>>1423685That route is pretty sweet. It took us 11 days to make it from Outside of Odawara to get to Kyoto and we were going slow. There was also a two day stop because of Typhoon Hagabis.Just make sure you go up Hakone!
So you could probably make it it, but you are right. The thing that sucks about the tour is you don't get much time to do anything outside of bicycling. Everything is random encounters. Some days I envied backpackers because to switch from bike to bus to train to hiking seems much easier when the country is so crammed and public transportation is so readily available.