21 Day Trip in Japan

Hi Everyone,

I am looking for an Itinerary check plus people's thoughts on getting a 14 day JR pass for my wife and me for our Honeymoon. The days in Osaka and Kyoto have not been fully planned, but we are pretty sure about the days we are spending there.

Day 1: Tokyo - Land at Narita. Go to Meguro station and walk around
Day 2: Tokyo - Harajuku/Mieji Shrine
Day 3: Tokyo - Akihabara and Ueno Park, Nakamise street
Day 4: Tokyo - Tokyo Disneyland
Day 5: Tokyo - Tokyo DisneySea
Day 6: Leave early to Takamatsu. Sanuki Takamatsu Hotel
Day 7: Take Train to Tokushima for Awa Dance Festival, then go back to hotel in Takamatsu.
Day 8: Leave early for Osaka.
Day 9: Osaka
Day 10: Leave for Kyoto. Fire Festival
Day 11: Kyoto
Day 12: Kyoto
Day 13: Head back to Tokyo (time can be flexible)
Day 14: Leave early for Kusatsu Onsen Town.
Day 15: Head back to Tokyo. Check out at 10 am. Spend the day in Odaiba.
Day 16: Tokyo - Fuji Q! (maybe)
Day 17: Tokyo - Studio Ghibli Museum. Inokashira Park. Inokashira Aquarium/Zoo (Sunday)
Day 18: Hakone Day Trip
Day 19: Yokohama
Day 20: Chance to go back to any area of Tokyo we really enjoyed.
Day 21: Flying to Seoul at 6:40 pm from Narita

It looks like there is a 8 day period where we will be traveling cross country. From Tokyo to Takamatsu on Day 6 and then from Kyoto to Tokyo on Day 13. Looks like the 7-day pass would not be enough to cover both large trips. The 14-day pass may be better and then we can use it for urban transport also (along with the trip from Tokyo to Kusatsu and Tokyo to Hakone).

Thanks!

Something which might be an option is catching a plane from Narita to Takamatsu in Shikoku with Jetstar.

This might make the 7 day JR pass possible as sometimes Jetstar has really cheap fares (but check the final cost).

You should be able to only need to fly one way at the start.

Just to confirm - this is just another option and might be more convenient of slightly (not a lot) cheaper than a 14 day JR pass (taking into consideration other train options in Tokyo)

Thank you for the suggestion, mfedley. I just looked up flights to Takamatsu. Taking into the consideration the transportation fee of getting to and from the airport and then the round trip to Tokushima, I think the 14 day Japan railpass would be more cost effective. Thanks again!

A few observations -
For Harajuku, try to go there on a Sunday afternoon - that is when the youth with the wild fashions are there.
https://www.youtube.com/watch?v=3tY7jPFhTBM
For the Disney parks, they are hugely more crowded on weekends.
I think flying to Takamatsu is a great idea - it would save a ton of time and way less hassle. Be sure to see the Ritsurin Garden there - it is one of Japan's finest:
https://www.youtube.com/watch?v=afx-Ju52FiY
If you have time, going to Kotohira and visiting Konpirasan is well worth it and one of the best half day hikes you will ever take:
https://www.youtube.com/watch?v=ley9rVIewoQ
And since you're already seeing Tokyo, you can largely skip Osaka. But visiting Nara and Himeji Castle would be well worth it.
You can still see Osaka at night and enjoy Dotonbori, as well as a great view from atop the Umeda Sky Bldg:
https://www.youtube.com/watch?v=COJ_MeXbeow
https://www.youtube.com/watch?v=xb1wuyAGgyQ
For your Day 19, if you can squeeze in some of Kamakura in as well as Yokohama, you will really enjoy it. The Kotokuin Daibutsu is also very iconic in Japan:
https://www.youtube.com/watch?v=4IC8sRezqtk

I think you'll see the 21 days fly by very fast.