Tokyo or Kyoto - which one first?

I will be arriving in Narita on Dec 21 at 8pm, and planning on visiting Tokyo and Kyoto before leaving for my 6:30pm flight back to Canada on Dec 28. I'm unsure how I should arrange the most efficient and hassle-free itinerary. I saw that there is an overnight bus from Narita to Kyoto, but I'm not interested in that option. Ideally, I would have liked to get to Narita earlier, so we can go straight to Kyoto and then end our trip in Tokyo. Now, arriving late in Narita makes it less convenient to head to Kyoto first, unless it's the next morning. If we end up staying the one night in Tokyo before heading to Kyoto the next morning, which area/hotel would make it the most convenient?

I recommend to go to Kyoto first in order to avoid the holiday rush between Tokyo and Osaka, which starts on December 27.

In other words: I recommend not to travel along the Tokyo-Kyoto route on December 27 and 28, because it will be very busy. The evening of December 26 will also be busy.

21st - arrival at NRT(8pm) and checkin the hotel in Narita city.
22nd - early checkout, activate JR pass, NEX and Shinkansen to Kyoto, check in the Kyoto hotel, Spend the day in Kyoto
23rd - Kyoto
24th - Osaka or Nara or Himeji(depends on your interest)
25th - Kyoto accomodation or departure for Tokyo
26th - early checkout to Tokyo from Tokyo, or Tokyo
27th - Tokyo
28th - Tokyo, depart for NRT in the afternoon

your travel is covered by JR pass under this itinerary.
Enjoy your travel

On the assumtion you will use a Japan Railpass, you can't make it to Kyoto from Narita on the day of arrival.

Last connection:
NRT 18:46 - 20:01 Shinagawa 20:10 - 22:56 Kyoto

http://gutereise09.blogspot.com/2008/09/train-connections-be...

You might stay in Shinagawa considering you will use both Narita Express and Shinkansen.

If you want to get to Kyoto as soon as possible, you can catch the first Shinkansen Hikari from Shin-Yokohama.

Shin-Yokohama 6:00 - 8:01 Kyoto
In this case, you might stay in Shin-Yokohama or Yokohama Area.

http://www.hotelpricefinder.com/
http://travel.rakuten.co.jp/en/