2 week itinerary - long enough?

Should I purchase a 7-day or 14-day JR Pass?

I'm not looking for suggestions as to certain areas I should visit within my selected cities. Only asking for advice about how my trip is structured.

I'll be staying in a regular hotel while in TOKYO for week #1, then a Ryokan for 2 days in KYOTO, then a regular hotel in OSAKA.
How's that? Can I do Hiroshima in a day then come back to OSAKA?

JAPAN TRIP (May 17th – May 31st)
May 17th – Depart from Canada
Monday, May 18th – Arrive in Tokyo, Japan (NARITA AIRPORT)
• Check into hotel.
Tuesday, May 19th – TOKYO
• (FREE TIME)
Wednesday, May 20st – TOKYO to HAKONE
• HAKONE FREE PASS
Thursday, May 21ST – TOKYO to MOTEGI
• HONDA COLLECTION HALL
Friday, May 22nd – TOKYO
• (FREE TIME)
Saturday, May 23rd – TOKYO
• (FREE TIME)
Sunday, May 24th – TOKYO to KYOTO
• Check into Ryokan.
• (1/2 DAY FREE TIME)
Monday, May 25th – KYOTO
• (FREE TIME)
Tuesday, May 26th – KYOTO to OSAKA
• Check into hotel.
• (1/2 DAY FREE TIME)
Wednesday, May 27th – OSAKA to HIMEJI?
• (FREE TIME)
Thursday, May 28th – OSAKA to HIROSHIMA?
• (FREE TIME)
Friday, May 29th – OSAKA
• (FREE TIME)
Saturday, May 30th – OSAKA
• (FREE TIME)
Sunday, May 31st – OSAKA to NARITA AIRPORT
• (END OF TRIP)

:) I like that your are making the trip to Motegi and Honda. As you are heading south there are also the Mazda (Hiroshima) and Toyota (Nagoya) sites you can visit.

Hiroshima is not too far from Osaka (a couple of hours) and you can do those as day trips.

Looks like a 14 day pass would get some good use.

If you do Hiroshima trip, then a 14-day Japan Rail Pass makes sense. However, if you are not making that trip, it does not - and not even a 7-day Japan Rail Pass make sense, because your Tokyo - Kyoto/Osaka - Tokyo round trip is done over an 8-day period, not 7.

Two weeks is never enough :) Seriously though, your itinerary looks fine. It's nice to see someone who hasnt pre planned every moment of every day. I "might" take a day from Osaka & stay the extra night in Kyoto. As others have said a 14 day pass works out if you do a trip to Hiroshima and it's well worth doing.