Hakone 2 day Free Pass

My family and my friend's family plan to explore Hakone on a day trip only but at different dates. Can we share the use of the same pass? I will use it on Jan 9 and she will use it on Jan 10.

Hello!
You can't take Odakyu line only one stroke (from departure station to Odawara station.)
So after you come back from Hakone to Tokyo by the Odakyu line,the others can't use the pass from departure station to Odawara station.
http://www.hakonenavi.jp/english/freepass/

Have a good trip!

As the first poster says, only one round-trip to Tokyo or Odawara (depending on the pass purchased) is included. You would need to meet your friend in Hakone to swap it over!

If you enter at (say) Shinjuku the pass is retained when you pass back through the ticket gate.

Also, you can only use the pass once on the ropeway and the lake cruise - that is why they stamp it.

Trains and buses, should be no problem.

For the Hakone 2 day Free Pass including Romance Car
Can I do this?

Day 1: Shihjuku - Odawara - Hakone-Yumoto - Ropeway - Hotel

Day 2: Hotel - Gora - Gotemba Premium Outlets(by Tozan bus "M") - Shin-Matsuda (by JR Gotemba Line) - Shinjuku

Meaning that can I get up Romance Car at Shin-Matsuda instead of Odawara.
Or no choice I have to go from Gotemba Premium Outlets(by Tozan bus "L") - Hakone-Yumoto - Odawara

Thank You

I think you answered your own question when you said you wanted to use an Odakyu ticket for a JR train. JR will not accept it. (It is like turning up at JAL with an ANA ticket.)

No.

I think that he meant was to use a JR line to get to Matsuda, and walk/transfer to Shin-Mstsuda which is an Odakyu station.

Not all Odakyu services stop at Shin-Matsuda Station. You have to check a timetable to see if a specific train you wanted to catch would stop there.