Hello!
Brief check made us unsure whether we need the JR pass or not and if so, how long (14 or 21 days). Some advice would be welcome!
Our schedule:
Day 1: Arrival in Kansai Airport - 1 night in Osaka
Day 2: From Osaka to Koyasan
Day 3: From Koyasan to Kyoto with a trip to Nara on the way
Day 4 - 5: Kyoto
Day 6: From Kyoto to Matsumoto
Day 7: From Matsumoto to Nagiso
Day 8: Bus to Magome (we stay two nights in Nagiso)
Day 9: Train and bus to Hakone (we stay at Moto Hakone and will use ferry / local bus)
Day 10: From Hakone to Shirahama
Day 11: Day trip somewhere on Izu peninsula
Day12: From Shirahama to Nikko
Day 13: From Nikko to Tokyo
Day 14 - 17: Tokyo (local transport + for ex. Kamakura)
Day 18: Tokyo to the airport :(
Thanks for the feedback!