What pass should i use?

Hi Lee Wei,

Thank you for writing down your itinerary so carefully, this makes it much more easy for me to look at possible options.

When a JR Pass is would be beneficial depends on if you fly to Hokkaido or take the train. Flying is a lot quicker but may cost more and you do have to go trough flying procedures a couple of times (Personally I find that rather frustrating). To give you an idea of rail travel. The full trip Tokyo - Sapporo takes 10 hours, you can however make a stop at any time and get to see more of Japan. Nice stops directly on the route include Sendai, Hachinohe, Hakonedate and Nobori-bestsu. Whether plane or train is better is up to you, the JR Pass does cover all train travel to and within Hokkaido.

The JR Pass does not cover the metro/subway, it does however cover the local train network in both Osaka and Tokyo, which is more than enough to see most of both cities.

Hope this helps,
Daniel