Q: Should I get a 14 days JR pass for my travels through Kanto and Kansai Area? I am looking to hit the important places between Tokyo and Osaka. I would be flying in and out of Tokyo.
A: Your 14 days travel in Kanto and Kansai area is what our classic 2 weeks itinerary route in Japan suggests. The route is:
Tokyo -> Kamakura -> Kyoto -> Nara -> Osaka (Himeji) -> Tokyo
In my experience, JR pass is rarely worth it unless you plan to travel to many places that are far from one another in a short time. In the case of the classic 2 weeks itinerary in Japan, we are covering quite a number of places in just 14 days but they are not that far apart. Assuming that you plan to only use the train for all the travels, for its quickness, comfort and convenience, then let us take a look if it is worth to buy a 14 days JR Pass or to buy individual train travels as you go.

Japan train / Shinkansen travel with JR Pass. Photo by Peter Broster
I have always used Google maps to help me with my transport planning in Japan, it shows you everything from the time schedule, all the possible connections and their prices. I really recommend to use it for your transport planning in Japan.
Tokyo to Kamakura train – around 900 – 1,100 JPY
Kamakura to Kyoto train – around 13,000 – 15,000 JPY
Kyoto to Nara train – around 900 – 1,500 JPY
Nara to Osaka train – around 700 – 900 JPY
Osaka to Himeji train plus return – around 3,500-7,000 JPY
Osaka to Tokyo train – around 14,500 JPY
Rough total of individual train travel prices is around 35,500 – 39,000 JPY (348 – 383 USD)
The cost of a 14 days JR Pass is 62,950 JPY (618 USD).

Japan Rail Passes in train. Photo by Geoff Stearns
Here we get a clear idea that we should not be getting a JR Pass for our 2 weeks classic itinerary. Also, a tip is, as mentioned in our one day trip to Himeji, you buy a Suica Pasmo Card or individual regional passes like Kansai Pass to help you to further save money.
Related articles:
Is JR Pass worth it for 7 days (1 week) visit?
Classis 2 Weeks Japan Itinerary