Help or suggestions for itinerary December Japan trip

I would drop Takayama. Trying to fit it in is going to eat up a lot of extra travel time, and involve looping around on slow transport through the mountains. Takayama is very touristy, and you'll have plenty of opportunities to sleep in a Ryokan elsewhere on your trip, if you like.

On this forum, we generally suggest spending a night in Nikko if you visit, rather than going as a day-trip. There's lots to see, and it's nice to be there in the early morning, before the daytrippers arrive en masse. You could also look into Kamakura as a day-trip out of Tokyo, perhaps combined with Yokohama in the evening. I personally think Kamakura is a much more interesting day-trip than Hakone, and it's also a lot cheaper! If the weather's clear, you can see Fuji from Kamakura.

Are you sure you need to visit Osaka? It's not that interesting of a city, and it's a bit of a mess. A smaller, much less interesting version of Tokyo. Unless there's something specific you want to see/do there, your time is better spent elsewhere in Kansai, in my opinion. Koyasan is really cool, though temple accommodation there is expensive.

If you like castles, look into Hikone, which you'll be passing through anyway on your way between Kanazawa/Takayama and Kyoto.

I don't think you need a JR Pass. Travel on local trains and buses will be much cheaper. Hakuba to Kanazawa might be a little complicated, unless they have direct buses. I've never been to Hakuba.

Its all possible,it really just comes down to personal preference.

I agree with giora on the JR pass.Not necessary for that itinerary,just take local trains,buses etc.

One thing I'd look at would be flying on from Kansai,instead of heading back to Tokyo.If possible that would save you backtracking(time and money).

On the specific,and based on MY interests...no idea on the skiing part,but apart from that.

I'd also have an overnight in Nikko.I'd keep Hakone which I like a lot.

If you want to see Koyasan then I'd sleep there one night.I'd cut Osaka,unless there is something particular you want to do there? And you have a great castle in Matsumoto,so on your timeframe I'd probably also cut Himeji.

I agree that the J Alps part is too fast,too much time in transit for the number of days.So you could add time there,or cut something.

I'm ok with Hakone, but I wouldnt do it at the end of my first stay in Tokyo, right before heading to Matsumoto. You dont save anything by trying to catch onward travel from Hakone, so why not have 1-2 days in Tokyo, then Hakone, then 1-2 days in Tokyo, then Matsumoto and onward.

I agree Nikko is better as an overnight. It takes a while to get to and from, and the days are very short in December.

I also agree that Osaka probably isnt worth your time. You could find more to do in additional days in Tokyo or somewhere else. If you really want to see it, you can easy add it as a day trip from Kyoto.

And yes the JR pass is not going to save you money, it usually doesnt. Individual train tickets and the option to take buses will be much cheaper.

Takayama is fine, although it does slow you down. But it can be an excuse to see the villages of Shirakawago. Need not 2 nights though, it is rather small. Kanazawa could be 3 nights if you like.

I like the idea to buy train tickets as you need them. I also recommend spending some time in Kyoto. See the amazing temples. What I do is stay in Osaka by the train station and take the train into Kyoto for day trips plus do day trips to Nara.

I like the idea to buy train tickets as you need them. I also recommend spending some time in Kyoto. See the amazing temples. What I do is stay in Osaka by the train station and take the train into Kyoto for day trips plus do day trips to Nara.

Staying in Kyoto and doing Osaka as a day trip tends to be better than staying in Osaka and trying to do Kyoto as day trips.

For one there is just so much more to see in Kyoto.
Secondly Kyoto's sights tend to be far from the central train stations.
All that time on the train also adds up in cost and time.

So staying in Osaka to see Kyoto, days end up looking like:
Get up, eat breakfast, take the Osaka subway to the right train station, train to Kyoto, Kyoto subway or bus to area of Kyoto where the sights are, walking to the actual sights(it's getting late in the morning by the time you arrive). Limited time at morning site, lunch, relocation to the afternoon area, afternoon sight potentially in the heat or rain, then kyoto bus or subway back to the train station, then train to Osaka, then possibly Osaka subway, followed by exhaustion.

No point at all for me.Quite apart from the time wasted.

If its a financial decision,there are plenty of reasonably priced hostels in Kyoto.Plus...without a railpass,adding the price of a train to and from Osaka every day....

This is a very belated response - apologies to all who took the time to reply, I assure you I appreciate all the advice.

We have made a few small changes to the itinerary. Namely, we are now flying out from Kansai international on the 26th of December, and we have added an overnight stop at Magome to do the walk to Tsumago. I understand the weather may be hit and miss at that time of year, but even if it is impassable (unlikely from what I've read) it still looks to be a pleasant enough place for a night. We have also taken on board some of the advice and will likely be dropping Himeji given that we will be visiting the castle in Matsumoto and possibly Hikone. We'll be cutting Takayama down to one night, but will still be going to Osaka - a bit of a gamble maybe but we've now arranged to meet some travel buddies in a hostel there for Christmas so time will tell what we think of it as a city.

I should have also clarified that where I have listed a date and a location, I meant that to mean we will be spending the night of that date in that place.

New itinerary

5 nights Tokyo
2 nights Matsumoto
2 nights Hakuba (skiing)
3 nights Kanazawa
1 night Takayama
1 night Gifu
1 night Magome
1 night Hikone
5 nights Kyoto
3 nights Osaka
Then fly to Bangkok!

I think I might either get rid of the overnight stay in Gifu or Hikone, OR cut 1 night from Osaka to add an extra night in Kyoto. I might also stay in Matsumoto just the one night, using that extra time to have an overnight stop in Nikko from Tokyo.