Will 14 day JRPass cover my itinerary? Best train to catch? What line?

Hi Vicky,

The JR Pass is best used for longer trips, hence it makes sense to start using it once you depart from Tokyo.

For travel to Naoshima, the best route from Hiroshima is to take the Shinkansen to Okayama station, then a local train to Uno station. From there you can get on the ferry to Naoshima.

Between Naoshima and Kyoto? You could stop at Himeji, the castle and garden is very beautiful and great for a couple hour stopover. Kobe is also very interesting and has many small places worth a visit. Then on the way from Kyoto to Odawara, there are not really many easy stops or that are right in the middle. However a visit to Hikone (not Hakone) is a nice historic town to see and visit. Nagoya is about in the middle but it is very much a business city and not so much for tourism.

Hope this helps,
Daniel