Feedback on our 10-day itinerary to Japan

Hello, Its our first time to Japan as a family. I've been there on business before briefly so a little familiar but didnt really travel much then. Wondering if people think if this itinerary is too aggressive. We are landing December 29th afternoon in Tokyo and returning Jan 7 evening, are a family of 4 with 2 teenage boys - so fairly mobile and active.

Day 1: Night in Tokyo after landing.

Day 2 : Day and Night in Tokyo

Day 3 : Ski Trip (still wondering where?)

Day 4: Skip Trip (back to Tokyo and onto Kyoto). Lodging in Kyoto

Day 5 and 6 : Kyoto

Day 7 : 0.5 day Kyoto and then to Osaka (reach by early afternoon to give us half day there)

Day 8: 0.5 day Osaka and then evening to Koyasan for dinner at Temple

Day 9: breakfast in Koyasan and afternoon towards Kyoto to Tokyo. Night in Tokyo

Day 10: All day in Tokyo before heading to Narita in the evening (7pm flight)

Any suggestions? We generally dont like to do too many places in one trip so I am working on cutting this down. Help me :)

Thanks much for your help !

Traveling between 12/31 to 1/3 requires special attention.
Read here: https://www.japan-guide.com/e/e2276.html
My recommendation is to stay put on 12/31 and 1/1.

Your last statement contradicts your itinerary. You are going to too many places and perhaps not factoring transport and transfer times. A ski trip makes me think your from a warm-weather climate. Is this imperative in your itinerary? If not, I would drop it. Maybe Echigo-Yuzawa is close enough, but elsewhere would be too much of a drain on your time. I would drop Osaka and perhaps leave for Koyasan from Nara. If you�fre doing, Tokyo, no need to do Osaka. But I still think it�fs too much for the time you have. How are you going to handle your luggage between accommodations?

I would cut either Koyasan or the ski trip.

If you go for skiing I think Iwappara or Gala Yuzawa makes most sense as they are so easily reachable by Shinkansen from Tokyo.

I personally still have to discover the attractiveness of Osaka. Although I am there for several weeks each year I tend to spend my free weekends outside of Osaka. Eg currently I am in Iga Ueno.

Dinner at the temple in Koyasan is likely a Very early affair. Eg 17:00. Plus it gets dark really early. Now it gets dark at 17:00. In winter even earlier. So you will not have a lot of time to see anything in Koyasan if you only arrive in the afternoon. This if Koyasan stays on your schedule I would try to get there as early as possible on your day.

Enjoy your trip to Japan.

Like the others, trying to do a ski trip at the end/start of the year is very dicey. Gala Yuzawa would be one of my first ideas as well, since it is so close and the Tokyo Wide Pass can save you some good money. But can you even find accommodations this late, without needing to travel in a long way?
It may be too late to try it. At any rate, you are not giving yourself much time in Kyoto. For Day 7, you could just skip Osaka entirely (or go there in the evening, after a day of sightseeing in Kyoto) and go see Nara. It was also a former capital and has some of Japan's very best.
https://goo.gl/LfvWnL

For Day 8, I suggest just skipping Osaka in the morning and go straight to Koyasan. As said, the daylight hours are very short and with your limited time, you won't be able to see it all. No matter what though, do not miss the Okunoin Cemetery.
https://goo.gl/uAi9oX

Look into getting a Koyasan World Heritage Ticket.
https://www.japan-guide.com/e/e2358_012.html
Going from Koyasan to Tokyo will take you a minimum of 5½ hours.

Thanks everyone for your suggestions - its very helpful. I am going to research/discuss-with-spouse further and might post more questions.

The reason for interest in "Osaka" is food. I've been doing some reading and it seems Osaka is the food capital/kitchen of Japan. My sons are very interested in food experiences there and the thought was to find more authentic food experiences in Osaka than the touristy places in Tokyo and even Kyoto. The other thought was that since Osaka isn't really on most tourist itinerary - it'd be a bit more relaxed way to explore a "bigger city" as opposed to Tokyo.

I would agree with the majority that has already been said. Too many locations for ten days.

Osaka and Kyoto are 30 minutes apart. No need for two hotels.

