My itinerary

Good evening everyone,
I am currently planning my third trip to Japan, and would like your thoughts on my plans.

21-23 : Arrival in Tokyo
23-25 Yokohama
25-26 Hakone
26-27 Kanazawa
27-28 Takayama
28-29 Nagano
29-21 Niigata
31-3 Sendai - I plan to spend a whole day going to the Fox Village near Shiroishi.
3-4 Fukushima
4-6 Tokyo

I'd switch Kanazawa and Takayama around to save a little travel time.

Thank for the input !

You might want to write up a list of things you want to do in each location, and allocate your time accordingly. Some of those destinations are much more interesting and full of things to do than others (but of course it all depends on your interests).

For example, I ran out of things to do in Takayama after one day, and left early to spend an extra day in Kanazawa. I ran out of things to do in Fukushima City after about an hour, and I'm glad I hadn't booked a hotel for a full day there. OTOH you could spend weeks in Tokyo and not run out of new things to see and do, and Yokohama and Kanazawa are also full of stuff to see.

Personally, since you're coming from Yokohama, I'd do 1 night in Hakone since you can do an awful lot of the loop on your arrival day and on the 2nd day do some of the loop/whatever you missed and then continue on by bus to Kawaguchiko and stay there one night, that way the next day you can catch the 8 am bus to Takayama. Takayama is all right, but it can just take a long time to get there. From Hakone you're going to need to get to Odawara to catch a train to Nagoya and then take a bus or train from Nagoya. It's easily going to be 4-5 hours. Because of back tracking Kanazawa really wouldn't save you that much time and Takayama to Nagano is a lot longer than Kanazawa to Nagano.

I happen to really like Nagano and never feel like I have enough time there. I also really enjoyed Matsumoto and Kanazawa, so I'd personally probably skip Takayama and do more at one of those 3 cities, but I am also not particularly fond of the countryside.

I do a lot of day trips from Tokyo to Ononimachi and I've seriously thought about spending the night in Koriyama or Fukushima just to shorten the train trips, or I've just thought about a rental car so I have more freedom.

I admit, while I don't enjoy bouncing around, I would consider looking to see if there is a group tour on Japanican or if there is a ryokan in the vicinity of the Fox Village that does/pick up drop-off. It's like 14,000 yen just in a roundtrip taxi fare to and from the village from the nearest shinkansen station. I can't remember which ryokans offered but I could have sworn some offered shinkansen station pick up and drving to and from the fox village.

Enjoy your trip!