Inspired by Sluggas post and everyone's helpful comments, I'd like to ask similar questions for family travel to Hawaii at XMAS.
I'm expecting that the seasonality of doing it at xmas may change the advice from you good people.
Having done Maliko runs and the M2M on Maui I'd head straight there, but with the family I have other considerations.
Wife (non-paddler but keen shopper and tourer), 2 teenage daughters (casual paddlers but not ocean or surf paddlers).
Anticipate hiring board(s) from Blue Planet.
2-3 weeks (gulp!)
Oahu plus one other island?

Have at it guys...thanks

Helmy not sure about weather at that time of year but if you can get to Maui it is super. I have two girls in early teens and both loved Kaanapali in Maui. The wife also loved it and she's not an adventure type. Kaanapali has a bit of everything. Enough shops , stunning beach , good places to eat , close to Laihana , and even a nice little wave on the south end .

We loved Waikiki too but to be honest when I think of my stay it always goes back to Maui. The best part of Waikiki for me was the day trip to North Shore on the "Surf Bus" tour ....not really a tour which is why we liked it and the surf out front at Canoes and Mini queens which suited my ability. Blue Planet and Nalu storage were excellent .

My wife is a keen shopper but even she avoided the outlets in Waikiki. Just can't see the point of wasting a day buying more crap that we really don't need. There's a better outlet shopping experience In Laihana Maui.

Gboots,
What's the surf bus tour?? Just checking out the North Shore or a surf trip?? Got any details... might be able to slip that into my trip too!

Not a surf trip as you think. Just a day trip to North Shore from Waikiki

northshoresurfbus.com/

"Hawaii's original North Shore Activities, Beach & Turtle Tour - The Surf Bus will take you on a full-day tour to the famous North Shore of Oahu! See Pipeline, Sunset Beach, and Waimea Bay, then get off the bus to do your activities "

Can confirm the surf bus tour went on it in 1987 and it still rocks. Best way to see the north shore espically around xmas as parking can be a problem if there is waves.
Helmy waikiki is a great place for the girls to learn to surf think a big lagoon with the most timid style waves. Also there are great places to shop, drink and just chill out,
Hawaii has a massive shoping centre just near the airport called Ala Moana (Havent been there since 87 so might have the spelling wrong). Day or two shopping to be done there.
Maui is awsome and better to sup in winter than the north shore as it will be packed with the ASP tour and surf rats. Maui is great place to take the family for a family time. I'd do three days at waikiki then 3-5 at turtle bay. week in maui and then head down to kona on the big island as the sup there is awesome with the clearest water in hawaii (think like fiji) for a week, Three different sup locations where you and the girls can sup for three weeks.
Im sure the misus will go out at waikiki. Everyone sup there. You can even sup together wife carrying with her hawaiin style for some local stoke.
How hot are your daughters, beware there will be a lot of desperate grommets looking to party with young aussie girls around this time.
Also you might want to check out hawaii university my brother in law went there on exchange and had the best couple of years of his life as they accept Australian university students on exchange, sure helps teenagers get through year 12 when they can see the opportunities that await life after school.
The north shore can be ridiculously crowded at chrissy though.