Getaway Guide: 48 Hours in Oahu, Hawaii

It's time to give the paradise pioneer another look.

 Westerners love Maui…and who can blame them? But let’s not forget that it was big brother Oahu that started tourism in Hawaii. And the island is right in the middle of a welcome reinvention as it sheds a tourist-tarnished reputation for being a wall of high-rises and gets serious about being a high-end hot spot for sun, surf, shopping and plenty of spectacular sights. The very chill scene at the Modern Honolulu pool. FridayTake a deep breath as you step into the clean white lobby of the Modern Honolulu: the broken surfboard 3D collage jutting out of the wall behind the registration desk delights the eye, and the heavenly custom plumeria scent is an olfactory reminder that you’re now officially on vacation. The Modern eschews the Hawaii Five-0 shtick in favour of hip simplicity: an urban boutique hotel with an ocean view. Though the daybeds that line the aquamarine pool beckon, you’ve got a date with your balance. The north shore of the island is where the serious surfers hang ten, but for the beginner—you—the calmer currents of Waikiki Beach are good training grounds. A lesson with Hans Hedemann Surf School is a worthwhile investment—you get to skip the dull paddling and just let the unsettlingly tan 20-something instructors tow you out to the sweet spot. Catch waves all afternoon, and then trade your wetsuit for evening wear; tonight, you splurge on the four-course tasting menu at Chef Mavro, run by the jolly George Mavrothalassitis, a Marseilles-born, James Beard award-winning cook with a penchant for the fresh island ingredients of his adopted home. Share bites of spicy bigeye tuna with rich, tangy sea urchin and pepper aioli, and finish things off right with a scoop of Hawaiian goat cheese ice cream topped with spoonfuls of tart strawberry-rhubarb jam and honey candies. Not ready for the evening to end? Hop in a cab to La Mariana Sailing Club for a nightcap served up with a delightful hit of retro tiki chic; sip enthusiastically garnished Zombies beneath twinkling lights, bamboo thatching and the watchful eye of vintage South Pacific carvings. Make a stop at Leonard’s Bakery for some delicious Portuguese doughnuts.SaturdayBrave the line at Leonard’s Bakery—you’ll need a box full of their famous malasadas to fuel your day. The warm Portuguese doughnuts are served up dusted with sugar (plain—or cinnamon, if you feel like getting a little crazy) and bursting with creamy custard filling. Make sure to wipe your fingers clean before you start exploring Kalakaua Avenue’s Luxury Row and Royal Hawaiian Center, a winding, palm tree-lined boulevard of tony shops (Hermès, Tiffany and Co. and the like) trafficked by spend-happy jet-setters from abroad. Join their ranks with a spree of your own—maybe a new Kate Spade wrap for beach time later on?—or window shop and save your money for a decadent bamboo massage at the Mandara Spa at Hilton Hawaiian Village; shoots are soaked and heated in essential oil and rolled along your back to smoothly melt away any surf-induced knots. Ready to get a move on? You could head to Diamond Head and get stuck on the climb up in a gaggle of infuriatingly unequipped lookeloos, or literally take the road less travelled for a more unique experience. Bike Hawaii hosts Bike and Hike treks on their own private trails, which means you’ll have the path—and the gorgeous waterfall at the end—all to yourself, and the views as you speed down the winding mountain road on a vintage cruiser will be unencumbered. Reward yourself for your adventurous spirit with dinner at Iron Chef Morimoto’s eponymous restaurant. It’s a favourite of the Obamas when they’re in town, and that’s no surprise: the menu and ultra-mod room, decorated with moss-covered tables and artsy, oversized pieces of coral, are both impeccably done. Order plates of rich tuna topped with savoury dashi foam and spicy-sweet avocado wasabi sorbet, delicate slices of Wagyu beef served up carpaccio-style with pops of ginger and soy, or the fresh yellowtail buri bop, cooked right at the table in a hot stone bowl. Cap off the night with one last drink or two at The Study at the Modern: try the Fire Across the Sea, which spices up Grey Goose with a touch of wasabi and horseradish, or the sophisticated strawberry-and-honey-based Champagne Haze. Treat yourself with some relaxation from the Mandara Spa. A beautifully presented plate from Iron Chef Morimoto’s restaurant.SundayHop in the rental car and head north for a scenic drive past Hawaii’s most spectacular shores. Keep your eyes peeled for pro surfers attempting to tame the monstrous waves as you make your way to grab lunch at Romy’s Kahuku Prawns and Shrimp. Plates are piled high with plump shrimp smothered in lemon and garlic; there are hundreds of shrimp trucks peppered throughout the island, but Romy’s is the only one that raises its own key ingredient. Before you head back to the real world, there’s one last thing on your Hawaiian to-do list: “swimming with the dolphins” is a bit cliché, but following a wild pod through the deep blue is a breathtaking experience. Hitch a ride to the dolphins’ local hangout with Wild Side Specialty Tours, strap on a snorkel and try to keep up.