Itinerary check: 3 weeks in Tokyo, Kyoto and Chubu over Christmas and New Year’s

My bf and I are planning a Japan trip from Dec 18th to Jan 7th. It is the first time in Japan for my boyfriend, while I’ve visited the country ten years ago for 6 months. We’ve booked our plane tickets and all hotels, Airbnbs and ryokans already, but might change some hotels. We planned to spend New Year’s eve in Tokyo in order to avoid the crowds by traveling in the opposite direction.

Dec 18th

Arrive in Narita Airport at 5pm, head to our hotel in Asakusa (Skyaccess), get some food

Dec 19th

Tokyo: Asakusa, lunch at Wantei Kikko (?), take a walk to Akihabara, see some christmas illuminations in the evening somewhere

Dec 20th

Leave early in the morning for Hakone, spend the day in Hakone and stay in a ryokan in Gora

Dec 21st

spend the day in Hakone, leave in the afternoon and take the shinkansen to Kyoto. Arrive in Kyoto in the evening, check-in and take a walk/have a snack in the neighborhood

Dec 22nd

Kyoto: Eastern and Central Kyoto, railway museum (?)

Dec 23rd

Kyoto: Arashiyama, maybe rent some bicycles, bamboo forest, monkey park, Sagano scenic railway (?)

Dec 24th

Kyoto: Northern Kyoto, Kibune (?), KFC or nice dinner for christmas

Dec 25th

Kyoto: early morning hike to Fushimi Inari and Oiwa Shrine
spend the afternoon and evening in Osaka (Dotonbori and possibly teamLab Botanical Garden)

Dec 26th

Kyoto: day trip to Nara

Dec 27th

Leave Kyoto around noon and take the train to Gujo Hachiman

Dec 28th

Gujo Hachiman

Dec 29th

Take the bus from Gujo Hachiman to Takayama, spend the day in Takayama

Dec 30th

Takayama, maybe visit Hida Furukawa. Depending on the weather/if it snows we might take a day trip to Shirakawago

Dec 31th

Take the train to Tokyo, check-in (hotel is located in Shinjuku), go to a department store and try to get some osechi or just normal bentos for Jan 1st. Not sure yet how exactly we want to spend New Year’s eve, maybe getting drunk in the hotel room and take a night walk after midnight

Jan 1st

Tokyo: hatsumode, relax, Shichifukujin Meguri or just walk around with no plan, Shinjuku Metropolitan Building in the late afternoon

Jan 2nd

Tokyo: day trip to Okutama, hiking

Jan 3rd

Tokyo: day trip to Kamakura with a short stop in Yokosuka on the way back (bf is a huge Shenmue fan and wants to see Dobuita street), dinner at Navy Burger (?)

Jan 4th

Tokyo: Shinjuku, Shibuya, Nakano Broadway

Jan 5th

Tokyo: free

Jan 6th

Tokyo: do some last shopping and do some things we’ve missed

Jan 7th

Flight back at 10 am

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I have a few questions:

– Are stores still closed on Jan 2nd and 3rd? If so, the Kamakura trip can be moved to Jan 5th or 6th
– I’ve checked the JR pass calculator and it looks like the JR rail pass is not really worth it. Or am I missing something? I think we would prefer the flexibility by buying tickets for the Nozomi shinkansen or using the private railways for the trip to Nara
– Is the Sagano scenic railway worth it in december?
– Any recommendations for bookshops that have a good selection of study books (especially graded readers)?
– Any recommendations for restaurants in Takayama and Gujo Hachiman?

Thank you in advance!

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