Japan Itinerary suggestion - Dec 14 to Dec 25

Dear All,
I am travelling to Japan with my 11 year old son. I am planning on getting the JR East nagano pass. Below I list my plans till Dec 20. I need suggestions for Dec 21 to Dec 24. We would like to visit a snowy area on the main island same as Tokyo. We like good food, scenery and onsens. Please help me, thank you.

Dec 14 - Arrive Narita and go to hakone - Pass Day 1, overnight Hakone
Dec 15- Hakone day visit and Odawara castle. Overnight at Odawara
Dec 16 - Kamakura day visit . Overnight at Tokyo
Dec 17 - Tokyo day 1
Dec 18 - Tokyo day 2
Dec 19 - Tokyo day 3
Dec 20 - Gala Yuzawa - Overnight not booked, Pass Day 2
Dec 21 - ?
Dec 22 - ?
Dec 23 - ?
Dec 24 - ?
Dec 25 - Flight back home via Haneda Airport 11pm

Thank you!

Regards
Sylvia

I usually think of an itinerary, by listing destination candidates, making a feasible itinerary, and finally checking a possible use of passes. If you start from the pass, that could make you a blind to your true needs.

Anyway, the best season for skiing is in January. It could be too early to go to Gala on Dec 20. I would put any ski resort in the later part of the itinerary as the flight permits. Gala is basically a day trip ski resort. There are better ski resorts in this region. Most popular ones are Naeba/Kagura in Yuzawa, Shiga Kogen, Nozawa Onsen, and Hakuba. You state onsen. So, maybe Nozawa Onsen could be your best to choose. If you are interested in Snow Monkey Park, you may select Shiga Kogen, instead. Those are in the same area. From the onsen side, one of the most popular onsens in this region would be Kusatsu. There is Kusatsu Onsen ski resort. In its neighborhood, there is Manza Onsen Ski resort. Check the following for more.
https://snow.gurunavi.com/
http://www.snowjapan.com/japan-ski-resorts/search
http://www.nozawaski.com/en/
http://en.shigakogen-ski.com/
http://www.hakubatourism.jp
http://www.e-yuzawa.gr.jp/english/
http://www.princehotels.com/en/ski/naeba/
http://www.princehotels.com/en/ski/kagura/
https://www.kusatsu-onsen.ne.jp/
http://www.princehotels.com/en/ski/manza_onsen/

If your interest is more into life with snow rather than in ski itself, you may go around Niigata. Go to the north such as Tsuruoka, near Sakata? Or, with an additional Sado Niigata Pass, you could visit Sada Island.
http://enjoyniigata.com/en/index.html
http://experiencetsuruoka.com/
https://sado-niigata.com/pass/
http://www.sadokisen.co.jp/language/en/

You list Odawara castle, but a more popular castle in the area is Matsumoto castle. It is on the way from Shinjuku to Hakuba ski resort.
http://www.matsumoto-castle.jp/lang/

The pass covers far down to the south; Shimoda on Izu Peninsula. There is a chain of popular onsen resorts, Atami, Ito, and more.
http://www.shimoda-city.com/#we-page-home
http://itospa.com/ito-city-english-tour-guide/
http://travel.ataminews.gr.jp/en/

Hi Luisjp,

Thank you so much for your recommendation! I am not going to ski at all, more like snow play and sledging only. Nozawa onsen seems to be very attractive.....and yes Matsumoto castle is stunning! I wasn�ft aware the pass would cover that .....perhaps I would include that as a stopover before moving down south to Ito or Atami. I am currently going through all the links you stated. What do you think about karuizawa? I would love to hear your thoughts on that. Thank you once again. 🙏

