Such a great place, was a nightmare to plan though as wanted to go everywhere. Will certainly be going back as so much more to see, went with
5 nights Tokyo
3 nights Takayama
5 nights Osaka
5 nights Koyoto
3 nights Tokyo
They were mainly bases, with the rail pass did lots of day trips out so didn’t actually spend all that time in Tokyo as went to Yokohoma, Kobe, Hakone, Nikko etc. also picked up a car to explore more rural areas in Takayama. Some of the stand highlights were spending a day at Miyajima island and walking up Mt Misen for the views and taking the last ferry home with deer just wandering about the terminal. As mentioned above Enoshima is lovely and easy to get to from Kamakura, so peaceful sitting watching the sunset over the coast.
Had no really issues with language, had a pocket wifi to help with any translation but plenty of English about. At Nara had multiple children from school trips come and ask questions and to sign their books and their English was amazing, they also gave origami gifts for taking part. Even in Takayama got by fine when going to local bars and restaurants, so friendly as well drank the one out of a brand of beer so the next round was free…
On the money front certainly recommend a card like Monzo or Starling as everything was cash heavy and the ATMs could be weird. Was certainly odd going to gigs out there, Why? were touring out there when I visited and just emailed the promoter and they reserve a ticket that you pay with cash when you arrive.