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Japan Itinerary and Train Help

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I am taking a multi-country trip in Asia that I am about to book using miles. Basically, i have a choice of spending four days in Kyoto, where I have been once and loved; or, I can spend 8 days in Japan, flying in and out of Osaka.

If I spend 8 days, I was thinking about Kyoto for four days, then Tokyo for three days (where have been, but did not love; but i'm willing to give it another chance), and one night in Osaka before departing. the idea would be to take Shinkansen trains between the cities. But I am struggling a little with the expense and travel time of going to Tokyo after not having had a great time there before; on the other hand, I feel like if I am in Japan, and I have the time, I really should revisit it and give it another chance.

Does this sound like a good itinerary? Would it make sense to buy a JR pass? I think I would want a Green car (1st Class) pass due to traveling with a large bag, which seems to be about $500 for 7 days. Is there a better way/ more economical way to do this? Is there a different 8 day itinerary that would be suggested?

Also, if my Tokyo my last stop, is there a direct Shinkansen that goes from Tokyo to Kansai airport early enough in the morning to make an 11 am flight?

Thank you for the help!

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