3 week itinerary - is this doable and what passes make the most sense?

Here is a sequence suggestion :

Osaka
Kyoto
Tokyo
Hakone
Side trips to Takayama (2nights)
Shirakawa-go (1 night)
Kanazawa
Matsumoto
Back to Tokyo

Hello there,

Assuming you would want to go into the Alps right after Kyoto, my advise would be to travel to Kanazawa, from there go to Takayama, or alternatively swing by Shirakawag by bus. From Takayama/Shirakawago buses travel to Guji Hachiman.From there is would make most sense to travel to Nagoya and take a train from there to Matsumoto but fore going to Hakone and Tokyo.

Please be aware that you'll spend a good amount of traveling and I would advise a minimum of 8 days for this part.
For this itinerary it would be better to buy normal tickets, you could also look at a Hokuriku Pass.

Hope this helps,
Daniel

Daniel, michvoo, Thank you for your answers.

Assuming that I do want to go from Kyoto to the Alps and end that portion of our trip in Hakone, besides Kanazawa and Takayama, what other places do you recommend visiting? I'm not tied to Guji Hachiman, especially since it seems complicated to get there. We do have about 7-8 days to spend in this region.

Please advise!

Thank you in advance.

Hi again!

Well there is much more you could visit. Gero-Onsen (onsen town near Takayama), Kamikochi, the Kurobe Alpine route and my previously mentioned Shirakawago all come to mind and make for very nice visits. Alternatively you could spend a day in Nagoya between traveling from Takayama to Matsumoto.

Kamikochi is easy to visit from Matsumoto by bus and is easy to fit in as a day trip.

There's a lot to explore and visit!