Hakone day trip

Hi,

Me and my partner are traveling to Japan very soon for 3 weeks.
During this time we want to do a day trip from Tokyo to Hakone (on the 25/12/2019 Merry Christmas :) ! )
We plan to buy the Hakone 2 day free pass with round trip from shinjuku included.
We have a private onsen booked for 4pm that same day at Hakone Yuryo that we cant be late to.
I have been to Japan before for holidays and as an exchange student (my partners first time to japan) but I have not been to this area before so I am a bit unsure on what to do.
I just have a few questions because I couldn't find some information when researching this area:
1. Will we be able to complete the Hakone loop before 3pm? (in time for our 4pm onsen) If we leave shinjuku at around 7:30am, or would we have to leave wayyyy earlier?

2. We are more interested in doing the loop clockwise as we would like to see the shrine first before any crowds start gathering there later in the day or is it better just to stick to anti clockwise ?

3. If we should do it clockwise, what would our loop look like? I've tried planning the loop myself in clockwise but it is currently 3am in Australia and my brain is not working, please helpppppp! haha. (sorry silly questions I know)

4. We are not that interested in the boat ride part of the loop. Can we skip that and save time? If so, how?

I think the main thing I need help with is what a itinerary for the day would look like if we skipped the boat ride and HAD to be back at Hakone-Yumoto station by approx 3pm, either clockwise or anti clockwise?

Sorry I know I wrote way too much in this and if there is any spelling mistakes please forgive me for my 3am potato brain.

THANK YOU SO MUCH FOR YOUR HELP!!!

1. Will we be able to complete the Hakone loop before 3pm? (in time for our 4pm onsen) If we leave shinjuku at around 7:30am, or would we have to leave wayyyy earlier?
No.

2. We are more interested in doing the loop clockwise as we would like to see the shrine first before any crowds start gathering there later in the day or is it better just to stick to anti clockwise ?
No. I always do clockwise - better connections, less waiting. I've always been quite unimpressed by the Hakone Shrine.

3. If we should do it clockwise, what would our loop look like? I've tried planning the loop myself in clockwise but it is currently 3am in Australia and my brain is not working, please helpppppp! haha. (sorry silly questions I know)
Same as anit-clock-wise but opposite direction. Note there is a replacement bus Gora back to Hakone-Yumoto - no mountain train for a while yet.

4. We are not that interested in the boat ride part of the loop. Can we skip that and save time? If so, how?
Not really. If you skip the boat, then you could skip the ropeway too to head to Gora, but many people want to visit Owakudani, so getting to the far end of the lake is a requirement. Also, if you skip the boat (and take a bus or taxi), then the "Free Pass" starts to be poor value/more expensive than individual tickets.