Japan 3 weeks itinerary

Hi People,

I'll be doing a solo 3 weeks backpacking trip through the Kansai region and Tokyo coming Nov-Dec. Some comments on whether the following itinerary is doable or areas to improve on will be really helpful.

Fri: 20Nov2015: Touchdown Osaka 10pm
Sat: 21Nov2015: Osaka sightseeing
Sun: 22Nov2015: Osaka sightseeing
Mon: 23Nov2015: Osaka sightseeing
Tue: 24Nov2015: Morning travel from Osaka to Koya San, one night temple stay
Wed: 25Nov2015: Afternoon travel from Koya San to Okayama, one night stay at Okayama
Thu: 26Nov2015: Afternoon travel from Okayama to Naoshima
Fri: 27Nov2015: Naoshima sightseeing
Sat: 28Nov2015: Afternoon travel to Hiroshima
Sun: 29Nov2015: Hiroshima day trip to Okunoshima
Mon: 30Nov2015: Hiroshima day trip to Miyajima
Tue: 01Dec2015: Afternoon travel from Hiroshima to Kyoto
Wed: 02Dec2015: Kyoto sightseeing
Thu: 03Dec2015: Kyoto day trip to Nara
Fri: 04Dec2015: Kyoto sightseeing
Sat: 05Dec2015: Kyoto sightseeing
Sun: 06Dec2015: Morning travel from Kyoto to Kanazawa, one night stay at Kanazawa
Mon: 07Dec2015: Afternoon travel to Takayama, one night stay at Takayama
Tue: 08Dec2015: From Takayama, take a tour bus to Shirakawa Go and Gokoyama, return to Takayama and travel to Tokyo
Wed: 09Dec2015: Tokyo sightseeing
Thu: 10Dec2015: Tokyo day trip to Hakone
Fri: 11Dec2015: Tokyo day trip to Mt Fuji
Sat: 12Dec2015: Tokyo day trip to Nikko
Sun: 13Dec2015: Tokyo sightseeing
Mon: 14Dec2015: Evening flight back home.

I have a couple of worries regarding the above itinerary
1: Is it too fast/pack to enjoy each location?
2: Is the 21 days JR pass required?
3: Will there be any issue with connecting to the trains and ferries (will do further research on this as well)?
3: Are thicker clothes required (would really like to travel light)?

Would really appreciate any guidance/help here.

Thanks so much!

Sam.

1. I would say you travel speed is mostly slow and medium pace. Is this the pace you like to travel at? If so, then its all good.
I would say you have enough time to throw in Himeji, Kobe, and an onsen town and still have time left over.

2. Nope, the pass is not required. Purchasing individual tickets is more cost worthy.

3. What issues? Miyajima ferry is a frequent and stops after sunset.
Okunoshima has about 6 or 7 a day with intervals up to about two hours.

4. For myself, I seldom use thicker clothes. If need be I would pile up the number of layers. But usually in November, two layers is sufficient unless you are going to a mountain. E.g. Shirakawago or Mount Rokko

Note: What do you mean by day trip to Fuji from Tokyo. Aren't you already heading to Hakone? Might as well do a Tokyo-Hakone-Fuji-Tokyo.