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Will a JR Pass cover my plans whilst in Alps region?

Hi all

I am visiting Japan in May 2016 with my husband and 10 year old son for a family wedding in Osaka. After the wedding we hope to see some of the country by train and hope to include some time in the alps. I have reserved accommodation in Kanazawa for one night Wed 25th May and would then like to head into alps for two nights before travelling on to Hakone for the weekend.

However, I cannot decide where would be most appropriate for us to stay during our time in the alps.

My son says he would like to see the monkey park in Yamanouchi. I think we might also enjoy the castle in Matsumoto. Would we be best staying near the railway station in Nagano city itself and making day trips to these places? If so, will our JR Passes cover these trips?

I was planning on buying a 14 day JR Pass for each of us. Our full 15 night itinerary is:

18/5 Arrive Narita Airport. One night in Ginza, Tokyo

19/5-22/5 Three nights in Osaka

22/5-25/5 Three nights in Kyoto

25/5-26/5 One night in Kanazawa

26/5-28/5 Two nights in alps (?Nagano or Yamanouchi or Matsumoto?)

28/5-30/5 Two nights in Hakone

30/5-2/6 Three nights in Shiodome, Tokyo. Depart Narita Airport.

Not sure when to start using the JR Pass to make best use of it. Any thoughts?

Thank you for your help everybody! :-)
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