We came in via train from Kyoto (Y11,750/person), arriving in Odawara. Only planned to spend 1 afternoon + 1 evening before heading on to Tokyo. So buying a "2-day" Y3,900 pass, might not have been financially better, but it certainly was easier than trying to price out fares individually for the 5 various types of transport (train, cable car, ropeway, pirate boats, bus).
It took us about 1.5 hours to ride everything beginning-to-end (once is enough) and then a 20-min bus ride (although waiting for the bus took another 20 min) from the pirate ships dock back to downtown Hakone.
I gave 4 stars not because it's worth it, but because it's less headache than figuring out individual pricing and where to buy the tickets. Just buy the pass. Japan has a mind-numbing web of transit systems run by separate, individual companies. It'll save you headache later.
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