Schelduling problem . 14 day Japan.

My boyfriend and I are traveling to Japan for around 14 days in early June and I am completely in charge of everything. My original plan was to spend two weeks in Tokyo and traveling to popular districts and nearby locations but mainly staying within Kanto. We were originally planning on purchasing the JR East Pass for our main travel needs but my boyfriend liked the idea of the nation wide JR rail pass better since it was only slightly more expensive and was a better deal and also can be set to 14 days where as the JR East Pass is maxed out at 10. Since we decided to get the nation wide pass we thought it would be a good idea to also travel to the Kansai area like Osaka and Kyoto for part of our trip to get even more out of it. We are still limited to 14-15 days though and I am worried about the time issues, I have many places that are a must-go to in the Tokyo area so I think we would need a little over a week just for Kanto and since Kyoto and Osaka also have TONS of very good places, I need to prioritize what we are doing or at least deciding whether a trip to Kansai is even a smart idea. I would really appreciate anyone who can generally help out with the time frame and management and also possibly eliminating some similar attractions that would be found in either Kansai or Kanto or that can be put on a lower priority list. Here is a general outline of what I have so far (also, ignore budget as it is not an issue)
Kanto-
Shibuya
Harajuku
Akihabara
Odaiba
Roppongi
Ikebukuro

Ghibli Museum
Tokyo Tower
Disney Sea

(optional)
Ginza
Shinjuku
Imperial Palace/Gardens

Kansai
Osaka-Minami, Kita

Kyoto-???
Too many sights to make up my mind.

Once again, any advice/help is greatly appreciated.

If you have two weeks, I would not stick to Kanto only. Try this planner:
http://www.japan-guide.com/e/e2400.html

I personally find this a bit rushed, but it tells you that covering Tokyo and at least Kyoto/Osaka is weeeeell possible if you have two weeks.

Are you flying in and out of Narita? If so, If you buy a 7-day Japan Rail Pass and make the round-trip on Shinkansen between Tokyo and Kyoto/Osaka within that 7-day, that alone justifies the cost.

I would spend the first several days in Tokyo area (the areas you've listed under Kanto are all within Tokyo, so a few each can be covered per day!), maybe spend a day in Nikko, then travel to Kyoto, spend three days maybe there, then go to Osaka, Kobe, Himeji if you want (the castle in HImeji is beautiful), if you want to, you can go out to Hiroshima, and get back to Tokyo area on the day before your flight out of Narita. Have fun planning AND traveling!

Pls check the suggested itinerary with care and pick up what cities to visit. :)

All the places you noted under Kanto:(Shibuya,Harajuku, Akihabara,Roppongi,
Ikebukuro,Tokyo tower,Ginza,
Shinjuku, Imperial Palace /Gardens) are within the JR Yamanote loop line (Google it and enlarge the map). Most of these are really similar: Shinjuku, Shibuya, Ikebukuro, Ginza,Roppongi (google them al). They are basically shopping area with really big departments stores, thousands of small stores, restaurants, office buildings etc. you can pickup and chose only a few then visit different and more interesting places outside Tokyo like Kamakura or Nikko (1 day each). In Tokyo I would definitely see Shibuya, Harajuku (including the Meiji shrine) the Imperial palace gardens (you can't visit the Palace, unless by special appointment, and it is a bland thing)and Ginza --10 minutes walk from the Palace area--. This will take one day at a leisure pace. Another day I would see Asakusa--the funky old Tokyo--
then Akihabara (stores open around 10)then the Tokyo tower (not the most exciting place) and Odaiba. You can add Roppongi (not the most exciting place for me) the day you see the Ghibli museum.
in the Kansai: Osaka kita and minami are about 30 minute apart (by walking)see kita in the morning =early afternoon and minami in mid-afternoon and evening (especially the Dotonbori area). this will be a full day. You may be able to squeeze in the castle. In Kyoto: Kiomizu dera, the philosopher walk,the Heian shrine, the Pontocho and Gion areas (late afternoon) will take one day at leisure. Another day you could see the Fushimi Inari shrine in the morning and the Arashiyama area in the afternoon. Another day you must go to Nara. You should also go to Himeji castle one morning and stop in Kobe (Kitano area, Sannomiya, then Mosaic by the port) in the afternoon. In both Tokyo and Osaka do check the arcades (shopping streets for pedestrians only, with a roof) This is a short list..You could stay in one place only: Osaka or Kyoto as they are close to one another and your pass let you travel freely. As others have noted only buy a 7 days JR pass for the visit to the Kansai. Going to Kamakura isn't expensive at all. if you really insist on seeing all the Tokyo areas on your list that I didn't talk about you can do it in one afternoon by doing a round trip by the Yamanote and getting on/off. But, again,I would miss Ikebukuro, Shibuya, etc. and instead check Ueno, Yanaka, Shinagawa.Check this site(under Japan A-Z: Transportation/railways/ passes etc.) for day passes etc. DON'T FORGET to check Yodobashi cameras (Tokyo or Osaka) for an incredible choice of cameras, TVs etc. plus the most amazing refrigerators and washing machines (no kidding) you are likely to see plus microwave ovens that bake, broil, steam, and all sorts of things...

