12 day itinerary

Hello,
First of all, thank you for the great postings on this forum. Very helpful!
My husband and I (early 30's) will travel from the U.S. to Japan Sept. 22-30. We will visit Tokyo and Kyoto, then fly to Hokkaido to visit my brother who is living in Japan and teaching English through the JET program. Sept. 29 the three of us will travel back to Tokyo. My husband leaves on the 30th and my brother and I will spend a few extra days touring in and around Tokyo.
This is our first (and possibly only) trip to Japan, so we have planned a packed agenda in order to see as much as possible. We are both young and energetic, interested in nightlife (but not dance clubs), history, scenery, good food, and culture (experience as opposed to museums).
I've posted our itinerary below. Flights and basic itinerary are set, but hotels, tours and day trips are up for grabs. Would appreciate any and all suggestions. I realize this is a long post, so thanks in advance for any assistance.
Evie
Japan Itinerary 9/22 ・10/4
Sat 9/22
Fly BHM to Tokyo (NRT)

Sun 9/23
Arrive Tokyo NRT airport 5:35 p.m.
Stay at Palace Hotel Tokyo

Mon 9/24
Private tour of 杜odern・Tokyo 8 a.m. ・4 p.m. Chris Rowthorn Tours
Giants baseball game at Tokyo Dome 6 p.m.
Nightlife suggestions?
Stay at Palace Hotel Tokyo

Tues. 9/25 7:30 a.m.
Nozomi train from Tokyo to Kyoto
Arrive Kyoto station mid-morning
Stay at Hyatt Regency Kyoto
Evening walking tour through Gion district 4-6 p.m (Kyoto Sights and Nights)
Dinner ・nightlife suggestions?

Wed. 9/26
Private tour Kyoto 9 a.m ・5 p.m. Chris Rowthorn Tours
Classic Higashiyama Area
Evening plans?

Thurs 9/27
6:22 a.m. Haruka train from Kyoto Station to Kansai Airport
9:45 a.m. flight Kansai to Obihiro (Hokkaido)
Will stay at bed and breakfast in Hokkaido

Fri 9/28
Day in Hokkaido
Visit school, brother痴 host family, etc. ・and do laundry!
Dinner with brother's friends

Sat 9/29
2:05 p.m. flight Obihiro to Haneda (Tokyo) ・Arrive 3:40 p.m.
Stay at Royal Park Hotel Tokyo (for easy access to T-Cat next day)
Evening Kabuki one act, dinner, drinks, nightlife, other suggestions?
Sun 9/30
Dave flys home ・depart Narita 3:10 p.m.
Matt/Evie tour Tokyo
B Roppongi Hotel Tokyo
Check out Roppongi nightlife
Mon 10/1
B Roppongi Hotel Tokyo
Day trip KamakuraKamakura
Evening suggestions?

Tues 10/2
Trip to Nikko or Hakone ・overnight stay
Suggestions? Hotels? Restaurants?
Wed 10/3
Back to Tokyo
B Roppongi Hotel Tokyo (question - should we stay again in Roppongi, or would it be better to stay in another area of Tokyo?
Afternoon and evening plans?
Thurs 10/4
Afternoon flight to U.S. ・depart Narita 3:10 p.m.

I bet people are afraid to comment because you are already so organised.. I do question why you stay in hotels where people are likely to be westerners and take guided tours. I prefer to stay in local hotels, wherever I go (I didn't say cheap- i said local). i understand that a guide will give you a full history of places etc. but I so love wandering around areas that I read about when preparing my trip and finding small treasures (places, stores, etc.)that aren't must see at all. I also fear that I may not click with my guide and that our tastes are widely different. Also I find it so easy to get around in Japan-no I don't speak the language-
I noticed that you have a whole afternoon free on your first day in Kyoto? do take the train from Kyoto station to Fushimi-Inari shrine (only one stop away) it is a great place.
my idea of night life is just wandering around . As for restaurants, I go wherever I see a majority of locals. but eh! it's your trip, not mine. But
don't plan eveything ,take the time to relax and enjoy the unexpected. Depending on the weather your energy may go down a lot too!

I see no problems with your itinerary. Unfortunately, I am not a nightlife person, and have no valuable suggestions for evening activities.

You are right - I may have overplanned. Thanks for the advice about just soaking in the country! I'll try!

Hi Evie, if you are free in Tokyo, try visit their Imperial Palace. Very nice gardens. Best of all, its free. But they only conduct tours in Japanese, i think. You need to apply in advance. "http://www.kunaicho.go.jp/e17/ed17-03.html"

Evie and Sam,
Just to make it more clear: You will need a permit from the Imperial Household Agency to enter the area of the Imperial Palace with a group. This tour will let you pass by the building of the Imperial Household and the side of the Imperial Palace where the New Years greeting takes place. NO visit of the inside of any building, no visit of the garden behind the palace. But you can visit free and without prior permit the East Garden of the Imperial Palace, what is a fine Japanese landscape garden.