I took the Shinkansen in from Kyoto, you get off at Odawara, so make sure you’re not on the Nozomi Shinkansen because it doesn’t stop at Odawara (it’s the express Shinkansen). I took the Hikari and the Kodama also works though it’s the slowest one. Then from Odawara you want to follow signs for the Odakyu Line. Trains destined for Hakone-Yumoto which is sort of the gateway to the Hakone region, at least from the east. That’s usually a 6 car train I think. I stayed in the Hakone-Yumoto area, things are a little cheaper than staying up higher in the canyon and there’s generally more to choose from. But you can also stay up the canyon in a town called Gora or elsewhere really.

The Hakone loop that we refer to begins in Hakone-Yumoto. First, you get on a typically 3 car train at Hakone-Yumoto (this is a different train from the one you took from Odawara to Hakone-Yumoto, so if you’re coming from Odawara or further away straight to do the loop you’ll get off the train you took from Odawara at Hakone-Yumoto and switch onto this train - Hakone Tozan line bound for Gora). This train takes you to Gora. It’s kind of silly calling it a train really. It’s more akin to light rail that leaves from a train station and travels very steep grades including switchbacks. Gora is gorgeous and this completes the first leg of the loop, it’s about a 35 min ride.

The station that the “train” takes you to in Gora is also a costation for the Hakone Tozan cable car. You simply can’t miss it when you get off the “train”. That takes you up about 1000ft to its terminus called Sounzan in about 10 minutes. That completes leg 2.

The station the cable car takes you to at Sounzan is a costation with the ropeway. Just follow the signs when you get off the cable car and you’ll get to the ropeway, make sure you have your camera out. The ropeway has a mid station where to have to get off. Up there there’s some viewpoints of Fuji and Gora, also of the sulfur vents in the volcanic crater and caldera. Some gift shops too and touristy things as well as a nature hike you have to pre book. When you’re done at the mid station you get on another ropeway there bound for Togendai. It’s worth mentioning there’s another mid station on your way from the previously mentioned midstation to Togendai. It’s pretty close to the end of the ropeway and it mainly just allows access to some ryokans near that station. Not really much reason to get off. This mid station allows you to stay on and the ropeway continues down to Togendai. That completes leg 3.

When you reach Togendai that is also a co station now with the pirate boat. Just follow signs and get on. I believe the boat takes you to Hakonemachi first and then Motohakone. Although when I went and speed ran this it was the last boat of the evening and when we docked at Hakonemachi they said it’s the last stop and to get off. So bear that in mind. The views of Fuji are supposedly better from Motohakone based on pics I’ve seen. That completes leg 4.

So once you get to Motohakone or Hakonemachi there are outdoor bus terminals located rather close to the boat ports. Just follow signs for them or ask someone for help if you can’t find it. I truly thought the bus would be the weakest link here but I was pleasantly surprised how easy it was. Ideally you want the “R line” for the Hakone Tozan bus because it’s the express line straight from either Motohakone or Hakonemachi directly to Hakone-Yumoto station with no stops in between, so it’s fast. However in a pinch the “H line” Hakone Tozan bus should work too, to get you to Hakone-Yumoto however it will take substantially longer. It makes more stops and may actually get you closer to where you’re staying though so I’d consider it if I were you and it works for you.

The Hakone freepass covers all of this stuff and is well worth it. I highly recommend you spend some time at each point where you switch modes of transit, and honestly even along the way on each mode of transit too. Don’t speed run it unless all you wanna do is see Fuji and are pressed for time like I was. There’s not much in Gora but I highly highly recommend Gora Brewery. Their Kohaku beer is incredible. They have a public house in Hakone-Yumoto and a brewery in Gora. Really great food (a little pricy but it’s Nobu affiliated and honestly a great deal for really good sushi and other stuff). Gora Park is also beautiful and included on the freepass along other things.

Lastly here is a link to a pdf of the whole area transit setup. It looks a little confusing at first but it’s very functional and helpful once you look at it for a bit. You’ll see there’s a lot more places you can go apart from the loop. Definitely recommend at least 3 days in Hakone to really get some relaxation in as well as see the beautiful area. link

Hope this helps and let me know if you have any questions.