Will the Kansai area pass work if i’m departing from Tokyo to Kyoto and then to Osaka, then from Osaka back to Tokyo?
The hint is in the name The Kansai area pass works in Kansai only - it doesn’t work in Tokyo or anywhere between Tokyo and the Kansai area. Osaka and Kyoto are both part of the Kansai region though, so you can use it when you’re down there. The only passes that include the Kanto area (around Tokyo) and the Kansai area (Kyoto, Osaka, Nara, Kobe) and allow you to travel between them are the JR Pass and the Hokuriku Arch Pass (with a big, but lovely detour to the Japan Sea coast). If you need more flexibility and you aren’t planning to go to lots of places apart from Tokyo & Osaka/Kyoto, you could just buy regular tickets for the Shinkansen and use a Pasmo/Suica/Icoca prepaid card to get around.