Is it worth it to buy the JR pass for our 15-day trip?

Hello!

My partner and I are traveling to Japan in late March for 15 days. We are planning on doing the following travels:

* day trip from Tokyo to Kamakura and Yokohama
* Tokyo to Kanazawa
* Kanazawa to Takayama
* Takayama to Kyoto
* day trip from Kyoto to Nara
* Kyoto to Osaka
* day trip from Osaka to Hiroshima
* Osaka to Hakone
* Hakone to Tokyo

We used the calculator and the 14-day pass was estimated to be $65 more per person than individual tickets. Is it worth it to spend the $65 for peace of mind, seat reservations, etc? Open to any suggestions!

Also, if we were to buy individual tickets, is it easy enough to buy them once we are there, or is there a way to buy them in advance?

TIA

by ThePerfectNectarine

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