Yes, I was actually planning on possibly going to Nikko as well if time permitted. What I was worried about is I plan on spending most of the day at each district more or less since there are lots of places in each district I wanted to check out and I also thought I would tire easily trying to do more than one in a day. Also Disney Sea will take the majority of a day I think.

Also, I think we just wanted to do one day in Kyoto then ride back to Osaka (not much time I know) because we really just want to do two hotels instead of three and wanted more time to just explore around Osaka a little. So, I think a split in days would be, Sunday the 1st through Sunday the 8th in Tokyo, Monday the 9th through Thursday the 12th in Osaka with a one day trip to Kyoto and a return to Tokyo Friday as our flight is Saturday. Does this sound reasonable?

Mira,
What you suggested is doable. By the way, Osaka and Kyoto are close enough to each other that you can stay in Kyoto and just travel daily to Osaka, or vice versa, so you don't have to worry about changing hotels too often.
- About the different districts in Tokyo: unless you are going to explore every shop in each district, no, you will not need to (nor want to) spend one day in one district. Really, those "districts" are only a few stops away on the Yamanote train line...
- Unless you completely are not interested in traditional Japan, I would spend more time in KYoto than in Osaka :)

You can do a couple of these places in one day, eg Harajuku is best visited on a weekend afternoon when the cosplayers are there, wonderful site and they play up to the cameras. :)

There is a large shrine about 100 metres away so that is another thing crossed off your list.

Roppongi, very close to the above and again can be done fairly quickly.

Determine what you actually want to see at each location and plan around that, you'll have more fun.

Also, be prepared to walk a lot, a heck of a lot.

Hey Mira,
I'm in a similar boat as you are. I'm staying in Japan for 12 days, and half of my time will be spent in Tokyo, then 1 day in Osaka, 3 days in Hiroshima, and 2 days in Kyoto.

I'm getting the 7 day pass and activating it the day before I leave for Osaka and will be using it when I'm in Hiroshima and Kyoto, and then go to back to Tokyo.

What I would suggest for you is to get the 7 day pass, as well, and use it on the latter half of your trip.

Here's an example itinerary:

Day 1-7 - Tokyo
Day 8 - Nikko
Day 9-10 - Kyoto
Day 11-13 - Osaka
Day 14 - Back to Tokyo

If you activate your pass on Day 8, it will definitely be worthwhile.

HTH.

Mira, obviously this is your trip and you have to please yourself, not us, the armchairs quarterbacks.However when you say you want to check may places in each area you likely mean stores as Tokyo isn't the most historical or pretty city in the world. Each district (Shinjuku,Shibuya, Roppongi, Ueno etc.) is a self-contained city, with a JR station,office buildings, lots of restaurants and small stores etc. that is pretty much similar, if not identical, to the other districts. Local people mostly shop in their district and seldom go to another one, or
only for a very special event (this is the same in major towns around the world). All the big department stores have similar goods. Trust me, the 2 Takashimaya in Shinjuku and in Ginzaaren't that different, as far goods are concerned, from Parco, Mitsukoshi etc.(lots of stuff is from expensive western designers by the way) Tokyu Hands,Loft, Yodobashi cameras, Kinukuniya etc. all have several stores around town but all the stores in each of these chains have pretty much the same inventory. You will run yourself ragged running around so much and seeing much of the same everywhere. The vibes, atmosphere etc. are somewhat different in each area but it doesn't take a whole day for each. Not to mention that Tokyo isn't bargain city as far as clothes, furniture, electronics etc. are concerned..