I grew up on Oahu, so I love it unconditionally. But each year, many visitors are startled (read disappointed) to find that Oahu is really a booming metropolis replete with traffic jams, a busy downtown, and beaches packed cheek-by-jowl with salmon-colored tourists. People expecting a virginal tropical paradise on Oahu are 40 years too late.
Of course, all the guidebook activities -- such as visiting the Arizona Memorial at Pearl Harbor, catching a dolphin show at Sea Life Park, and learning about our royal Hawaiian past at Queen Emma Summer Palace -- are recommended for a reason: They are fantastic family experiences. As a kid, I made yearly school field trips to all three.
To those who grew up here, Oahu is like those oysters they sell to tourists at the International Marketplace: With the right tools you can crack it open and find a pearl. For instance, the island is home to nearly 600 named surfing spots and 80 hiking trails. And with very little effort you can take up either activity as if you'd been born to it.
For surfing, get the family down to Waikiki Beach, just behind the giant bronze statue of Duke Kahanamoku, the father of modern surfing, where you'll find two different surf stands offering lessons and rentals. The beach boys who teach there are an institution, and for about $35 they basically guarantee to have you surfing within an hour. While Bella was far too young, fairly small children can enjoy the waves, provided they can swim. Just ask the beach boys about a tandem lesson, in which the child shares a board with the instructor. My uncle taught me to surf this way in these very waters when I was only 3 years old.
Our recently renovated hipster hotel, the Waikiki Marc (to be renamed Bamboo in December), is one block from surf and sea. The two-minute walk to the beach saved us a significant amount of money and caused no inconvenience. The hotel is decked out with a cool, retro-look pool and offers plenty of rooms and suites with kid-convenient kitchenettes.
Inland, two mountain ranges, the Waianaes and the Ko'olaus, make up the framework of Oahu, with houses built right into the valleys. One day, we followed a fertile streambed in a residential valley choked with strawberry guava trees, passion fruit vines, and ginger varietals to three swimmable pools. The hike was no more difficult than a walk, and after about half an hour, the malls of Oahu seemed remote. The Hawaiian Trail and Mountain Club and Sierra Club can point you to trails suitable for families; both groups lead hikes regularly.