Advice for a 14 day trip in December

Hi,

Me and my husband are travelling to Japan for the first time, reaching Tokyo on 24th Dec 2019. We are flying out of Tokyo on 6th Jan 2020. We willbe using 14 day JR pass. Below is our itinerary:
1) Tokyo-4 Nights- 24th Dec to 28th Dec (Staying in AP Shinjuku)
Day 1: Tokyo full day city tour visiting all popular suburbs shopping, some temple visits etc
Day 2: Disney Sea
Day 3: Visit Kusatsu onsen-using JR train from Ueno station to Naganohara-kusatsuguchi and then a
JR bus Kanto . Back to Tokyo same night
2) 28th Dec Hakone: 2 nights- 2 or 3 day Hakone free pass
Day 1 Leave for Hakone from Tokyo using the Romance car, sight seeing Open air museum, cable car, pirate ship etc.
Day 2: Continue sight seeing in Hakone (anything special recommended that we can include??)
3) Kyoto/ Osaka 3 nights: Leave from Miyashima to Kyoto arrive on 30th Dec using Bullet train. Haven't worked out proper itinerary yet but plan to visit some temples, spend a day in Osaka and visit Nara( Again any recommendations that we can include?).
4)Kanazawa- 2 nights - Arrive in Kanazawa on 2nd Jan - sight seeing in Kanazawa.
Visit Shirakawago on 3rd Jan as a day trip (Will the buses be operating since it is New Year holidays or
should we rent a car? Will the village be open for sight seeing, can't find enough information online whether the popular spots well be closed.
5) Takayama: Arrive in Takayama and spend a night on 4th Jan
6)Leave for Tokyo on 5th and spend a night.

I just want to double check is it worth buying the 14 day JR pass or should be buy the tickets seperately. We plan to use trains for most part of our journey

Thanks

We plan to use trains for most part of our journey


Note that with a JR pass you can only use JR trains! Not any trains. Ie Romance car you need to pay separately unless you change plan and go by JR to Odawara (which is possible but it is an other route). Also jr Pass doesnft allow you to take Nozomi Shinkansen and to make seat reservations BEFORE you arrive in Japan.
Youfll be traveling in a very popular period and on some days trains out of Tokyo and then back will be very full. Ie all places reserved. So it would be best if you reserve online once the reservation opens (I think a month before). But you can do that only if you donft have a jr Pass. The other thing to consider is if you need 7 or 14 days. If you take romance car to Hakone, you could start the jr Pass only on the day you leave Hakone and that should still bring you back to Tokyo in 7 calendar days. So it depends if the trip to Kusatsu onsen makes the difference. Use hyperdia or google maps to calculate.

For Disney Sea there is crowd calendar I would check, as Ifd think your dates will be very popular.

Enjoy your trip to Japan!

One hot mess of an itinerary.

Seven towns/cities in 14 days. Crazy.

First time to Japan only one day in Tokyo?

Only two full day in Kyoto but wanna do Kyoto Osaka and Nara. You need four days minimum.

I'd drop Kanazawa Shirakawago and Takayama. And do one night at Hakone. And it should work.

14 day jr pass wont pay itself off.

Also a lot of things are closed a few days before and after the 1st. So plan accordingly.