So, I have been to Japan 4 times now. In that time, I've passed Fuji on the Tokaido Shinkansen a total of 7 times, been round Hakone, and have visited multiple tall buildings on that side of Tokyo and... Nothing.

Until my most recent visit, where my son acted as a lucky talisman and we saw it, finally, from the Skytree. For about 15 minutes. Then it was gone again for the rest of our trip (including the train to Nagoya).



Anyway, as others have said, it's very hit and miss, and a bit of a way from Tokyo. My choice would be to head from Shinagawa to Odawara on the Shinkansen and then do a mini-circuit around Hakone, so at least if the mountain's being shy, you don't have a wasted trip. But realistically, that's going to be a full day.