From Shibu Onsen to Shirakawago

Hi
I'm planning a 10 day trip to Japan starting from Tokyo and ending in Osaka
I wish to know what is the best way to travel from Tokyo-Shibu Onsen (Jidokudani Monkey Park, overnight)-Shirakawa go (Overnight)-Kyoto
Can someone advise me the transportation and timing needed to travel?

itinerary:
Day 1-3: Tokyo
Day 4: Yudanaka - Shibu Onsen
Day 5: Jidokudani - Shirakawa go
Day 6 - 7: Kyoto
Day 8-10: Osaka

Many thanks in advanced!

I recommend:

Tokyo - (shinkansen) - Nagano - (Nagaden Railway) - Yudanaka - (bus or pick-up service) - Shibu Onsen

Shibu Onsen - (bus or drop-off service) - Yudanaka - (Nagaden Railway) - Nagano - (Japan Railways) - Matsumoto - (bus) - Takayama - (bus) - Shirakawago

Alternatively, you could travel from Nagano along the Sea of Japan coast:

Nagano - (Japan Railways via Naoetsu) - Kanazawa - (bus) - Shirakawago

Train timetable:
http://www.hyperdia.com/

Matsumoto-Takayama bus:
http://www.nouhibus.co.jp/english/matsumoto.html

Shirakawago bus:
http://www.japan-guide.com/bus/shirakawago.html

Tks! That's super helpful! Guess I have to start planning the routes! Cheers !

- By the way, currently i have a rough itinerary, hopefully you can help me suggest if it's too rush especially day 7 & day 10? Or if there's anything i can squeeze in?
I'm taking into account winter sunset ends at about 4.30-5pm so trying to wrap up sightseeing within that period.
- Also i'm NOT intending to get a JR pass because most of my travels will include both JR and non JR lines which after calculating doesn't seem worth it. What do you think?

Day 1-3: Tokyo: haven't really planned, but Tsukiji market, sensoji temple, Shinjuku and disneyland are top of the list

Day 4: Shibu Onsen, Jidokudani Monkey Park

Day 5: reach Takayama by 2pm+

Day 6: reach Shirakawago by 2pm

Day 7: Kyoto by 3pm
- Shijo Dori (shopping & dinner)

Day 8: Kyoto: Kiyomizudera, ninen zaka, sannen zaka, lunch @ Gion, Kinkakujji, dinner & shopping @ Kyoto Stn

Day 9: Kyoto: Fushimi Inari Shrine, Arashiyama, dinner @ Pontocho (anything else i can squeeze in here? or spend time in arashiyama)

Day 10: Travel to Nara (Todaiji Temple, Nara Deer Park, Kusaga grand shrine), Shinsaibaishi/America Mura, Hozenji Alley, Namba, Dotonburi - then travel back to Kyoto hotel (Is this feasible?)

Day 11: Travel from Kyoto to Osaka Kansai Airport