Which route to take in Japan? (Natives or people who are really familiar with Japan only!)?

Question:

I am visiting Japan in the 2nd last week of December and the entire trip is 2 weeks long. My friend and I are planning to fly to Tokyo, Narita and then take the shinkansen to some other place, travelling through different places first before ending the trip back in Tokyo.

Am starting to plan the route now but has no clear idea on how to go about it since it's our first trip there. Our main destinations would most likely be Hokkaido Kyoto, Osaka, Nara, Yokohama, Chiba and Tokyo.

1) Which is the best order for my route? Was thinking TOKYO - HOKKAIDO - KYOTO - OSAKA - NARA - YOKOHAMA - CHIBA - TOKYO

2) Do you think 2 weeks is enough to visit all these places? If yes, do you think we could squeeze in Aomori and Nagoya after Hokkaido?

3) (optional) Lastly, any food you think we MUST try in these places?

Thanks for answering my question!

Answer:

If you really want to go all over like that, then you should look into either getting a JR Rail Pass, or an airpass like JAL's Yokoso Airpass or Welcome to Japan Fare, or ANA's equilvalent. You need to get them before arriving in Japan though.