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Belagerent
Alan_tbt
Did a similar route but went onwards through Osaka to Hiroshima. Took us 2 weeks with a 3 day break in the middle as my girlfriend had a bad knee. Neither of us were particularly fit and managed it fine (caveat, she's Japanese so all i had to do was motivate her and block the wind).
Definitely do cardboard box instead of travel case. We had squishy Evoc's and planned on putting them in there amazing airport postal service but they were a few cm's out and we had to struggle into Tokyo to loose them. Use paper packing tape as they're rightly finnicky about recycling and you'll spend hours unsticking plastic tape.
Not sure where we're at in terms of roaming charges these days but you can get a portable wifi hub in the airport to take with you. Can't remember if we ordered it to be collected it there or it was an in house service but i can check if you want me to.
There'll be times you'll need/want to use the train. Your bike needs to be in a bag for this. We had two lightweight covers that packed down to tennis ball size that did the job perfectly. If i can find ours you're welcome to borrow them. You might want to think about getting the train/shuttle to Yokohama when you arrive to avoid the worst of the traffic.
In land the hills can be massive and take a really long time. Coming back down is a lot of fun but be mindful of how fast you can go coming back down. We headed to the coast to avoid some of the hills and occasionally got battered by the winds so again took a lot of time.
We mostly stayed in hostels and i'd say the only downside to our trip was having to always reach our destination in time. That meant some long days in the saddle where we had to push on and missed out on hanging out with the people we met along the way (although i did manage to have dinner with a skateboarding monk who let me hit his big bell...). If we ever did it again we'd plan on staying where ever we could find each night but appreciate that's more easily done with a native speaker.