Advice on Traveling Kyoto, Osaka, Nara and Naoshima

Hello!

We are traveling to Japan in March (please see itinerary below). We plan to purchase a 7 day Japan Rail Pass and activate it on Day 5 to travel to Kyoto. From there we will take day trips to Osaka and Nara, and then finally visit Naoshima before returning back to Tokyo.

Can we use the JR Pass for all of these destinations (outside of Tokyo)?
Do you see any complications with this itinerary?

Day 1 - March 19 (Thursday) - Arrive in Tokyo
Day 2 - March 20 (Friday) - Tokyo
Day 3 - March 21 (Saturday) - Tokyo
Day 4- March 22 (Sunday) - Tokyo
Day 5 - March 23 (Monday) - Leave for Kyoto (activate pass)
Day 6 - March 24 (Tuesday) - Kyoto
Day 7 - March 25 (Wednesday) - Day Trip to Nara
Day 8 - March 26 (Thursday) - Day Trip to Osaka
Day 9 - March 27 (Friday) - Leave for Naoshima
Day 10 - March 28 (Saturday) - Naoshima
Day 11 - March 29 (Sunday) - Leave for Tokyo
Day 12 - March 30 (Monday) - Tokyo
Day 13 - March 31 (Tuesday) - Leave for States

Thank you for your help!
Scott