Itinerary around a Cycling the Nakosendo

Hi well travelled folks, I am planning to cycle the Nakasendo from Annaka to Kyoto over 7 days as part of a 30 day itinerary in September 2025.

I will be travelling with my wife who doesn't cycle and I am looking to have Kyoto as a meetup point.

Days 1-4: Tokyo (with my wife)
Day 5: Tokyo/Annaka
Day 6-14: Nakasendo Trail Arriving Kyoto
Day 15-17: Kyoto (meet up with wife)

I have about 14 days to play with post Kyoto with my wife and I will be departing ex-OSAKA (flexible) back to Australia. Looking for suggestions that would be cost/time effective train travel. Thoughts are:

Kinosaki
Hiroshima
Miyajima
Osaka - 2-3 days before departing

I was keen to take my wife on the Nakosendo trail Tsumago/Magome and possibly Kanazawa but I feel I would be back tracking, so looking more options on above; however I could work my way back towards Tokyo for departure and skip the places above.

Any suggestions welcomed.

I was keen to take my wife on the Nakosendo trail Tsumago/Magome and possibly Kanazawa but I feel I would be back tracking, so looking more options on above; however I could work my way back towards Tokyo for departure and skip the places above.

Maybe check out Yamanobe no michi between Nara and Sakurai?

Please note that currently (since many months) the road 18 between megane bridge and Karuizawa pass is closed. It might be reopened again next year. Google maps shows the road closure so you can check there. The alternative road has quite some traffic.

The other point you probably already know, in case you want to take public transport with your bicycle at some point, the bike needs to be in a bag. These bags are readily available in Japan. My personal recommendation is the one from Montbell , biggest size.

https://en.montbell.jp/products/goods/disp.php?product_id=1130426

Regarding what to do after Kyoto. Many options. There are many suggestions on JG.