Planning a trip in August for 3 weeks

Hello All,

I plan on being Japan from August 7th to August 27th 2015. This is my first time traveling to Japan and I will be doing so with my wife for our honeymoon. We are flying into Narita and our main goal is to attend many festivals. I have done a lot of research and looks like a lot of them are at the end of August in the Tokyo Area. We are going to stay near Meguro station with my cousin.

We both love eating great food and are not much into the party scene. We would love to experience Japanese culture and are the type of people to make the most of our trip. We don't mind moving at a fast pace, but will spend a lot of time doing something we like. Here is what I sort of have mapped out:

Day 1: Arrive Narita at 4pm. Explore around Meguro, eat and rest.
Day 2: Shinjuku
Day 3: Akihabara and Harajuku (supposed to be great on Sundays)
Day 4: Tokyo Disneyworld
Day 5: Tokyo DisneySea
Day 6: Studio Ghibli (explore Kichijoji)
Day 7: Tokyo
Day 8: Travel to Kyoto
Day 9: Kyoto (Nara thrown in somewhere during Kyoto + Osaka)
Day 10: Osaka (Kita, Aquarium)
Day 11: Osaka (Minami Namba)
Day 12: Off to Kusatsu Onsen (Trying to look for hotel)
Day 13: Back to Tokyo
Day 14: Tokyo
Day 15: Tokyo
Day 16: Tokyo
Day 17: Tokyo
Day 18: Tokyo
Day 19: Tokyo
Day 20: Leaving Tokyo for Seoul

All the days I have "Tokyo" are kind of unplanned at the moment, but I know Tokyo will be my base as I am staying with my cousin near Meguro Station. I also think there will be festivals to fill in some of those days. I'm a little worried that I am not leaving enough time for Kyoto and Osaka. I hear Osaka is another big city just like Tokyo. Since I am staying for free in Tokyo, I figure I would be doing the big city things there. I am also open to suggestions on day trips from Tokyo as a base. Another big question I have is whether to get JR Pass or not. I know it's a lot of money, but it would seem that it covers our travel between Tokyo, Osaka, Kyoto and Kusatsu Onsen. We appreciate all the help!

Thanks!

Day 7 Tokyo
What does this mean? Mieji Shrine? Odaiba monogatari?

You might want to go to Kusatsu from Tokyo.
Maybe Tokyo to Kusatsu on day 7
Then Day 8 back to Tokyo or Nagoya or Fuji area. Makes it nearer to get to Kyoto.

If you are into culture and food why, WHY, WHY OH WHY, are you spending less than two days in Kyoto plus even using some of that time to go to Nara? Blashphemy!

Spending two days in Osaka is fine. Though, I think you can do all that in a day unless you are are shopaholic.
Or if you want to go to Universal Studios Japan.

A 7 day JR Pass covers roughly a roundtrip of Tokyo to Kyoto. If you add in Kusatsu and Osaka they are a plus.
Note that Kusatsu onsen isnt the only onsen town around. There a number of popular onsens in the Kansai region, around Kyoto and Osaka.

I agree that Osaka is another big city like Tokyo, just not as big. The key difference that makes Osaka popular is the different food culture. It is known as the culinary capital of Japan. Whether I agree to this statement is besides the point. You will surely find food at a cheaper price than Tokyo and some uniquely Osaka dishes too!

That said, as said previously there arent enough attractions to key me in Osaka to wait for myself to become hungry again.

You could do trips Tokyo to a number of places. If you wish to go north than the JR East Pass would be a great saver. You could easily cover many places like Yamadera, Hirosaki, Matsushima in 3-4 days.

Day trips from Tokyo include Hakone, Kamakura, Enoshima, Nikko.

For the Kyoto that you are not showing enough love to, if you are as you say making the most of your days, you could see the main highlights of Kyoto in 2.5 days. If you want a more indepth cultural experience, you would need five days (seven actually but with Osaka and a 7 day pass...). Do plan the closing and opening times of attractions. There are also attractions with no operating hours like strolling by a river lined with old houses or Fushimi Inari Jinja.

I do hope you enjoy yourself.