI skill for Claude. Drop it into Claude, and it'll answer your Japan planning questions and build you a personalized itinerary based on everything in this guide.
It's the guide I wish I'd had before my first trip.
Use code KATIEFRANKMARKETING for $5 off.
Katie Frank is a B2B SaaS growth marketer based in Birmingham, AL. She writes about marketing and travel at katiefrankmarketing.com
