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Japan Itinerary for May

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I am planning on going to Japan for ~3 weeks in May. Leaving Canada on the 6th and arriving in Osaka on the 7th. I have quite a bit planned out but thought I would see what some people who have been to Japan have to say.

Simplified Itinerary:
May 6th: From Regina to Vancouver to Tokyo (overnight)
May 7th: From Tokyo to Osaka
May 8, 9,10: 3 Full days in Osaka (possible day trip, see below)
May 11th: Head to Mt. Konya and stay overnight (only for sure thing as I managed to get a reservation at a good temple)
May 12th: Depart Konyasan for Kyoto
May 13, 14, 15, 16: 4 Full days in Kyoto (although I am pretty sure I will head for Nara one of the four)
May 18th: Depart Kyoto for Tokyo
May 19, 20, 21, 22 ,23, 24, 25 ,26: 8 Full days in Tokyo (and area)
May 27th: Tokyo to Canada

I was thinking of extending my stay in Kyoto and take 2 days from Tokyo. That way I can see more while doing some day trips. I want to go to Iga Ueno so it is likely I will take a day out of tokyo and stay in Kyoto longer. I know a lot of people say Tokyo isn't too spectacular for a long stay but I did a euro trip two years ago and don't know if I want the whirlwind tour again :).

Big question is if I should do a day trip for Osaka to Hiroshima. I plan on returning to Southwest Japan in the future (who knows when exactly) and am not too concerned about all the sites out that way but I do feel I should get to see Hiroshima just in case.

I am going to get a JR Pass.

I am open to suggestions :)

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