Oahu, Hawaii’s Mythic Paradise, Goes Cosmopolitan

Travel + Leisure

Around 8:30, a warm rain began to fall on Honolulu’s monthly night market, but no one seemed to mind. Not the crowds swarming the food vendors up and down Cooke Street, not the bikinied models strutting the runway for the local boutique Bamboo Sky, not the multitude of leashed, smiling dogs — and not me. I was fresh off the plane, sitting on a curb devouring a bowl of noodles and lemongrass tofu. The scene was pleasantly cacophonous, with grumbling generators, shouted food orders, and the competing beats of several DJs. Teenagers leaned against streetlamps and ate gourmet mac and cheese with chopsticks. Couples strolled while sipping lemonade from huge Mason jars adorned with stickers that said ALOHA.

A piece of conventional travel advice passed among mainlanders goes like this: Hawaii is wonderful, but avoid Honolulu. It’s just a city.

No, no, no.

True, Honolulu is a real city, one with rush-hour traffic and a thorny homelessness problem and some unfortunate 1960s architecture, but there’s no place like it. The emerald Koolau Range rises up at its back, mounded with fluffy clouds; the turquoise sea sprawls at its feet. Rainbows appear without fanfare, linger, dissolve. Coconut palms abound, as do magnificently domed monkeypod trees, white-blossomed frangipanis, royal poincianas with flame-red flower crowns — all of it rustling in the trade winds. Even Honolulu’s white concrete towers, gridded with balconies, have a certain tropical charm. Here, almost halfway to Asia, is an American urban center, distinctly exotic but distinctly familiar, too, down to the revitalization happening in some of its once-gritty precincts.

Consider Kakaako, the neighborhood that hosts the night market. Just southeast of downtown, it has a light-industrial history and a cinder-block aesthetic now softened by colorful murals and a new abundance of inviting shops and restaurants. Sleek condominiums are going up, along with lively mixed-use complexes. Within one block, one might visit Paiko, an airy florist meets coffee shop; the cozy cocktail nook Bevy; the taqueria Cocina; and Hank’s Haute Dogs, purveyor of elevated wieners. And that’s before you settle in at the open-air, wood-and-steel taproom of Honolulu Beerworks. “Kakaako has a great feel to it with all the small businesses in the area,” said Geoff Seideman, founder of Beerworks. “We wanted to build a community gathering place.”

I heard several Oahu residents describe Kakaako as Honolulu’s answer to New York’s Williamsburg, usually with a hipster-disavowing roll of the eyes but also with unmistakable pride. Honolulu isn’t kitschy, they were telling me. It’s neither a provincial backwater nor a theme park for tourists. Honolulu is its own place. Honolulu is cool.

Chinatown has lately become the embodiment of this. “It still has an edge,” Mark Pei, cofounder of the creepy-fun curiosity shop and gallery Hound & Quail, told me. “There’s a lot of history here.” The streets were quiet on the Monday evening I visited, almost deserted. Pei was right about the history. The flat, frontiersy façades of some of the buildings hint at the brothels and opium dens of the past, and the now-extinguished neon sign for 1950s girlie joint Club Hubba Hubba conjured the ghosts of carousing sailors. Other structures are exuberant architectural mishmashes: Italianate, Art Deco, pagoda. I passed shuttered produce wholesalers, tattoo shops, a window advertising Chinese herbs, another displaying crystals and feng shui items. Brick, an unusual building material for Honolulu, is everywhere in Chinatown, preferred by developers after earlier incarnations of the neighborhood were largely destroyed by fires in 1886 and 1900. The bricks themselves arrived on ships from the mainland and were swapped out to make room for cargoes of sugarcane.

