HI there,
For a 14 day pass to be economical you need to spend over ¥45,100 on individual JR tickets. Lets take a look at the ticket costs of your itinerary:
- Tokyo > Nagano: ¥8170, (108mins, 222km)
- Nagano > Obuse: ¥8170, (108mins, 222km)
- Obuse > Nagano: ¥8170, (108mins, 222km)
- Nagano > Matsumoto: ¥2970, (51mins, 62km)
- Matsumoto > Nagoya: ¥6070, (132mins, 188km)
- Nagoya > Inuyama: ¥6070, (132mins, 188km)
- Inuyama > Nagoya: ¥6070, (132mins, 188km)
- Nagoya > Kyoto: ¥5640, (37mins, 147km)
- Kyoto > Osaka: ¥540, (28mins, 42km)
- Osaka > Kyoto: ¥540, (29mins, 42km)
- Kyoto > Nara: ¥690, (45mins, 41km)
- Nara > Kyoto: ¥690, (44mins, 41km)
- Kyoto > Tokyo: ¥13420, (161mins, 513km)
TOTAL: ¥67210 for 13 legs
As you can see, with a 14 day Japan Rail Pass you'll make a saving of ¥22,110 over individual tickets. I can certainly recommend you purchase a 14 day Japan Rail Pass.
You can look up train timetables and costs for all of your legs at the Hyperdia travel planning website and learn how to use Hyperdia for Japan Rail Pass holders through our video blog.
Hope this helps!