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Tokyo 3 nights
Takayama 2 nights
Matsumoto 1 night
Tsumago 2 nights
Kyoto 4 nights with a day trip to Nara
Kinosake Onsen for 2 nights
Travel back to Tokyo with a stop in Osaka
Tokyo 2 nights
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Wow sounds like you have a really great trip lined up. Takayama and Matsumoto are amazing places. I believe Takayama's claim to fame are their pickled veggies, which the Ryokan we stayed at, gave us a very nice sampling.
We missed Nara our last time around, but this time we plan on getting there, and if you are into Aquariums, the Osaka Aquarium is one of the biggest in the world.
Another good piece of advice I found helpful was luggage forwarding, this was a huge help since we were able to forward our bags to the next hotel without having to lug everything around.
Hope you have lots of fun!