Tokyo-Hokkaido Itinerary

Hi,
I am going to Tokyo-Hokkaido in coming December. Tentative schedule as below. Is the itinerary workable? Please advise for any necessary adjustment. Appreaciate for your valuable advice. :)
25/12/09
Narita Airport (08:00) to Tokyo (Hotel Check-in)
Tokyo sight-seeing

26/12/09
Disney Sea

27/12/09
Tokyo sight-seeing

28/12/09
Tokyo(~9am) to Hakodate(~3pm) (Hotel Check-in)
Hakodate sight-seeing

29/12/09
Hakodate morning market
Hakodate(~12pm) to Noboribetsu(~3pm) (Hotel Check-in)
Noboribetsu sight-seeing

30/12/09
Noboribetsu sight-seeing
Noboribetsu(~12pm) to Sapporo(~2pm) (Hotel Check-in)
Sapporo sight-seeing

31/12/09
Sapporo(~10am) to Otaru(~11am)
Otaru sight-seeing
Evening go back Sapporo (~6pm)
New year countdown celebration at Sapporo

1/1/10
Sapporo(~6am) to Niseko(~10am)
Ski at Niseko
Niseko(~7pm) to Sapporo(~10pm)

2/1/10
Sapporo(~7am) to Tokyo(~5pm) (Hotel Check-in)
Tokyo sight-seeing

3/1/10
Tokyo to Narita airport(9am)

Remark:
Using Suica & N'EX 25/12 - 27/12
Using 7days JR-Pass 28/12 - 3/1

I recommend to fly instead of taking trains. If you take Air Do to Hakodate and Skymark to return from Sapporo, the air fares won't be too bad, if you book in advance.

If you take the train, I recommend to stay the last night on Hokkaido in Niseko and return to Tokyo directly from Niseko (via Oshamanbe) instead of going via Sapporo.

Otherwise, the itinerary looks good to me.

I recommend to fly instead of taking trains.

I decided to take trains rather than flight is because of using JR-Pass is far more cheaper than airfare.

I recommend to stay the last night on Hokkaido in Niseko

Instead of staying in Niseko, what do you think about this: Travel from Niseko to Tokyo by night train.

NISEKO(~6pm) to OSHAMAMBE(~8pm)
OSHAMAMBE(~8pm) to SENDAI(~5am)
by sleeper train
SENDAI(~6am) to TOKYO(~8am)

Is it really hard to reserve for sleeper train? Especially during New Year holiday.

Another question:
I can only activate my JR-Pass once I reach Tokyo? Meaning I cannot make any reservation in advanced?

Thanks again.

Hi, you cannot activate your JR Pass before you arrive at Japan. You can only do so once you have landed in Japan. Thus, you cannot reserve seats in advance. I travelled to Japan last X'Mas and booking seats wasn't that bad, but you should plan ahead so you can do all your bookings at once

Hi! I think it's a good plan, but do keep in mind that the sun sets in Hokkaido at around 3-4pm in winter, so whatever places you want to visit in Hokkaido and you want to do it in daylight, be sure to plan it before 3pm! =)

We did a very similar journey last year, although we had a 14 day JR pass.

We took the train from Tokyo to Hakodate and stayed overnight in Hakodate, the market in the morning was very interesting, lots of king crabs too! We then did Hakodate to Sapporo, and we did an Otaru day trip too. We also travelled from Sapporo to Abashiri to take a trip on the ice breaker ships to see the pack ice/drift ice which was definitely one of the highlights. Then Abashiri to Furano, and after spending some nights in Furano we caught the trains from Furano all the way back to Tokyo in one trip, slightly longer than your Sapporo to Tokyo journey. We really enjoyed the train travel, it was comfortable and the scenery was quite interesting. Food and drink was available on board or you could pack your own, I'd recommend bringing your own book/laptop/ipod etc for the journey as it is quite long, obviously.

A few friends left Furano just before us to catch a flight from New Chitose Airport back to Tokyo, and we actually beat them to Tokyo because their plane kept on being delayed and delayed due to heavy snow and ice!

Enjoy your trip!

I think your plan is great. I'm going Tokyo-Hokkaido too. My itinerary is more or less similar to yours. And I'm living in Japan. My itinerary was advised by some J friends.