At the intersection of Smith and Hotel Streets stand two of the city’s most talked-about restaurants, Lucky Belly and Livestock Tavern. Both are co-owned by Dusty Grable and Jesse Cruz, and both feature exposed brick and unfussy but elegant cuisine. (Sitting at the polished Livestock bar in the last of the evening light, I ate delicious pasta with sea urchin in a golden, creamy sauce.) No stranger to reinvention, Chinatown has in the past century gone from thriving immigrant enclave to seedy red-light district to punkish no-man’s-land to, it seems, gastronomic frontier. “The charm, the grit, the character, the culture,” Grable said about why he chose Chinatown. His vision for the area, like Seideman’s for Kakaako, is inclusive and collaborative. “What we love most,” he said, “is the sense of community in working toward making it a destination neighborhood, not just individual venues.”

Indeed, the immediate vicinity of the Grable-Cruz mini-empire practically demands a post-dinner bar crawl (with a de facto theme of exposed-brick interiors). Manifest, on Hotel Street, has a large chalkboard devoted solely to whiskey options. Bar 35 across the way dazzles with its panoply of craft beers. Hank’s Café around the corner has a divey vibe and a cozy second-floor jazz venue called the Dragon Upstairs.

Emerging into the warm night after my last stop, I paused, getting my bearings, a little spooked by the contrast between the lively indoors and the empty street. Old-fashioned streetlamps cast down pools of yellow light. A couple of raggedy street kids jumped on and off a bench, laughing raucously. Suddenly one of them loomed in my face, pale, with dilated pupils. “Do you know where you’re going?” he asked.

“Yes,” I said, though I did not, quite. Purposefully, among the ghosts of sugarcane cutters and rowdy sailors, I walked on. I am glad to have been here before this place turns into something else.

“Avoid Waikiki” is another piece of advice you’ll hear, but I have a soft spot for it. Sure, Honolulu’s most famous beach is chockablock with hotels and bristling with selfie sticks, but everybody seems to be having such a good time. And what a beach it is: a long crescent of white sand lorded over by the reclining bulk of Diamond Head, ruffled by rolling waves long and low enough to beckon even the most novice surfer. Catamarans and outrigger canoes steer out through the swell. Sightseeing helicopters buzz overhead, sweeping by the iconic panorama.

After lying by the pool at the Halekulani hotel on Waikiki Beach, drinking a mai tai garnished with a purple orchid — the very fantasy of Oahu — I meandered down Kalakaua Avenue, Waikiki’s main shopping drag, at dusk. Masses of people in bright alohawear drifted in and out of boutiques and malls like fish in a glossy reef, buying up goods that have chugged here on container ships and will soar away in the baggage holds of airliners. Louis Vuitton. Apple. Quiksilver and Billabong. The ubiquitous ABC convenience stores peddled sunscreen and cheap souvenirs. I passed the statue of surfing pioneer Duke Kahanamoku, his bronze arms draped with fresh leis. Beyond, the sky had gone tangerine over silver water, and the disappearance of the sun behind the long, flat horizon reminded me just how much ocean was surrounding us, here on this volcanic blip in the world’s most geographically far-flung island chain, on our little raft of commerce.

I ended up at Yoshitsune, a hotel-lobby hole-in-the-wall across the street from the beach. Grandmotherly servers with limited English but immaculate kimonos clacked around in wooden sandals, serving sashimi, house-made tofu, sticky gobs of fermented soybeans, steamed egg custards in ceramic pots. Everyone else was Japanese, and I felt briefly disoriented, as though I had stumbled through a portal to a neighborhood joint in Tokyo.

The next morning, a mere two miles away, I felt as though I were in Damascus — specifically in the 18th century. I was on the Honolulu Museum of Art’s tour of Shangri La, a house built by Doris Duke in the late 1930s just east of Diamond Head and filled, over the course of 50 years, with a world-class collection of Islamic art. There are Persian tiles from the 1200s; a Mughal-style bedroom inspired by the Taj Mahal; a dining room designed to resemble an imperial tent; a luminous ceramic mihrab, or prayer niche, for which Duke outbid the Metropolitan Museum of Art. The Damascus Room was one of the last stops: a dim, close chamber of antique painted panels. Through the dark lattice screens that cage the windows, only the glimpses of electric-blue waves and wispy clouds gave away that I was in Hawaii.

