Hi CEJ, Nice to see a fellow Aussie here!
It's normal for people who have limited time and opportunities for travel to create itineraries with lots of lodging location changes in an effort to fit in all the amazing places they'd like to experience. But many discover that it makes for an unnecessarily disorienting and tiring trip to have their lodging in different cities in a foreign country every one to four days.
Frequently changing hotels means frequently spending time and energy locating and checking in to your hotel and unpacking and repacking your bags. It also means frequently having to learn your way around another unfamiliar transportation network, neighborhood and personal living space. Being in such a different country as Japan can be disorienting enough without the challenge of frequently relocating from one city and hotel room to another.
Some people do fine with this, and maybe you already know it works for you. But if you're not a seasoned traveler, you might be surprised how this travel style affects you and your travel partners.
The distances between the places you want to go are small enough that they can all work out as day trips from two or three major cities. So it might be worth considering basing yourself in one city, and in the same hotel, for at least a third, if not half or more of your trip. From a well-chosen base, you'll be able to access countless wonderful experiences, including the places on your tentative itinerary, or others you'd find equally enjoyable, without having to be uprooted frequently.
For example, you could base yourself half the time in one hotel in one city in the Kansai region (maybe in either Kyoto or Osaka) and the other half in one hotel in one city in the Kanto region (maybe in Tokyo). If you were to do that, your itinerary should be no less full and enjoyable, but much more relaxed. Like this:
Nights 1 to 8: Hotel in Osaka or Kyoto Day trips in Osaka, Kyoto, Hiroshima, Nara, Miyajima, Himeji, Koyasan, etc
Nights 9 to 15: Hotel in Tokyo Day trips in Tokyo, Fuji Five Lakes, Izu Coast (e.g. Jogasaki Kaigan), Nikko, Hakone, Kamakura, Yokohama, etc
When you're based at one hotel for a week or so and the weather interferes with one of your day trips or you find a day isn't enough to do everything you'd like to do at one of your destinations, you'll have the flexibility to change your itinerary, e.g. schedule another day trip to the same place, etc.
If you want to be sure you fit in all the items on your current itinerary you could split your lodging dates between three cities instead of two, with nights 1 to 5 in Osaka or Kyoto, nights 6 to 10 in Toyama (from which you could do day trips to Shirakawago, Takayama, Kanazawa and the Alpine Route) and nights 11 to 15 in Tokyo.
Izu is really a special place, and I encourage you to make it one of your day trips from Tokyo. The coast is so beautiful, even the train ride down the coast is stunning. If you like getting out in nature, izuhike.com has a fantastic coastal hike at Jogasaki Kaigan.
In case you end up going to Fuji Five Lakes, which I highly recommend, bike tours there are not to be missed. I did the tour of two of the lakes with fujibiketour.com, and it was my favorite day of my trip to Japan. On a clear day it really is that kind of place where you can't take a bad photo. Mt Fuji is lovely from there, especially at sunrise and sunset with the lakes in the foreground.
Hope you have a really wonderful trip!
Kristina
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