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Fly into Osaka instead of Tokyo for Koyosan to Nikko trip?

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Our first trip to Japan. We have two weeks. Not staying in Tokyo this trip. Going in April 2015; interested in historical sites/shrines, gardens, traditional towns, some hiking, a few more rural areas. We'd like to stay in at least one ryokan, plus a temple stay at Koyosan.

Thinking we might fly into Osaka and out of Tokyo (or should we do the reverse?). My first pass at an itinerary is:

Koyosan - 1 night
Nara - 1 night
Kyoto - 5 nights
Takayama - 3 nights
Hakone - 2 nights
Nikko - 2 nights
Tokyo- overnight near airport prior to departure

Does this sound about right? How should we sequence the places we'd like to stay? If we fly into Osaka, where should we start? I wish we could figure out a loop, but it seems like we have to do some backtracking. I haven't checked how the trains run yet (it might be easier to get to Koyosan from Kyoto than Nara? not sure)

I haven't made any reservations, air or accommodations, yet. Hoping to get some advice first. Am sure I will have many more questions once we get these basics down,

Are we missing something/ Jumping around too much?

Thanks so you Japan experts!

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