Hi Tenjin/Anybody : ),
Landing KIX/Osaka (2adults/2kids) Oct 8-> 2 days in Osaka (Local travel/Himeji castle) -> Kyoto for 5 days (Nara Day trip) -> Tokyo (5 days) (Day trip Hakone) -> Nagoya (Legoland) Oct 22 -> Back to Osaka/Oct 23 and out on Oct 24.
Advice/Comment please (could I do better?) : )
Comments
For Himeji, you could make it a half day trip with seeing the castle and Kokoen Garden nearby (get the combo ticket and save a little money) and then go see Kobe for half a day. Or you could make Himeji a full day by adding going up to Mt Shosha. Up to you.
https://goo.gl/65ZtRi
If you are also seeing Tokyo, you can mostly skip Osaka in the day. In the evening, the city comes alive and can be great - you can go there after a day of sightseeing in Tokyo. It's only 30 minutes away by train, and as long as you catch the last train back around midnight you'll be fine.
http://goo.gl/XE5R94
For Hakone, you can get a Hakone Free Pass at Odawara Station if you are touring the sights.
As for Tokyo, you could spend another day on a day trip if you like - there are many good places - Nikko, Karuizawa, Sendai, Chichibu, Kamakura & Enoshima, Yokohama, etc. Tokyo has a lot of good places, but for many, 3-4 days is enough.
https://goo.gl/qyQtGV
You can check on train info on Hyperdia - you can see regular fares, routes, and schedules.
http://www.hyperdia.com
Under "More Options", with a full JR pass, be sure to uncheck the Nozomi box since you can't ride that train using the pass.
Also, you can look at some previews of some of the best places to see in Japan on:
https://www.youtube.com/user/thejapanfaq/videos
There are also loads of other tips on
http://www.thejapanfaq.com/the-best-japan-travel-tips/
Best regards.
Thank you, Tenjin!