Best route - and what to add

Hello Rhys,

It feels like a bit much but I do think that you can do it. I would do it in the following order Tokyo - Nagano (for Show Monkeys) - Matsumoto (and trip from there to Kamikochi) - Kyoto (&side trips) and then return to Tokyo. I think you should take a minimum of 6 days for all of the above, however you could use the 7th day of the JR Pass to visit something extra. For instance how about a visit to Hiroshima or Nikko?

Either way, you are making great use of your JR Pass.

Happy travels!
Daniel