Oahu has this effect, of seeming like many places and eras at once. Sometimes you are in Middle America and sometimes you are in Asia. Sometimes you are in a gleaming, pan-ethnic Pacific Rim future and sometimes in a retro resort paradise invented by 1960s travel agents. The island’s fiery prehistory looms in the form of the Koolau and Waianae mountain ranges, eroded remnants of shield volcanoes inactive for millions of years. At Pearl Harbor, the USS Arizona, sunk in 1941, still bleeds oil. A complex native culture and heritage underlies all of it, ancient but alive. The island has absorbed and hybridized the influences of visitors since the first Polynesian seafarers arrived more than 700 years ago, so why should it stop now?

I drove east over the Koolaus and followed the Kamehameha Highway north along the coast. I passed clapboard churches, schools with jalousie windows open to catch the breeze, homemade signs advertising fresh lychees and pickled mango, the sheltered waters of Kaneohe Bay. KEEP THE COUNTRY COUNTRY! exhorted a banner strung along a fence. Old-timers sat on their lanais, watching the breakers roll in.

Once I rounded Kahuku Point, I was officially on the North Shore, surf spot of legend, where every winter big waves kicked up by Aleutian storms make the long trip south to pound Sunset Beach, Banzai Pipeline, Waimea Bay, the whole coast. An annual migration of elite riders follows. High-level surfing is a paradoxical pursuit, its practitioners characterized by a chilled-out countercultural vibe but also by a consuming obsession, and the North Shore, even in summer, has a correspondingly mixed mood, both mellow and relentlessly single-minded.

“Big-wave surfing is what put the North Shore on the map, and there isn’t a more famous collection of surf breaks anywhere in the world,” said Jodi Wilmott, a 16-year North Shore resident and general manager for the World Surf League. “The ocean is central to the Hawaiian lifestyle, and surfing is a major expression of that.” Surfing draws thousands of people (and their money) to Oahu every year, from big-name pros to clueless spectators like myself, and it also brings Hawaii to the world. Even the most dedicated and distant landlubbers can find themselves unexpectedly beguiled by surf films, surf fashions, surf slang. The North Shore is, as locals say, country, but it’s also an international port of call; it’s a peaceful place, and it’s a near-mythical place of pilgrimage.

Shrimp trucks and fruit stands dot the roadsides. Surfers — dudes and chicks, kids and graybeards — walk the shoulder with boards under their arms, occasionally sticking out a thumb for a ride. In the town of Haleiwa, tourists buy frozen açai bowls from thatched-roof stands, peruse surf shops, sign up for surf lessons. Locals hang out and talk about waves, about real estate, about trips off-island.

“That you can be as visible or as invisible as you choose” was how Wilmott described what she loves about life on the North Shore. “That you can be truly adventurous — hike, climb, dive, surf uncrowded spots — so close to home; that it attracts very creative, artistic, eclectic types; that you are half an hour from the city and an international airport while being a thousand miles from care.”

The recently renovated Turtle Bay Resort certainly felt like that. It is the only big hotel on the North Shore and is a resort-y resort, with lots to do: horses and helicopters, golf and tennis, snorkeling and surfing, restaurants of varying degrees of formality — the kind of place where you could imagine a Dirty Dancing-style romance flourishing. The hostess at my beach cottage greeted me with a lei and a hug, and after a dinner of fish with coconut sauce at Lei Lei’s, a low-key restaurant beside a golf course, I slept with only a screen door between me and Turtle Bay itself, lulled by the sound of crashing surf.

On my way to Sunset Beach in the morning, I grabbed oatmeal and a coffee from the Sharks Cove Grill food truck and then sat in the sand and watched the surfers. Even with the relatively gentle summer swell, Sunset is a serious spot, but the wet-suited figures shooting through aquamarine barrels looked relaxed, at home in the waves. I envied their skills, their boldness. Though I am a SoCal native, I never learned to surf, and so (When in Rome! she thought dorkily) I scheduled a two-hour lesson with North Shore Surf Girls, a local outfit founded nine years ago by women’s surfing pioneer Carol Philips.

