This travel itinerary is un-travelled. This is a preparation work done a couple of years back to visit Shikoku island in Japan.
What you need is 10 days ( 2 week-end and 1 week holiday), it's better departing from a neighboring country on a Friday evening after work if work schedule allows it.
Shikoku intrigued me because of the 100 temple pilgrimage or Shikoku Junrei with its 88 official temples and 20 unofficials. There seem to be a lot of hiking trails and beautiful landscape as well as mystical temples to see. Apparently part of the island has some good bicycle lanes as well for the ones having more time and willing to do this island with a more sport focus orientation.
At first I caressed the idea of hiking a very small part of the pilgrimage route, but gave up since some seemed to be very hard hikes and I am really not fit.
This is a itinerary departing and leaving from Osaka. I think that once you have already done the main sites (Kyoto, Tokyo etc...), Japan has much more to offer and this is one trip I will do for sure this travel itinerary to Japan someday soon.