itinerary with jr pass

Daniel. We are arriving at Henada Tokyo on evening of 6/23 and have booked a place until 6/25. From Tokyo we are going to Kyoto from 5/25 leaving 5/28. Then on to Kyosan from 5/28 to 5/29 Then to Nara from 5/29 to 5/31 We leave for Naoshima Island on 5/31 and plan on staying for two days leaving on 6/2 back to Tokyo. We leave Japan on 6/4

Are most if not all trips covered by JR Pass, and do we need a 14 day pass not a 7?

We may switch the trip around to go to Kanasara from Tokyo and then move Kyoto bak to the end of the trip.

Any suggestions.
THX
John