Early draft for late 2023 trip

Hello,

I’m in early planning phase for our holidays in Japan for late 2023. We have roughly 28 – 31 days available (we were travelling from South America so we definetly lose at least 2 days travelling to Japan) I divided the trip into blocks due to the proximity of one point to another. This is just the first draft so aside from Tokyo everything can be changed, added or rearrenged.

\- Block 1: Tokyo and daytrips (Kamakura, Nikko and Hakone)

\- Block 2: Matusmoto, Nakasendo (Magome to Nagiso), Nagoya

\- Block 3: Takayama, Shirakawa Go , Kanazawa

\- Block 4: Osaka, Kyoto, Nara, Mt Koya

\- Block 5: Himeji, Kinosaki Onsen, Hirochima, Miyajima

\- Block 6: Okinawa (Zamamijima)–> More details ahead

I will do this travel with my boyfriend. He saw some documentary where Zamamijima did some appareance and He is kind of obsesed with this island. The trip to Okinawa would be just to visit this island. It’s seems not to difficult to get to this island by ferry from Naha. Due to closeness, the flight to Naha will be propably from Fukuoka as it seems there is a lot of flights from this city. In my mind all this hassle to get to the island it’s not worth it at is time consuming and it means to use planes and ferrys who might be less reliable than trains (some questions about this below). So I’m not entirely sure to really add this to our trip.

Some additional information before questions :

1. We have been to Tokyo before but on a low budget so we visited a lot of free stuff in Tokyo. This time our idea is do more daytrips and some museums (neither of us went outside Tokyo in previous travel) rather than seeing the usual neighborhoods .
2. I did the math for 21 days Jr Pass and it’s seems to be worth it, so take this in consideration for question time.
3. Things we really like: food, hiking (nature) and photography.
4. In our past travel to other countries we discover that we like temples, but only the first ones. I suposse the temple fatigue is real, so I’m trying to not add so many temples to our itinerary unless they have some adding like a good hiking, good photography or good view.

Questions:

1. Our travel window is between mid-September to mid November. In past trips to other countries we have traveled on questionable dates due to climatic issues such as monsoon that had ruiner the trip so I learned my lesson and now I try to travel in better weather. Based on which I researched via internet, the peak season of typhoons ocure in august – september and doesnt affect that much to people travelling in those months. Which months during our period time for my draft do you recommend? My main concern is the Okinawa part as depends in ferrys and flights, also probably it will be the last part of our trip (to avoid overlapping with the active period of the JR PASS) so I’m a little affraid to lose some conecction to the final flight to home.
2. If I remove Okinawa, which place do you recommend me to add? Usually I like to stay in a place as a base for several days and do daytrips (in our trip this places will be Tokyo and Osaka) I was thinking if I remove Okinawa I will use Hiroshima as another base. Other option that I was thinking was adding Shikoku, in particular Iya Valley, as we like to drive to more remotes location.
3. It really worth it to accommodate the dates to observe and photograph momiji? Based on this year calendar, mid to late november seems to be the better month to see the autumn red leaf.

Sorry for the messy post, but it’s the initial draft. With your feedback I will choose a date and I will be able to better adjust the trip.