I really enjoyed my time on all of the islands I have been too. Will be making my way to Oahu and Kauai this year.
So far my fav. adventures on the islands was a night time hike over the old lava to watch the new lava go into the ocean on the Big Island, Napili 18 mile coastal kayak trip on Kauai, and a helicopter ride on Maui. Haven’t been to Oahu yet but I am hoping to have some kind of adventure there as well.
The answers to a couple of questions could solve the dilemma:
How old is you child?
What time of year do you plan on going?
If your child is young and you are going near the summer months your best bet may be Oahu, staying in Waikiki. There are many advantages to this:
You wake up early and get a surf in at Canoes or Queens and get back before anyone can complain about how you’re not spending enough quality “family time” on vacation.
You can easily teach the wife and child how to surf there so that may share or at least understand your sport more.
If your child is really young the sheltered beach is the safest on the island for him/her to play.
And if you get fed up with town, the north shore is a short drive away.
I´m planning to stay in the Islands at least 15 days with family (if they don´t wan´t to come, I will not stay hungry with them…eheheh), and propably I will stay in countach with some of you to help to get the best of it…
I intend to go maybe in the beginning of December to get some waves, see the waves and the best of turistic places.