The next morning I bobbed in the beginner-friendly waves at Chun’s Reef while Kat McGill, my 23-year-old instructor, hung on to the back of my board and radiated good cheer. “Okay, we’re going to get you a wave,” she called. “Ready?”

“Sure,” I said, less than sure.

“Paddle, paddle, paddle!” She kicked with her fins and gave me a helpful shove onto a breaking wave. Dutifully, I paddled, then pushed up from the board with my arms so I was speeding along while doing a sort of cobra pose on a steep slope of white water. “You got this!” Kat yelled from behind, ever the optimist. “Stand up!”

As I had practiced on the beach, I attempted a sort of ninja hop onto my feet, landing with knees bent, one arm forward, the other crooked at my waist. For a moment, I didn’t fall. Under my board, a shallow, rocky reef sped by. Underneath that — slowly, slowly — the Pacific Plate pulled the island away from the lava-spewing hot spot that formed it. Behind me, open water stretched more than 2,000 miles to Alaska. Ahead was the beach, the parking lot full of jeeps and rental cars, the road. Beyond the road unfurled Oahu with its palm trees and waterfalls and pleated volcanic mountains, its jungled canyons and the red-clay soil of the Dole pineapple plantations, its bungalows and beach mansions and hotels and military bases, the white towers of Waikiki, then more ocean, only ocean.

In another second, I fell, of course, flat on my back into the water, but for all the different ways to see Oahu, all its myriad angles, I was pleased to have glimpsed it, however briefly, from a surfboard.

The Details:


Halekulani: A sleek Waikiki oasis that fronts a small nook of beach. halekulani.com; doubles from $525.

Turtle Bay Resort: Recently renovated to the tune of $45 million, this busy resort has everything from horses to helicopters. turtlebayresort.com; doubles from $280.

Restaurants and Bars

Bar 35: A beer hot spot in Honolulu’s Chinatown with more than 200 ales, porters, and lagers from 20 different countries. bar35hawaii.com; pizzas $13–$17.50.

Cocina: A taqueria led by chef James Walls incorporating local produce and meat. Kakaako; cocina​hawaii.com; entrées $8–$13.

Honolulu Beerworks: Choose from the list of local brews at this breezy open-air taproom in Kakaako. honolulu​beerworks.com.

Hank’s Haute Dogs: Popular haunt offering creative takes on an American favorite. Kakaako; hanks​haute​dogs.com; hot dogs $4–$6.

Lei Lei’s: turtle​bay​resort.com; entrées $24–$37.

Livestock Tavern: At the vanguard of Chinatown’s rebirth, this restaurant serves a seasonal menu of stick-to-your-ribs cuisine in a rustic, inviting space. livestock​tavern.com; entrées $16–$32.

Lucky Belly: A trendy ramen shop, complete with a late-night takeout window. Chinatown; lucky​belly.com; ramen $9–$14.

Manifest: Mixing cocktails that keep aficionados returning, this bar has a chalkboard dedicated specifically to whiskey. Chinatown; manifest​hawaii.com.

Paiko Florist and Coffee: Shop offering hands-on floral workshops and locally sourced plants. Kakaako; paiko​hawaii.com.

Sharks Cove Grill: A permanently parked food truck peddling hearty surfers’ smoothies, sandwiches, and grilled skewers. Haleiwa; sharkscovegrill.com; entrées $4.50–$13.

Yoshitsune: A little piece of Japan tucked into the Park Shore hotel that has delicious omakase dinners as well as an array of à la carte options. Waikiki; parkshore​waikiki.com; entrées $9–$48.


Honolulu Night Market: The third Saturday of every month, food vendors and local merchants set up shop on Cooke Street in Kakaako. honolulu​night​market.com.

North Shore Surf Girls: A predominantly female team of instructors provides group and private surf and paddleboard lessons on the North Shore. north​shore​surf​girls.com.

-Travel + Leisure Staff

Similar Posts by The Author:

Leave a Reply