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Takayama will also be very cold in December. Overnight low is typically below zero, day time high in single digits. GP

I actually prefer to stay in Osaka. Kyoto is good for sightseeing by day, but I think Osaka is a more interesting city at night, and I'd sooner a quick return to my hotel from wherever I am late at night. I have stayed in Kyoto, and been there at night, but I prefer Osaka overall. Cheaper...

I think Okayama is a great base for that area. It also gives access to Shikoku, although I wouldn't bother going there on a first 9-day trip. However, if seeing castles was a high priority, Matsuyama castle is good too and I think can be done as a long day trip from Okayama. Or stay there the...

Get the one-week rail pass, base yourself in just two or three places (less accommodation to book and less travelling with luggage) then day-trip to the sights. Note that rail passes cannot be used on the Nozomi shinkansen. Try to get the Hikari Rail Star, as the Kodama ones stop at lots more...