Gotemba and Hakone

Hi
We are considering staying one to three nights in either Hakone or Gotemba. We will want to do the Hakone circle on one day and one day, some of our group will play golf.

If we get the Hakone Free Pass, but we are travelling with luggage, would we be better to go straight to our accommodation and then commence the circle?

If we stay in Gotemba, is it a long way back to do the Hakone circle?

Would we be better to stay in Hakone and the golfers travel to Gotemba for golf?

If anyone has any suggestions how to do this, it would be appreciated.

If we get the Hakone Free Pass, but we are travelling with luggage, would we be better to go straight to our accommodation and then commence the circle?

If your hotel is not located near your entrance point to Hakone, I recommend to use Hakone's convenient luggage delivery service to get rid of your luggage (I don't think that delivery to Gotemba is possible, though). Alternatively, you could use nationwide delivery services.

Hakone luggage delivery:
https://www.hakone-tozanbus.co.jp/pdf_hp/carry.pdf

Nationwide delivery services:
http://www.japan-guide.com/e/e2278.html

If we stay in Gotemba, is it a long way back to do the Hakone circle?

Gotemba Station is about a 30 minute bus ride from Togendai, the most easily reached point along the inner Hakone circle. Note, however, that the Hakone Ropeway is currently not running due to volcanic activity. Instead, I would consider doing the larger circle via Sengoku. Sengoku is just a 20 minute bus ride from Gotemba Station.

Would we be better to stay in Hakone and the golfers travel to Gotemba for golf?

I think that staying in Hakone is better because of the hot springs, and the generally nicer scenery. As for convenience, it depends on the location of the specific hotel (whether in Gotemba or Hakone). Same for budget.

Thanks for your response. That is a great tip regarding the luggage!
Should we break the Hakone circle into 2 days - go half way around one day, have a day's break and then do the second half and return?
If so, where is a good place to stop half way?
What is at Sengoku?
If we want to return to Yokohama, is that possible using the free pass?

Should we break the Hakone circle into 2 days - go half way around one day, have a day's break and then do the second half and return?

That sounds like a good option to consider. Although, if you have people spending time in Gotemba, you could also consider leaving (and/or entering) Hakone via Gotemba instead of via Odawara (assuming you are coming from and returning to Tokyo).

I recommend to research what places in Hakone you want to see, their locations, then research good-looking ryokan and their locations and then put the entire mix of data into an efficient plan.

What is at Sengoku?

The area north of Lake Ashinoko, which is skipped by many travelers because they directly cut across ftom/to Gora by ropeway.

If we want to return to Yokohama, is that possible using the free pass?

It is possible for anybody to use the free pass. If not from their origin station, then at least from Odawara. But not that the pass may not be sold in Gotemba.

As for the round-trip version of the free pass, it can only be used from Odakyu stations. Since Odakyu does not serve Yokohama (especially not central Yokohama), you cannot use the round-trip version of the pass, at least not for the full journey.

Thanks again!
What I meant by asking about Sengoku, was to ask if there is something worth seeing at Sengoku?
If we entered Hakone from Gotemba, what would be the most efficient way to get to Gotemba?
Can we catch a fast bullet train there (that would tick that box!)
Is the Romance car a scenic route and would we be missing out on something worthwhile if we came via Gotemba?

What I meant by asking about Sengoku, was to ask if there is something worth seeing at Sengoku?

There are many museums, a pampas grass fields and a botanical garden. There is also an interesting temple. See the internet for more information.

If we entered Hakone from Gotemba, what would be the most efficient way to get to Gotemba?

Depends from where you are coming. From Shinjuku, for example, there are direct trains and buses.

Can we catch a fast bullet train there (that would tick that box!)

No, Gotemba is not served by the shinkansen.

Is the Romance car a scenic route and would we be missing out on something worthwhile if we came via Gotemba?

No, if anything, the approach via Gotemba is a little bit more scenic. But not worth any additional efforts.