Help with Itinerary... and JR pass?

Hello everyone,

Having done a good chunk of South East Asia, I'm now braving the wilds of Japan. Unfortunately I don't seem to have any colleagues who can give me good advice and such.... so am reaching out to you -

1) Would appreciate if you could critique my suggested itenerary

2) Would appreciate if you could provide some guidance around whether a rail pass makes sense or not.
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In Late September -

Week 1: Saturday - Arrive Tokyo from London
Sunday / Monday - Tokyo. See the usual stuff
Tuesday - Tokyo. Day trip to Nikko
Wednesday - Tokyo. Day trip to Kamakura
Thursday - Train to Hakone (Love Train???). Overnight in Hakone.
Friday - Hakone to Gifu OR Kanzawa. Overnight in one of the places.
Week 2: Saturday - Train from Gifu/Kanazawa to Kyoto
Sunday/Monday/Tuesday - Kyoto
Wednesday - Kyoto to Mt. Koya. Overnight in Monastary
Thursday - Mt. Koya to Himeji Castle (2hrs) and then on to Hiroshima. Overnight Hiroshima.
Friday - Hiroshima back to Tokyo. Overnight Tokyo (near airport).
Saturday - Fly back to LHR

Does this make sense from a do-ability standpoint (i.e., no ridiculous train journeys, too little/too much time in some places)? We're a fairly young couple and can easily stand a few rushed journeys.

Should I skip Kanazawa or Gifu, and stay an extra night in Hakone?

Does it make sense to get a rail pass or are one-off journeys better?

Any help you can provide would be much appreciated.

Cheers.

I would drop Kanazawa/Gifu and maybe add an extra day in Kyoto doing a day trip out to say Nara, Osaka or any other place in the region, or add an extra day from Hiroshima to visit Miyajima.

If you did get a RailPass I suggest you get a 7 day JR pass starting on the day you leave Hakone to wherever you might be going. Trips to Nikko, Kamakura, and Hakone can be done with specialized tickets or single fares.

Btw there are many ways to Hakone:

One of the trains is named "Romance Car" but it is just a name. Its not a car for just couples etc, everyone can ride in them.

There are also cheaper express trains that go there too.

If possible, I recommend to get an open-jaw ticket: enter Japan through Tokyo and leave through Osaka.