I would do Tokyo for 4 days. Kyoto for 4 days. And one other location for 2 days. Being the time of year that you are traveling, you should see snow at most locations. So if going to a ski resort is just for seeing snow. Then I would omit it from the itinerary. Or add a day to Tokyo and just day trip it. Which then gives you time for Koyasan.

Osaka is very popular because a lot of people want to eat there and it is very very very popular as a shopping destination. Last time I visited parts of Shinsaibashi area 2 years ago, it was more crowded than Tokyo Disney was on the same trip.

I'm not sure what sort of food your teens are interested or hoping to find that is only available in Osaka.

Personally, if it were me, I would probably plan to do just a 10 day trip to the Kanto area. It would make it easier to fit in a ski trip and would visit Kamakura to see temples and shrines. I like Kyoto and I like Kansai, but sometimes it's not worth it to try to squish it into a limited itinerary, particularly around New Years which has its own complications.

Thanks everyone for helpful posts. So far, the impact of your feedback has been

-> We wont do skiing
-> We will stay put in the same place on Dec 31 and 1

New Itinerary that we are considering:

Dec 29th night : Tokyo
Dec 30th afternoon : Head to Kyoto
Dec 30night/31/1 night: Kyoto
2-3-4 : Osaka/Nara/Kayosan (1 night each)
5: afternoon : head to Tokyo
5 night through 7 afternoon : Tokyo
7th evening : flight back to Texas from Narita.

Is this still too aggressive? Should we consider cutting Osaka or Nara or maybe reduce 1 day from Tokyo on the way back?

Thanks again!

You don't have to move hotels between Kyoto, Osaka, and Nara. And if you haven't booked hotels yet, please proceed to do so.

Dec 29th night : Tokyo
Dec 30th afternoon : Head to Kyoto
Dec 30night/31/1 night: Kyoto
2-3-4 : Osaka/Nara/Kayosan (1 night each)
5: afternoon : head to Tokyo

Two issues.

The period from December 29 to January 3 is traditionally a very, very busy travel time in Japan because a lot of people go 'home' to visit family and friends. This year (2020), that will extend to January 5 (Sunday) because January 6 (Monday) is the first work day of the New Year so everybody and his mother will be travelling back January 3-4-5. You're going Tokyo-Kyoto on December 30 and back to Tokyo on January 5 - you probably couldn't pick two busier travel days if you tried.... Shinkansen tickets go on sale 1 month in advance and, for that time of year, reserved seats probably sell out almost immediately. You can obviously line up for non-reserved seats but a lot of other people are likely to be doing the same.

Secondly, for January 2-3-4, it appears that you're intending to move hotels from Kyoto to Osaka and then again to Nara? Absolutely no reason to do that - stay in Kyoto and just do a day trip to Osaka and to Nara.

Thank you all for the feedback. We've settled on the following itinerary

Dec 29 evening. Land at NRT and stay in Asakusa or Ginza area in Tokyo (suggestions?)
Dec 30th afternoon head to Kyoto (Understand it'd be busy :(
30/31/1/2: Park in Kyoto and see Kyoto. [lodging booked] (if we get done with Kyoto, we might do a day trip to Nara?)
3rd morning : Osaka and night in Osaka
4th morning : head to Koyasan and stay in Koyasan [lodging booked]
5th morning : head to Tokyo (via Kyoto I suppose)
5night to 7th evening : We will have 2 days and 2 nights to enjoy Tokyo. Shibuya is the area we are considering finding lodging in. Any advice?

Any further suggestions are welcome. Next we need to figure out transportation within. With this itinerary, do any passes make sense?

Thanks again for everyone's suggestions.

Another question. We are considering taking one backpack each (I have two teenagers) for the whole trip. I am thinking something that can hold 44L (like an Osprey Talon 44) or maybe even 36L would be sufficient. This way - we would be a lot more mobile. Anyone has done a backpack only travel with a similar itinerary?

Regarding your back pack question, I have done a two months cycling trip with a 31 L bag. It all depends on your ability to wash during your stay. Check with the hotels you have booked if you have access to a washing machine and dryer.

When using public transport, remember to put the backpack to the front, in order not to be a nuisance and danger to other users.

Enjoy your trip to Japan!