JR pass for Japan itinerary?

Hi all, been wondering if there are any ways we can rely on just a 7day JR pass? My itinerary is:
Day 1 - Day 3: Tokyo
Day 4: Tokyo to Hakone and stay one night
Day 5: Hakone to Kyoto
Day 6 - Day 9: Kyoto, Nara, Kobe etc
Day 10: Kyoto to Osaka
Day 11: Osaka
Day 12: Osaka to Tokyo
Day 13 - Day 15: Tokyo

Seems like we need to activate the JR Pass when we travel from Hakone to Kyoto, and the last usage day would be Osaka back to Tokyo, which means a total of 8 days of JR pass usage. Would it make sense to buy a 14 day JR pass or a one way ticket from Hakone to Kyoto?

Thanks!

Unless you make some major side trips not mentioned in your initial post, regular tickets will come cheaper than a 14-day Japan Rail Pass.

Your 7 day JR Pass will end on Day 11 in Osaka, and not on the day of the return to Tokyo.

If the OP starts using the pass on Day 4, the final day would be Day 10.

14-day JR pass would make no sense, since your not staying enough time, and since the 7-day pass won't work because of your itinerary, I recomend for you to buy the tickets instead. But may I ask you something? Have you bought your flight tickets? I would recommend a multi-city flight, instead of doing all the transport and going back and forth. For example, landing in Tokyo and departing in Kansai Airport. I saw that you have the last days in Tokyo, but you could move those days to the start of your itinerary. I believe this way will be better for you, you could save some money and travel time. For the days in Kansai area you could check the regional JR passes for Kansai.

Enjoy your trip!

Thanks all! The intention was to activate our pass on day 5 when we travel from Hakone to Kyoto as I believe we don't need to use the JR trains to travel from Tokyo to Hakone.

My flights are already booked in and out of Tokyo, so unfortunately won't be able to change that.

Seems like I should get a one way JR ticket from Hakone to Kyoto on day 5 and activate the 7 day JR pass on day 6 to 12?

If you buy a one-wat ticket to Kyoto, then the 7 day pass is too expensive for the rest of your trip.

Just buy single tickets. It works out about the same as the 7-day pass (a little more, but not much). Plus, you can do things like Kyoto to Shin-Kobe without transferring at Shin-Osaka if you take the shinkansen option and non-reserved is also a good option for a trip like that (Y2,810 vs Y3650 on the Nozomi service).

Just buy one way tickets.

Seven day pass wont work as you need it for 8 days to pay off. And fourteen day pass just wont pay off the whole trip.

Since you are keen on using a JR pass, I recommend to check out the website Hyperdia. Hyperdia will show you the price between locations on train/bus and that way you can see if it's worthy to purchage a pass or buy single tickets.