When to Activate JR Pass

Hello,
I will be in Japan for 14 days but am trying to determine if I need a 7-day or 14-day JR Pass.
If I only get the 7-day pass, I would take the Airport Limousine to the hotel. What I am unclear on is if it would be worth getting a 14 day pass to be able to activate earlier and utilize within Tokyo city limits or if this is needed?

Narita ---> Tokyo
Tokyo - Day 1-4
Tokyo --->Hakone
Hakone - Day 4-6
Hakone --->Kyoto (was thinking of activating 7 day pass on this day)
Kyoto - Day 6-10
Kyoto-->Osaka--->Kyoto
Kyoto--->Tokyo Disney
Tokyo Disney - Day 11-12
Disney --->Tokyo
Tokyo - Day 13-14

Thank you!

JR pass won't help much in Tokyo. It mostly only works on 2 of the many subway lines, and paying regular fare is only 240-300yen anyway. And it won't have much value for Hakone, as JR doesn't have trains all the way there. The difference between the regular Hakone Pass and the one that just goes from where JR stops is only 1000y or so.

A 7 day pass could work for you, but honestly since you are only going between Tokyo and Kyoto/Osaka, you will come out way ahead by just booking a discount round trip Shinkansen ticket through a tour agency. For example: https://www.japanican.com/en/tour/detail/PAS1J02031MKC/

Going between Tokyo and Osaka is very cheap if you avoid the bullet train (and that's only about a 15 minute advantage anyway), so you don't really need a pass for that. And likewise, the JR pass doesn't cover subways in Osaka or Kyoto.

I'd probably just get a PASMO or SUICA in Tokyo when you arrive and load about 5000y on it to start. You can use that prepaid balance for any subways, buses or short train rides in pretty much all of Japan add money later if needed. Then buy Airport transport seperately, use Hakone Free pass for Hakone, and then either 7-day Rail pass or discount Shinkansen ticket I linked to for Kyoto and back.

For your itinerary as now planned,
a 7-day Japan Rail Pass can pay off,
saving your cost a little,
compared to the JR regular cost;
a 14-day Japan Rail Pass would never pay off.

Officially there is step to activate a Japan Rail Pass.
When you receive your Japan Rail Pass,
you set the day when you will start to utilize the pass,
which you cannot change for any reason.
Gate machines do not handle Japan Rail Passes.

Hakone is not accessible by JR.
You will make a side trip from Odawara.
https://www.japan-guide.com/e/e5206.html

Narita Airport [NRT] and Tokyo Disney Resort
are actually outside Tokyo Metropolis.

What is the date of your Day 1?
Have you decided the areas where you will stay overnight?
(Your transportation modes depend on the location of lodgment.)
Have you confirmed that you cannot choose Haneda Airport [HND]?

Sorry, a silly typo is found in my previous response.
The word "no" is missing in
"Officially there is step to activate a Japan Rail Pass. ";
it should be:
"Officially there is no step to activate a Japan Rail Pass. "

@omotenashi You are of course right that there is no official step to "activate" the JR Pass but many of the major sites that sell them use that terminology so it's something you will keep seeing. For instance this page, if you scroll down to the "how do I use section" step 3 is shown as "activate" https://www.japantravel-centre.com/transportation/japan_rail_pass/

Stan Norrell:
many of the major sites that sell them use that terminology

One possible misunderstanding caused by the word "activate"
is to think as if you had something to do
when you start to use your Japan Rail Pass
so that the pass should be active.

Actually there is no such step.
You set the first day for your Japan Rail Pass
not when you start to use the pass
but when you receive your pass.

Me2:
JR pass won't help much in Tokyo.
It mostly only works on 2 of the many subway lines,
and paying regular fare is only 240-300yen anyway.

Subway line are non-JR lines, where no JR pass works.
The lowest subway fare (per adult passenger) in Tokyo is 165 yen.

Going between Tokyo and Osaka is very cheap
if you avoid the bullet train
(and that's only about a 15 minute advantage anyway)

I am not sure what this clause (in the parentheses) means.

The difference between Shinkansen and non-Shinkansen trains
in time required for you to travel between Tokyo and Shin-Osaka
is by far larger by 15 minutes.
It is a comparison between 2 and a half hours and over 8 hours per way.

If you are only using it for Odawarra/Hakone to Kyoto and Kyoto to Tokyo. A seven day pass wont pay off. Unless you can find 4000 yen of travels elsewhere in those seven days. Just to break even.

I would just use one way tickets for your shinkasen travels. And Suica/Pasmo for all you subway/private railway travels in Kanto and Kansai.

hakata14:
If you are only using it for Odawarra/Hakone to Kyoto and Kyoto to Tokyo.
A seven day pass wont pay off.

I agree.
My simulation shown in the former response
is on the condition that you start to use the pass
when you leave Tokyo,
not when you head to Kyoto as you say.

On which day will you go back to Tokyo?

@omotenashi
The yamanote and chuo line (in Tokyo) are functionally the same as subway lines, and work with the JR pass. Those are the two I was referring to. The fares I mentioned are what I paid for typical trips.

And thanks for catching my typo, I meant travel between Kyoto and Osaka is cheap and does not require shinkansen or Jr pass.

"functionally the same"???

Why just those two and not the others? They are not particularly special.

And you do know the Chuo line extends more than 400 km and goes all the way to Nagoya? I usually just use the first 40km, and even for Tokyo only know one subway line that runs far (the Metro lines top out at 30.8km, and Toei gets to 40.7km for the Oedo line.)

I feel like you are getting hung up on semantics a bit much here. If you want to use only the JR pass in Tokyo to visit the typical tourist spots, you will either be riding a lot of the Yamanote loop, or occasionally using the Chuo line to cut through the middle of Tokyo. That's why I mentioned those two and said they can function like subways. I realize the Chuo line goes well outside Tokyo, but that's irrelevant to someone trying to get from, say Shinjuku to Tokyo station.

If you notice in my original post, I did not recommend relying on a JR pass only, so I'm not sure why this needs to be argued further. IC card and picking the fastest or simplest route across any rail option in the city is the best way to go.

I actually like the fact Chuo line shortcuts the Yamanote line - I used it yesterday with a guest for Odawara then Tokyo and then across to Shinjuku and as a terminal station (Tokyo), it is a good place to board the Chuo line to ensure a seat (fortunately school holidays makes the trains less crowded this week). I .was just confused why one train line was being compared to another like a "subway" when they both seem to provide/operate largely the same way

Oh, and as an addition, there are some "typical tourist spots" in side Tokyo that actually do cost quite a lot to visit where a JR pass might help. I did one of my usual trips today (for a meeting) that was a JPY2,000 round trip. And some of the within Tokyo day options I have suggested to guests are in the 2-3 thousand yen range round trip so those passes do have some value.