Then, it might be better to stay in residential areas in snowy regions, or at a smaller ski resort for locals. Here is a mean snow coverage map of Japan in Dec. Promising regions are borders of prefectures.
http://www.data.jma.go.jp/obd/stats/data/mdrr/atlas/snow_cover_12.pdf
The current snow condition will be reported in this map.
http://www.data.jma.go.jp/obd/stats/data/mdrr/snc_rct/index_snc.html
Cumulative snowfalls are here.
http://www.data.jma.go.jp/obd/stats/data/mdrr/snc_rct/alltable/smsnd_s...
Here is a pickup with the average yearly snowfall more than 1000 cm.
1768 Sukayu Lake Towada
1625 Hijiori Yamagata Shinkansen
1399 Oisawa Yudonosan
1364 Sumon JR Tadami Line
1358 Tsunan JR Iiyama Line
1330 Horokanai JR Soya Line
1327 Otoineppu JR Soya Line
1313 Shumarinai JR Soya Line
1303 Tadami JR Tadami Line
1220 Horonuka JR Rumoi Line
1218 Nozawa Onsen JR Nozawa Line
1213 Hinoemata Oze
1199 Sekiyama Myoko
1181 Yuzawa Joetsu Shinkansen
1167 Tokamachi JR Iiyama Line
1164 Fujiwara Joetsu Shinkansen
1073 Yuda JR Kitakami Line
1072 Kimobetsu Lake Toya
1056 Nango JR Tadami Line
1054 Kutchan Niseko
1054 Koide Joetsu Shinkansen
1044 Shirakawa Takayama
1034 Oguni JR Uetsu Line
1024 Fukagawa Asahikawa
1023 Daisen Tottori
Judging from this, I could nominate Nozawa Onsen and Yuzawa Onsen. I believe Kusatsu Onsen could a rival. Kusatsu and Atami would be the top two onsens in the Kanto area. Kusatsu does not prepare a good English site but at YouTube.
https://www.youtube.com/watch?v=XYpyyWJRvMI

Karuizawa is a good resort, but it is basically for a summer. No snow would be expected in Dec. Moreover, it is relatively new, meaning a somewhat westernized resort town. I could say a set of Kusatsu and Karuizawa in summer would be one of the ideal course to try.

The pass also includes Nikko and Kinugawa. Kinugawa onsen is rather popular.
http://nikko-travel.jp/english/

Between Fuji-Hakone-Izu and Tokyo, there are Enoshima-Kamakura and Yokohama.
http://www.fuji-travel-guide.com/news-item/ohmuroyamaandlift/
http://www.discover-fujisawa.jp/
https://www.city.kamakura.kanagawa.jp/visitkamakura/en/index.html
http://www.yokohamajapan.com/

I might take a course of Narita-South-Tokyo-North-Haneda for more snow.

Dear Luisjp,

Thank you very much for helping me. I�fve finalised the plan as below:


Japan Itinerary suggestion - Dec 14 to Dec 25 2017/10/20 14:07
Dear All,
I am travelling to Japan with my 11 year old son. I am planning on getting the JR East nagano pass. Below I list my plans till Dec 20. I need suggestions for Dec 21 to Dec 24. We would like to visit a snowy area on the main island same as Tokyo. We like good food, scenery and onsens. Please help me, thank you.

Dec 14 - Arrive Narita and go to hakone - Pass Day 1, overnight Hakone
Dec 15- Hakone day visit and Odawara castle. Overnight at Odawara
Dec 16 - Kamakura day visit . Overnight at Tokyo
Dec 17 - Tokyo day 1
Dec 18 - Tokyo day 2
Dec 19 - Tokyo day 3
Dec 20 - Yuzawa onsen
Dec 21 - Kusatsu onsen
Dec 22 - Kusatsu onsen
Dec 23 - Nozawa onsen
Dec 24 - Nozawa onsen
Dec 25 - visit Matsumoto castle on the way back to Haneda.

We are so excited and even thinking of learning to ski at Nozawa!

Thank you!!! Thank you!!!🙏

Regards
Sylvia

I prefer to go to Kusatsu, Yuzawa, and Nozawa in this order, in order to see snowy areas more, may be up to the Japan Sea. The pass covers such.
https://www.jreast.co.jp/e/eastpass_n/

https://goo.gl/1aDYwZ
https://snow.gurunavi.com/guide/htm/r0038ens.htm

https://goo.gl/5BMbsV
http://www.e-yuzawa.gr.jp/english/yuzawa-access.html

https://goo.gl/1DMYGi
http://www.nozawaski.com/winter/en/access/

https://goo.gl/PJ7TYV
http://www.matsumoto-castle.jp/lang/eng/access