Would LOVE recommendations, roughest 29 day itinerary in Dec-Jan

Hi everyone!

I am super excited but also super stressed planning my trip to Japan. Initially I was just going to go and wing it… book hotels as I go but I got increasingly worried that I wouldn’t be able to find accommodations during the holidays or get stuck in a place cause I like it too much. Going from one extreme to the other, I have now done too much research and have this huge list of places I’d like to go…

I’d absolutely LOVE any advice particularly concerning:

1. Places I should definitely go / skip to fully utilize the season I am going (I want to do Winter stuff in Winter). Where I should spend Christmas (I want to eat KFC) and New Year’s (I want to see cultural stuff)
2. Places that are kind of overlapping that I don’t need to see both
3. The order

I am VERY open to moving things around and just dropping places completely. I went from being like eh I’ll go to Tokyo, Kyoto, and Hokkaido, to…. well, this.

For each “range of dates”, I would probably home base it somewhere and then just go from there without much planning. Basically I just want to have a general idea of what I’d like to see and when, just to be able to book accommodations.

I am sure that whatever this ends up being, I will absolutely enjoy the trip!

More context comes after the samples.

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sample 1:

I am partial to this order because I can buy warmer clothes as I go (vs packing it away and lugging it around), and it seems that it matches up with events better (Kyoto & Himeji illuminations, Zao Snow Monsters, asahikawa penguin parade).

dec 11-18: okinawa diving

dec 19: fly to hiroshima, miyajima

dec 20-23: himeji on way to kyoto, osaka, nara, koyasan

dec 24-jan 1: tokyo, kamakura, nikko, hakone, mt fuji, two disneys

jan 2-6: hakodate, otaru, sapporo, niseko, asahikawa (penguins), furano, hiraizumi, sendai, zao

jan 7-8: kanazawa, shirakawago, takayama, nagano (monkehs)

jan 9: tokyo shopping

jan 10: home

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sample 2:

Logically, this is probably smarter because I don’t have to ride the 8hr JRail between Hokkaido and Tokyo twice.

dec 11-18: okinawa diving

dec 19: fly to hokkaido

dec 20-23: sapporo, niseko, asahikawa (penguins), furano, otaru, hakodate, hiraizumi, sendai, zao

dec 24-jan 1: tokyo, kamakura, nikko, hakone, mt fuji, disneyx2

jan 2-6: kyoto, osaka, nara, koyasan, himeji, hiroshima, miyajima

jan 7-8: kanazawa, shirakawago, takayama, nagano (monkehs)

jan 9: tokyo shopping

jan 10: home

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other ideas…

Okinawa at the end??? But yuck luggage and I won’t be able to be like “bye Japan!” in Tokyo.

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some places I am considering scrapping..

* okinawa. I really want to go to Japan because I want to see it when there are still few tourists.. this doesn’t really matter underwater (lol). Also, as mentioned above, I want to do Winter things in Winter. BUT, it does feel like a waste to be in Japan and NOT dive (I love diving). It could even be shortened from 8 days, but I just picked that so that I can just get the 21 day JRail pass and not worry. I could dive in Shizuoka but of course, see different things.
* hakone & mt fuji. I can’t climb fuji in the winter anyways and it seems the view is great from the shinkansen in the winter anyways? expensive. and I’ll see onsen elsewhere.
* hiroshima. the only thing I really want to see over here is miyajima
* himeji. added this pretty much last and don’t know how much better this castle is vs all the other ones i’ll see
* koyasan. bit out of the way and does this overlap with some of the other places i’m going?

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more context..

* I am going on my own, and it is my first time to Japan
* I plan to just bring one carry on. If I find a lot of things I want, I’ll buy a suitcase in Tokyo at the end
* I like more nature/active stuff (theme parks count), I probably won’t even go into temples if you need to pay (maybe one) but admire them from the outside
* But I am also a raging video game nerd (jrpgs and otomes) so will prob want to spend a decent chunk of time in Tokyo
* I can read and listen to Japanese… don’t ask me to speak..
* I’m from Canada so temp wise I am okay. I could technically bring an old jacket and… throw it out… if is it worth it
* I’d like to try staying in a bunch of different types of accommodations – traditional ryokan, temple, farmhouse, homestay, capsule hotel

Thank you so much for any advice at all!!!

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