First-time planning a high-quality trip for my group – we are also first-timing jp during Christmas->NY. Appreciate any checks on my itinerary :)

Budget: around $2k max per person (9 of us… I know this will be hard as well based on research)

Interests: VERY wide range of interests in the group. very difficult to plan for – drinkers, early sleepers, chill relaxers, partiers, shoppers, foodies, anime lovers, we have it all.

I have planned roughly based on geographical proximity but my planning quality definitely dropped after tokyo. Could use any help I can get on what I may be over/underplanning as well as suggestions of what to do during empty time as my entire group is very inexperienced with japan as well as planning trips in general.

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* Dec 23 Tokyo:
* Morning: Yoyogi Park & Meiji Shrine
* Afternoon: Harajuku, Omotesando Street ->Aoyama -> Roppongi -> Tokyo Sky Deck
* Evening: Omoide Yokocho, night out (new york bar?)
* Dec 24 Tokyo:
* Morning: Free Time in Shinjuku (where we are staying)
* Afternoon: Akihabara -> Ueno Park -> Dinner at Kisoji
* Evening: Nakamise Shopping Street, Senso-Ji Temple, Asakusa
* Dec 25 Tokyo:
* Gyoen National Garden + free time
* Dec 26 Tokyo:
* Morning: Tsukiji Fish Market -> Ginza
* Afternoon: Ginza (what is there to do specifically here?), shopping, maybe an onsen? -> Shibuya Sky at sunset
* Evening: Dinner at Katsukichi Bodaichu -> Dogenzaka Nightlife
* Dec 27 Osaka:
* Morning: Transit to Osaka
* Afternoon: Umeda Sky Observatory at sunset
* Evening: Dotonbori -> Namba
* Dec 28 Osaka:
* Morning: Nara -> Todai-Ji, Nigatsu-do & Sangatsu
* Afternoon: Nandaimon -> Deer Park -> Kasuga Taisa Shrine -> Naramachi
* Evening: Omurice in Osaka -> Dotonbori / Namba
* Dec 29 Osaka:
* Morning: Osaka Castle, Shinsekai
* Afternoon: Shinsaibai
* Evening: Kobe Beef restaurant? More dotonbori / namba probably not sure what else
* Dec 30 Kyoto:
* Morning: Transit to Kyoto
* Afternoon: Pontocho Alley, Kiyomizu Dera & Otowa Waterfall, Philsopher’s path & Ginkaku-ji, Nishiki Market:
* Evening: ???
* Dec 31 Kyoto:
* Morning: Fushimi Inari Taisha
* Afternoon: Arashiyama Bamboo Grove, Tenryu-ji Temple, Kinkaku-ji
* Evening: Onsen (Tenzan no yu), ??? for new years evening?
* Jan 1 Kyoto/Tokyo:
* Morning; i know its tradition to shrine/temple visit but we are checking out at 10am so not sure how to plan this.
* Afternoon: Transit to Tokyo -> Free Time
* Evening: Teamlab Planets -> ??? night out I guess