Autumn Osaka - Kyoto - Nara - Kyoto - Nagoya - Kyoto - Takayama - Osaka - Kobe - Osaka
This is my first Japan trip and I will be flying to Osaka during early Novomber.
I had drafted my itinerary as below:
Day 1 (1st Nov)
Day 2 (2nd Nov) (Kansai Pass)
Day 3 (3nd Nov) (Kyoto Pass)
Day 4 (4th Nov) (Kyoto Pass)
Day 5 (5th Nov)
Day 6 (6th Nov)
Day 7 (7th Nov) (Kansai Pass)
Day 8 (8th Nov) (Kansai Pass)
Day 9 (9th Nov) (Kansai Pass)
That's a very nice itinerary and you've done your planning very well. I checked the route for the best tickets/passes and would advise buying normal tickets for your travel to Takayama and back. A normal ticket is around 10,000yen for one way but there's not really a pass which would get you there in good time on the same day. The JR Pass covers the route but there's not enough in ticket prices to make savings with it.
2.) The main difference between the JR Pass and Kansai Pass is the area of useability. The Kansai Pass is only valid within the Kansai area, while the JR Pass covers all of Japan.
Enjoy your travels,
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