So our general plan is some combination of:
Disney for three days near the start (to avoid New Years)
Tokyo for 3-4 days (I want to do Shibuya and sightseeing)
Osaka/Kyoto for 3-4 days
Maybe Nara/Mt. Fuji
A lot of what I'm wondering about is things like eSIMs, recommendations on places to stay, how best to navigate the trains, etc. I have a general knowledge of places to visit (TikTok is very helpful on this front somehow) but otherwise I'm clueless.
For Disney-specific questions, is a vacation package worth it? I priced one out to about $3000 for the two of us to do three days and stay at the Toy Story Hotel, but is it better to get a hotel nearby and just buy tickets? How much more will we get out of the package?
I’ve not been since COVID but here are my thoughts
I’d try to do a one trip into Tokyo if you can and out from Osaka if you can to avoid a travel day.
For your itinerary I’d start at Disney, I’ve not stayed at the Disney hotels. I have stayed at the Hilton and the Sheraton and both are great, I like the Sheraton a bit more, especially the ocean liner rooms but the happy magic rooms at the Hilton are fun as well. Take the airport limousine bus directly to your resort. I was able to buy tickets at the hotel but now I would probably book in advance direct or through klook.
Tokyo is huge so you will be traveling no matter where you stay. I stayed at the park hotel in shimbashi which was really nice, its on top of an office tower so you get amazing views. I’ve also stayed in shinjuku at the hilton but that is a lot more expensive now, unless you can get a good deal.
In kansai I would stay in Kyoto for the change of pace as Osaka,
is more like a mini Tokyo. I reccomend staying near the station, which is an attraction in itself - the granvia is nice but pricey or there is a doubletree nearby. Kyoto has a direct train to osaka kansai airport
I can’t help you with esims but I would recommend getting an IC card for transport which you can generally use on most trains.
Based on where you want to go check out the JR rail passes, they aren’t as good value as they used to be but could still be worth it if you travel a lot. Also send your bags by takubin delivery its cheap and convenient
I wouldn’t stay at Nara - you can go from Kyoto for the day. Fuji is harder to say you can stop off between Tokyo and Kyoto if you want to
Hope that helps, if you want to know about anywhere specific let me know and I will try and help