Japan October Accomodation Help/suggestions

[ketsuzei]

I would skip Osaka, mix Hakone somewhere into your Tokyo stay, and then go Tokyo-Kanazawa-Kyoto-Nagasaki by train and fly back to Haneda to pick up your flight home. Do Osaka and Kobe as day trips from Kyoto if they really appeal. A lot of the temples in Kyoto are best first thing in the morning (both in terms of atmosphere and tourist numbers), which leaves plenty of time to go elsewhere.

 

[trixydoza]

I second the Kanazawa (+ Wajima) and Nagasaki suggestions. But I'd suggest not planning a full day after the Nagasaki Peace Park, the experience left me utterly exhausted.

The Japan Rail Pass is of course a great buy, but the JAL and ANA fares for visitors also warrant attention:

Visit JAPAN Fare?ANA
https://www.jal.co.jp/yokosojapan/

And Okinawa is worth working into an itinerary if you find that flying leaves you with more time.

Finally, this is a stunning place to stay, again only if you can work it in somewhere:

Ryokan Yoyokaku-Information

20 days is enough to have a brilliant time, and the weather should be great (hopefully typhoons stay away).