JRPass

Hi there,

Firstly for your trip the only rail pass that will make any sense is the nationwide Japan Rail Pass. These come in 2 flavours that are applicable to you: 7 day (¥28,300) and 14 day (¥45,100). You'll need to spend more than this on individual JR tickets to make them worthwhile so lets take a look at your approximate costs:

1. Haneda > Tokyo: ¥500
2. Tokyo > Kyoto: ¥13020, (164mins, 513km)
3. Kyoto > Narai: ¥9010, (208mins, 301km)
4. Narai > Kansai airport: ¥11360, (308mins, 443km)
5. Narai > Nagiso/Nakatsugawa: ¥10240 4 x return trips at ¥1280 each (you must get the local bus to Magome or Tsumago, please note that only local trains stop at Narai, the Shinano Wideview departs from Shiojiri and takes longer and double the cost of the local train option)

TOTAL: ¥44,130 for 3 legs

As you can see your total JR ticket cost is very very close to the cost of the 14 day rail pass, coming in at ¥970 cheaper. I think if I was in your situation I would pay the extra ¥970 and opt for the flexibility of the 14 day free travel on JR, this should give you the flexibility to change your plans, and also will mean you don't have to bother with tickets and so on during your trip. Also, if you really do want to use the Shinano Wideview (which costs double the local train each journey), you can do so at no extra cost.

Hope this helps!