we have a trip planned for our family of 4 (2 of us are arriving in Haneda and 2 in Narita) on Sat. We will spend the first 6 nites in Tokyo (traveling for 1 day to Nikko,and possibly 1 day to Kamakura and/or Yokohama, then 2 nites in Hakone, 1 nite in Kanazawa and 4 nites in Kyoto with an evening in Osaka (not an overnite) , then back to Tokyo for one final night. I am sure a 7 day pass is worth our while but not sure about the 14 day pass. If it is the same (not more), I would purchase if it makes the travel easier. I also wonder if you recommend side trip to Kamakura or Yokohama. Also to Nara from Kyoto. Thank you.
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You would of course get a lot better value if you completed all your long distance travel within 7 days. There are other regional passes you can use for the side trips like:
Tobu Nikko Free Pass:
https://www.japan-guide.com/e/e2358_002.html
Enoshima-Kamakura Free Pass:
https://www.japan-guide.com/e/e2358_003.html
Hakone Free Pass:
https://www.japan-guide.com/e/e2358_008.html
http://www.japan-guide.com/e/e5210.html
Seeing Nara from Kyoto is highly recommended - it has some of Japan's best sights. Most of the best is in the Nara Park area. Kamamura is nice as well, plus Enoshima. Yokohama has its gems as well, such as the Sankeien Garden. For Tokyo, 3-4 days is enough for most people.
Since you are already seeing Tokyo, you can largely skip Osaka during the day. After the temples of Kyoto close down around 5PM, you can zip over to Osaka for the evening. At night the city comes alive and has some great places to see, such as Dotonbori, plus the night views from the Umeda Sky Bldg and Abeno Harukas Bldg are wonderful.
On another evening, you could also go and see Kobe.
You can see regular fares, routes and schedules on Hyperdia.
http://www.hyperdia.com
Under "More Options", be sure to uncheck the Nozomi box since you can't ride that train using the full JR pass.
You can see previews of some of the best places to see in Japan on:
https://www.youtube.com/user/thejapanfaq/videos
Hope that helps.