What to do in Oahu
Home to the Pearl Harbor national monument site, storied Waikiki Beach and the cosmopolitan city of Honolulu, Hawaii's most populated island is also one of its most vibrant. Of course, if you only spent time on the bustling southern shore you'd miss Oahu's quieter, more laid-back charms, like the North Shore's surfer beaches and the lush landscape of the Waimea Valley.
Where to go in Oahu
Waikiki Beach might be famous for surfing, but lessons here can feel crowded. Instead, book a 40-minute outrigger canoe ride with Waikiki Beach Services, and learn more about these stable, powerful boats that have been part of Hawaiian and Polynesian history for centuries. On the way out, parents and crew will need to seriously paddle to slice through the waves, but heading back, it turns into a serious thrill ride as you're pushed towards the shore.
The teaching pros at the Hans Hedemann Surf School consider themselves experts in working with kids who've never ridden a board before. It's worth heading up to their North Shore location at Turtle Bay Resort, where lessons are taught in a sheltered cove that offers plenty of fun, rideable swells. Thanks to the instructors' encouragement, most kids (and adults!) are able to stand and ride at least one wave by the end of the lesson — or many more, depending on how fearless they are.
A must-stop on any North Shore visit is Waimea Valley, an original Hawaiian ahupua‘a (land division) that extends from the mountains down to the beach, and was once presided over by Hawaiian kahuna (high priests). The area, which includes hiking trails and a botanic garden, is home to many historic and sacred sites, including a 40-foot waterfall — where swimming is permitted — that's easily reached by either walking up a ¾-mile–long paved road or riding the shuttle.
Where to stay in Oahu
Sleep off your jet lag at the freshly renovated Prince Waikiki, where every room and suite overlooks the water, and the massive floor-to-ceiling windows are more like see-through walls. It's a quick drive or walk to the northern end of Waikiki Beach, although it's tempting to park yourselves on the hotel's 5th floor sundeck, where the infinity pool seems to merge with the sparkling Ala Wai harbor below. Poolside hula lessons are offered twice weekly, and the bar serves kid-friendly drinks like guava juice and strawberry lemonade, along with more potent ones for parents, like the fruity, tequila-based Marina Sunset and Kona Longboard Lager from the Big Island.
The Four Seasons Resort Oahu at Ko Olina, which curves around a delightful blue lagoon on Oahu's east coast, has figured out a key truth: Keep the littlest guests happy, and their parents will want to book their next trip before they even finish the first one. Kids are spoiled from the second they step into their room, and depending on their age, treats might include a cookie to decorate (complete with frosting and other fixings), a stuffed animal on the bed and their name spelled out with colorful bath sponges. Daytime activities like swimming, sandcastle building and jewelry-making at the resort's stylishly fun Camp Kohola are included in the room rate, and there are special themed parties, like crab spotting on the beach, during the evening. Super-independent kiddos can also sign up for overnight glamping sessions from 6 p.m. to 8 a.m. They'll sleep on the spa's rooftop tennis courts in tents with cushy bedding (this is still the Four Seasons, after all) and enjoy dinner, s'mores, stargazing and a movie, plus a pancake breakfast the next morning.
Where to eat in Oahu
You'll be waking up early anyway, so you might as well save one morning for breakfast at Liliha Bakery & Coffee Shop on Kuakini Street near Chinatown, a locally loved breakfast stalwart since 1950. You shouldn't be discouraged if the counter seating is full — you can also ask to wait for a "back of the house" table inside the kitchen and watch the bakers in action. Don't miss the pancakes and hot buttered rolls, and if you order an omelet, be sure to swap your white rice for the sublimely flavorful garlic fried rice. Even if you don't make it here for breakfast, stop in and fill up a bakery box with treats: Liliha's coco puffs (chantilly-topped choux pastries filled with chocolate pudding) are known as the best on the island, and their malasada doughnuts are also legendary.
It may sound strange to come to Hawaii and head to a mall for lunch, but hear us out: The Lanai at the Ala Moana Center is not your typical food court. There are 10 mini restaurants here, and they represent some of Hawaii's tastiest and most creative offerings, including shave ice from Uncle Clay's House of Pure Aloha, the utterly Instagrammable Mahaloha burgers, handheld sushi snacks from Musubi and boba (tapioca) smoothies from Maui's HiTea.