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Advice needed on passes and travel to naoshima

Hello!

I am heading to Japan with a friend in 2 weeks and we are very excited!

We have booked all of our accommodations but need to coordinate transportation. I am wondering if someone could help us understand the most efficient and cost effective way to travel? We are trying to figure out whether we should purchase a 7 or 14 day JR pass. Or just purchase individual train tickets?

Some other questions: Will the pass be helpful in traveling from the airport? I'm assuming we will also need to buy passes for local subway travel in each city (tokyo, kyoto, osaka)?

I've copied our itinerary below:

April 1-8 Tokyo (arrive in HND, staying in Shinjuku)
April 8-10 Naoshima *we would like to arrive in Naoshima around 3pm on the 8th.
April 10-13 Kyoto (we may do a couple day trips to shrines, and visit Nara from here)
April 13-16 Osaka (flight departs from KIX, staying near Namba)

Thank you in advance for your help!

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