Japan (Tokyo / Osaka) for my son's senior trip in 2026

I just finished planning a extensive trip to Japan heading out in November. Flying into KIX (Osaka) and leaving out of HND (Tokyo). Staying a week in each. Happy to answer any questions.

I'd advise planning your flights into HND/NRT very carefully. If you land in the morning (usually HND for *A), you have to keep yourself awake for 12 hours ... when the bed is right there. I prefer to land a little before 1500 from IAH into NRT. That way, 90 minutes for the bus, some unpacking time, dinner, and then pass out just after dark. I'll wake up at 0300 the next morning, but then I'm on Tokyo time in one night.

It's going to be much hotter than you expect, especially in Tokyo.

Why wouldn’t you do Kyoto in between?

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He doesnt want to do that.

He wants to go to the beach WITHOUT HIS DAD and look at bikinis.

Moms and Dads dont belong on Senior Trips.

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This deserves more downvotes and 0 upvotes.

It depends on what you like.

Osaka is more similar to Tokyo in ways, a large populace city. The main tourist area is different in that it has the canal and it’s considered more of a foodie city, with different culinary traditions than Tokyo. Osaka is more relaxed than Tokyo by all accounts and a bit friendlier.

To be clear one of my friends who has been LOVES Osaka and likes it more than anywhere else in Japan. I have not been, I have just been researching an upcoming trip for almost a full year.

Kyoto is more about culture. It’s one of the cultural hubs of Japan, with plenty of temples and winding alleys, bamboo groves and geisha. It’s still a big city but much more tourist and tradition focused than Tokyo or Osaka which have more business interests.

It’s all about what you and your son want to do in see. If he’s more about theme parks and fast paced action then maybe a day trip to Kyoto and Nara is fine. If he wants contrasting cultural experiences than maybe you want Tokyo/Kyoto with a day/night trip to Osaka. Train between Kyoto and Osaka is pretty quick.

Do your research. Watch YouTube videos and TikTok’s.

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Kyoto is like a 20min train ride from Osaka. So your base can be Osaka but you can do both Osaka and Kyoto at the same time if you want

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There's a Shinkansen that does it in 12. So absurd.

Not as many timings as the slower option though.

For OP, you should spend time in both. And if you need to be efficient, you can easily start in Kyoto, head to Nara for a while, and then on to Osaka. Kyoto has a LOT of temples, and I've seen a lot of temples on Asia, so don't feel compelled to see every one. Pick a few. The market there is a fun diversion, and there's a river cruise outside the city as well that ends nearish the bamboo forest area, and so on.

You could probably train down from Tokyo and get two full days in Kyoto and accomplish a lot. Do the Nara day trip on the way to Osaka, then spend two days down there. That's 5 days of your trip. Day 6 is heading to Tokyo, and then finish off your trip from Tokyo base. Tokyo is so big you probably need 3 full days to get a taste of the major areas. You're all dudes so you can more in a day. You have one day potentially to go off to Nikko or Kamakura. I probably wouldn't try to squeeze Hakone (I tried that as a stop on my way from Kyoto to Tokyo and the Hakone loop took longer than expected). But whether you day trip from Tokyo or not, that's a "know yourself" decision.

Couple other ideas.

1) There are flights that do land at Osaka (KIX) so you could start there and work your way back.

2) When time is really an issue, I landed at Haneda and was on the Shinkansen (from Shinagawa station) within an hour of arrival on my way to Kyoto. I don't mind pushing through the first day. (I had Haneda arrival and departure and tend to put my departure city on the backend of trips as a preference).

See I enjoyed Tokyo more than Osaka. I enjoyed Osaka and kyoto the same and kinda just think of them as the same place for visiting purposes. I would stick the the OP plan. It’s solid especially for first timers

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This deserves more downvotes and 0 upvotes.

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Yeah agreed that was a pretty shitheaded reply. We just got back from taking my 17 yr old son to Amalfi coast /florence/Rome for his senior trip and he had the time of his life. He also went to Destin on a trip with his buddies for a more “senior trip” experience. Pretty sure if he’s spending the coin taking his son to Japan it’s prob not out of pure randomness. Sounds like a great time for all.