Which Hawaiian Island is Your Favourite?

City slickers and outdoor enthusiasts unite: Oahu is a tale of two very different pursuits.

Like any self-respecting Vancouverite, I love Hawaii. It may not have the street cred of an off-the-grid South American backpacking trip, but it’s got all the hallmarks of the quintessential Christmas or spring break—dynamite food, fun, and adventure—minus the intestinal parasites. Each island brings its own personality to the table: Maui, familiar and friendly, almost guarantees you’ll run into your neighbour in the hotel hot tub; lush Kauai is there when you’re hankering for something more rugged and outdoorsy; Lanai offers elegant seclusion; and the Big Island prefers to straddle both soft and hard adventure, with its craggy moonscape enjoyed equally well from a hostel or the Four Seasons. But Oahu? Isn’t Hawaii’s most populous island the Vegas of Polynesia, the set of Hollywood blockbusters and bus package tours? Well, yes, but it’s also ground zero for island sophisticates and some of its most wild nature. Here’s how to navigate both sides of the coin.STAYLocation is everything in Honolulu, which, unlike other Hawaiian cities, is actually a major centre with attendant headaches like rush hour and commutes. The starting point is Waikiki Beach—maybe the most iconic beach in the world, but where, at first blush, you’ll be tempted to think the throngs of tourists and the bars’ thumping bass beats are woefully short on redeeming features. But there’s great history to be had on one of Hawaii’s most perfect stretches of sand. Frequented by Hawaiian royalty in the 1800s, the beach now feels exclusive only if you’re game to rise before dawn: come 9 a.m., tourists cover the sand in an intricate patchwork of beach towels. Stake yours right outside your hotel, The Royal Hawaiian (from US$395, Royalhawaiian.com), otherwise known as the Pink Palace of the Pacific. This circa-1927 grande dame is a Moorish classic originally built for the steamer-travel crowd, but its flamingo-pink exterior is still perfectly suited to its environs today. It’s like a classic Hawaiian shirt—gaudy yet oddly normal in situ.The flip side to The Royal Hawaiian’s heritage and history is best captured by The Modern Honolulu (from US$365, Themodernhonolulu.com), a very upscale boutique hotel without the Waikiki tempo. Rimming the quieter Ala Wai Boat Harbor, these digs espouse a more subdued cosmopolitan chic, with sleek interiors frequented by the jet set and other well-groomed urbanites lounging on outdoor daybeds. The most recent addition to the Morimoto restaurant empire has landed here, where a Zen garden vibe rules—perhaps the most fitting of all the famed chef’s American outposts, since almost one in four Honolulu residents is of Japanese descent (compared to just 6.8 percent Native Hawaiian). Prices are steep, so navigate the menu accordingly.If the buzz of Waikiki holds no allure but you still want a city experience, there’s only one choice: the Kahala Hotel & Resort (Kahalaresort.com), only minutes from downtown but a world away. The resort sits oceanside in the capital’s tony residential neighbourhood of Kahala, but you’ll need to trade your stilettos for flip-flops to start the downshift. The most expensive hotel in the world when it was built, the circa-1964 mid-century resort has since hosted every sitting president as well as serving as the bar in Magnum, P.I. It’s still deluxe without any stuffiness. If you want to feel like a (very well-heeled) local, there’s no quicker shortcut.EATAnother benefit of visiting Honolulu? There’s no shortage of world-class restaurants. At MW Restaurant (Mwrestaurant.com), only a 15-minute walk from The Modern, local pastry chef and James Beard Award semi-finalist Michelle Karr-Ueoka turns dessert to socially sanctioned crack with the Hawaiian Crown Chocolate Banana Cream Pie, otherwise known as graham crackers, chocolate pudding, kinako banana ice cream, and salted butterscotch shortbread. Meanwhile, New York transplant chef Lee Anne Wong—who counts The French Laundry, Charlie Trotter’s, and Nobu as resumé fodder—opened up brunch spot Koko Head Cafe (Kokoheadcafe.com) in the low-key neighbourhood of Kaimuki. No reservations, very frequent lineups, and menu standouts like kimchi bacon cheddar scones and Elvis’s Revenge (peanut butter, banana tempura, billionaire’s bacon, local honey, toasted coconut, and a sweet bun) mean it’s time to check your dietary resolve at the door. Up the street, chef Ed Kenney (who runs the locals’ hangout Town) opened Mud Hen Water (Mudhenwater.com) in June. In here, a representation of the chef’s life through food looms—restroom wallpaper is a pastiche of tasting menus from his travels around the world. Meanwhile, the menu skews local: the luau (served with grilled he’e, or octopus) is a traditional Hawaiian dish in which luau leaves are cooked in coconut milk until they’re incredibly soft. (Kenney’s secret: he buys coconuts on Craigslist, since getting fresh coconut milk is paramount.)In Waikiki, restaurants run absurdly expensive or are of the chain variety—or both—but a block off the beach sits Bills Sydney (Billshawaii.com), where Australian chef Bill Granger’s relaxed, light-filled sanctuary serves Asian fusion with local inflections, like the sticky chili pork and peanut salad. A drive west is in order, where The Pig & the Lady (Thepigandthelady.com)—modern Vietnamese fare at communal tables—signals the rebirth of one of the U.S.’s oldest Chinatowns. And this past spring, local chef Mark Noguchi opened Mission Social Hall & Café (Thepiligroup.com) at the Hawaiian Mission Houses museum, channelling dishes he grew up with, like hand-pounded taro and Shinsato Farm pork.ROAD TRIPNotwithstanding Honolulu’s big size, the island of Oahu is relatively small, so after a few days in the city, drive north where the island vibe reigns supreme. Here, Honolulu could be light years away as you pull up to Turtle Bay Resort (US$310, Turtlebayresort.com), fresh off its $45-million facelift. Perched on the northernmost tip of the island, the hotel rocks a low-slung, sprawling design with front-row seats to its most fabled shores. The north may have the most powerful waves in the world, but stationed at the hotel, surf pro-turned-instructor Rocky Canon (and his surfing dog) will help you find the most tranquil bays, so you’ll be hanging ten (or shakily standing up) in no time. Eating options up north are majorly low-key: Ted’s Bakery is justly famous for its pies, but its under-$10 plate lunches are the real steal here. Outside of Turtle Bay is a cluster of shrimp trucks, each trying to tempt you with crevette magic—Romy’s for garlic lovers, Giovanni’s for butter fiends, Macky’s for a Vietnamese take. But the contrast between city and country, upscale and down-home, and the all-around chill ethos has never been more perfect than here and now. Image credits: Header: Kualoa-Ranch; The Royal Hawaiian: A Luxury Collection; Strawberry cheesecake: David Murphey