I've travelled quite a bit in Japan, both with myself, and with other people. Everyone has different travel styles. In my case, I think that any destination can be fun if you are with fun people, but if I'm travelling alone, I'm more careful to go to interesting places that will be fun to explore even by myself. As an example, I loved visiting Izu peninsula with my friends, but if I went by myself, I think I'd be less interested.
That said, here's my list of cities/regions I have been to that I think would be interesting to visit even by myself, and places I would prefer to go with someone else. I don't mean to say that, say, Tokyo wouldn't be more fun with other people, or that you couldn't enjoy Nagano by yourself. This is purely subjective. For example, I don't really care to go to festivals or hot springs by myself, whereas I'm quite happy wandering around shopping streets or pretty natural areas alone.
By yourself:
Tokyo
Yokohama
Enoshima (good day trip from Tokyo/Yokohama)
Kawasaki
Hakone
Kyoto
Osaka
Kobe
Nara
Hiroshima / Miyajima
With other people:
Sapporo Snow Festival (note: I went here by myself, and it was *really good*, definitely worth a visit even if you're travelling by yourself; but a festival is really the kind of place where it's more fun with friends)
Izu peninsula (good weekend trip from Tokyo/Yokohama)
Okinawa
Nagano
Niigata
Nikko
Mt Fuji
Gifu, seeing ukai etc
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