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train travel in Japan

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Hi, We area family of 4, with 2 children age 19 and 23. We will be in Japan 12/20/14 til 1/3/15. Our itinerary is :
Hiroshima-1 night
Miyajima-2 nights
Kyoto -4 night
Tokyo 5 nights ( includes New years ,which I understand might make things a bit difficult)
several nights left ,considering Hakone,Nara
We plan to use the Japan rail pass during this time. I understand that several routes will be very popular and book up quickly. Can one make reservations ahead of time, or does one have to initiate the voucher and make the arrangements at tha time. I understand from the blog that many people have successfully done this on their own, but if I am having trouble, does anyone have a reputable in country tour agency that can help me navigate?
I sure appreciate your thoughts!

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