I need advice on which Regional Pass should I buy with my Itinerary ?

Hi there,

Yaeyama, that's amazing! Is your flight to Ishigaki? If you're flighing JAL, this is the longest domestic first class flight. Well worth to check if you can upgrade on the day of travel.

After, you will be spending a good amount of time in Kyushu but places like Kurokawa Onsen can only be reached by car/bus, so a JR Pass does not make sense here.

From there it is all a one way to Tokyo, and there too buying normal tickets makes the most sense.

Kind regards,
Daniel