Yet another 2-week Japan itinerary help (high level)
 

Japan is so rich in what it has to offer, I don't think I have ever had more challenging task planning a trip. Everything I read on this forum thus far is absolutely indispensable and for that I am really grateful to all who contributed.

I am a bit stuck and need help in mapping the route of our 2-week itinerary (Nov.12-26).

1) We land to Haneda at 5PM on Nov. 12th, plan to stay in Tokyo for 4 nights
2) On Nov. 16th we are heading to Kyoto for another 4 nights
3) On Nov. 20th we would like to move on but this is where I'm stuck: we want to see Hiroshima and Naoshima (both are a a must) and the rest is swirling me in circles. Should we make Okayama our base and then from there make day trips to Hiroshima, Naoshima and other places or do we split the remaining 6 nights between Okayama and wherever else (or skip Okayama altogether)?
Additional dilemmas:
1. Should we extend our stay in Kyoto for at least 1 night in order to make a day trip to Nara?
2. Should we visit Himeji castle on our way West (to Okayama or wherever else we decide to spend those 5-6 nights)?
3. Are we missing out by not going to Osaka?
4. What else is there between Kyoto and Hiroshima that I'm not thinking about (of course, there are a lot of things/places - that's why it's so challenging to plan a trip)
5. Our return flight from Haneda is on Nov. 26th at 6:50PM - should we return straight to the airport from wherever we happen to be at the end of our trip or back to Tokyo for one more night before leaving?

I guess my main concern is that I'm trying to jam too much into a short period of time. We are in our 50s, and as active as we are we also enjoy taking it easy. :) We love to walk a lot, enjoy art and architecture, nature and food (very broad terms, I know) and people watching. We are there in high season for autumn colors and will appreciate that too. One of us had been to Tokyo before but this is our first Japan trip together (and outside of Tokyo). I feel conflicted, trying to plan a nice, enjoyable trip and how to estimate if what I'm planning is going to be too stressful and arduous. I know that's very personal, but any experience based insight will likely be very helpful. Any thoughts on this, itinerary suggestions - I'd really appreciate it.

Thank you!

1. You could do that. Nara is definitely worth the day trip or overnight.
2. Himeji-jo is a gem. You can use takkyubin to lighten your load.
3. Maybe. If you don't know what you are missing then you won't miss it.
4. Yes. You could consider 2 or 3 nights for Hiroshima/Miyajima
5. You have lots of options. You could fly to Haneda from anywhere in Japan.

>> how to estimate if what I'm planning is going to be too stressful and arduous.
Pressure is external. Stress is internal and is usually a response to pressure. When I feel stressed I (try to) remember that I am causing it, not the pressure. Traveling in Japan is pretty easy as long as you can cope with crowds and be patient.

What is it that you think would be stressful or arduous? I don't understand what would be arduous to you.

On the 15th you want to go to Meiji Jingu for Shichi-Go-San.

2. Himeji-jo is a gem. You can use takkyubin to lighten your load.
3. Maybe. If you don't know what you are missing then you won't miss it. - True. I was thinking after I had posted this how it's a pretty superficial question. Your response is fair. I guess what I really meant to ask is in the context of what I listed as preferences, would Osaka significantly enrich our experience?
4. Yes. You could consider 2 or 3 nights for Hiroshima/Miyajima - As addition to or a replacement to making Okayama a base?
5. You have lots of options. You could fly to Haneda from anywhere in Japan.

>> how to estimate if what I'm planning is going to be too stressful and arduous.
Pressure is external. Stress is internal and is usually a response to pressure. When I feel stressed I (try to) remember that I am causing it, not the pressure. Traveling in Japan is pretty easy as long as you can cope with crowds and be patient. - Wise suggestion regarding the perception of stress.

What is it that you think would be stressful or arduous? I don't understand what would be arduous to you. - Moving on from place to place so quickly. Again, I understand that it's a personal preference but sometimes others share their thoughts on how they experienced it that helps you clear up your own mind on the subject.
Thank you, mrwunrfl!

>> Moving on from place to place so quickly.

I thought that might be it. Osaka can be visited easily from Kyoto. Himeji can be visited from Kyoto or Okayama.

>> in the context of what I listed as preferences
Yeah, the context was "art and architecture, nature and food". There is a saying that Kyoto people love fashion and Osaka people love food. I really like Osaka-style okonomiyaki more than Hiroshima-style. Takoyaki is a thing in Osaka. Osaka-jo is impressive, even if it is a reconstruction, and the original one played an important role in Japanese history.

>> As addition to or a replacement to making Okayama a base?
I was suggesting that Hiroshima and Miyajima deserve more than a day trip. That is, it would be worth the move from Okayama (to me).

You could keep Okayama as a base. You would spend a day (or more) seeing Okayama and Kurashiki. Vitsit Naoshima and Himeji from there. The Seto Ohashi bridge system is just east of there. It is a pretty awesome ride over the Seto Nai Kai to Shikoku. I would go to Kojima (denim capital of Japan!) to view the bridges.