June Summer Trip

[hibarirei]

My friends and I have been planning a two week trip to Japan. We've narrowed down the dates and have decided to focus ourselves in Tokyo just for ease of travel. The three of us are seniors in high school and I'm the one with the most Japanese language-proficiency.
I've studied Japanese for six years and am planning on attending college in Japan. All of us have been to Japan before, but not without an adult or a tour guide.

We've decided on June 13-June 28th. The days themselves are able to be changed, give or take a day, but we're trying to plan things with those days in mind just so that we have some consistency. We'll be staying in the Khaosan Ninja Hostel in Tokyo, mostly because it's cheap. Have you heard of it?

Anyways, we have a few things planned out and we're trying to be generous in planning our itinerary (giving a full day or so to each attraction). However, we also wanted to visit Osaka. Would you suggest landing in Osaka, spending a day or two there, and then migrating up to Tokyo?
Or would it be better to stay in Tokyo and then arrange a long train trip down, then back up when we finish our sightseeing there?
This is also a much asked question, but any suggestions for sightseeing places in Tokyo and Osaka/Kyoto that are less famous? To put it bluntly, my friends can only stay interested in temples for so long. I'm assuming shopping and food places would be far more fun for them.

That being said, would you guys happen to know of cheap airline tickets? On average, things I've found are $1100-1200. I know that's rather standard, but I've also seen that last minute tickets are around $800. It might be stupid, but would it be alright to wait until closer to June to look up our tickets? We're booking rooms at a hotel as soon as we can, but if our flight days change, we'd be stuck with paying for the differences.

Any suggestions about saving money would help a lot, as well!

[JohnBraden]

From the States, most flights land at Narita and to a lesser extent, Haneda, so beginning in Osaka will add a domestic flight to your trip for starters. If you're traveling by train to Osaka, it's best to fork over the 28,300 yen for a 7 day JR pass since it would pay for itself on that round trip. You can use the pass on the JR lines in Tokyo: Yamanote, Chuo, etc. You can't use it on the Marunouchi Line and some others.

For food, it would have to be Osaka and shopping, Tokyo....

I don't know if Odaiba is in your itinerary or not, but it has a few attractions, such as Toyota Mega Web (a giant showroom with simulators, etc.), Joypolis (a giant amusement/arcade center), Decks and AquaCity (shopping malls), etc. It's on the man-made island across Rainbow Bridge. If you find yourself spending a rainy day in Tokyo, hop on the Yurikamome line and spend the day there, along with half of Tokyo!