Tokyo-Fuji Five Lake-Takayama-Kyoto-Osaka

Hello SH-san!

Visiting Takayama is a great idea, it's one of my favorite places in Japan, the train ride there is also very scenic.

a.) I looked at normal ticket prices to see if a JR Pass would pay off:

Tokyo - Kawaguchiko ¥ 1,960, travel to Kawaguchiko station is covered up to Otsuki station, from here you have to take the Fujikyu line to Kawaguchiko (1,100Yen).
Kawaguchiko - Takayama ¥ 15,150 + (1,100yen from Kawaguchiko to Otsuki),
Takayama - Kyoto ¥ 9,680

This all adds up to ¥ 26,790 of rail travel which would be covered by the JR Pass. A 7 day JR Pass is ¥ 28,300, so right now it would be better to just buy tickets as you travel, however it may be come interesting to buy a JR Pass if you used it for additional travel, such as a day trip from Tokyo.

b.) Traveling from Kawaguchiko to Takayama can be quite the adventure. Kawaguchiko has it's own station and the full trip by rail takes about 500 minutes. This will pretty much take up a full day, so be sure to bring a good book. I would recommend taking the following route Kawaguchiko - Takayama. This would mean taking the train back to Tokyo station, where you can transfer to the Shinkansen to Nagoya. At Nagoya station take the Hida Wide View limited express to Takayama, this last part especially is very beautiful.

I hope this helps!
Daniel