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Japan trip

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Hi, I am visiting Japan in October with my mum and would be really grateful of any help that I can get with my itinerary.

Here's my thoughts...
Arrive Haneda Saturday stay in Tokyo for 3 nights.
Travel early to Kyoto and stay 2 nights (Tues/Wed)
Leave Kyoto early and stop at Hakone for 1 night (Thurs)
Return Tokyo Friday evening after day in Hakone
Depart Haneda on Sunday

All sounds ok in theory! But I am looking for advice about place to stay, travelling, JR pass etc.

I am also struggling with the stop off at Hakone.... Is it worthwhile? I think I would like to experience ryokan/onsen. But seems difficult with baggage.

Any advice would be so appreciated.
Thanks.

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