The towers of Waikiki Beach cast such long shadows over Oahu that it seems daunting, in the mind’s eye at least, to escape them when weighing a visit to Hawaii’s most populous island.

But it can be done, and we did. Odysseus-like, I lashed my hands to the mast of a Kia Optima for a week this spring while my family crew and I motored around the island’s perimeter, ignoring Waikiki’s siren song. We planned a clockwise path from the evolving resort area of Ko Olina to the laid-back North Shore to the breathtakingly beautiful windward (eastern) side to the doorstep of the Diamond Head State Monument.

Less than a tank of gas later, we had seen and experienced aspects of Oahu that we had underappreciated — or been blissfully unaware of — during previous trips.


Looking back, as I search for words to capture nearly deserted gold-sand beaches, gentle surf carved by our kayak or the graceful underwater meandering of a green sea turtle, I’m inclined to yield the floor to an earlier Oahu visitor. Author Samuel L. Clemens had adopted the pen name Mark Twain just before he visited Hawaii in 1866, and years later wrote of “its garlanded crags, its leaping cascades, its plumy palms drowsing by the shore . . . in my nostrils still lives the breath of flowers that perished twenty years ago.”

Far from the madding crowd, we experienced Oahu’s spectacular beauty in, on and around the water.

'Fulfillment of joy'

On the roughly half-hour drive to Ko Olina from the airport, we made a quick stop at Pearl Harbor to visit the memorial and the USS Missouri, which is docked nearby. Together, they serve as bookends to World War II. It’s always humbling to visit the sunken USS Arizona to remember the 2,403 American lives lost on Dec. 7, 1941, and fascinating to then stand in the spot on the USS Missouri where Japan signed its surrender nearly four years later.


Then on to Ko Olina. Its name, which translates to “fulfillment of joy,” dates to when Hawaii’s royal family fished there. The development is clustered around four man-made lagoons ringed by white sand.

We had marveled at the location during a visit five years before, due in no small part to the magnificent Aulani, a Disney Resort & Spa. Opened in 2011, it features one of the world’s largest private collections of Hawaiian artwork.

“Everything here tells the story of Hawaii,” said Manako Tanaka, who is the current “Aulani Ambassador,” a staff member who serves as a cultural envoy to the guests. Disney characters hang around the place, but, like the Mickey Mouse icons cleverly hidden in the wallpaper, require some effort to find — and the resort’s Hawaiian storytelling doesn’t revolve around a road trip with Goofy. Instead, as Tanaka described, it’s found in events such as an evening luau that traces how sugar interests cleared the land, and how Portuguese plantation workers introduced a funny little four-stringed instrument that the Hawaiians called a ukulele.


Or it’s found in astronomer Greg McCartney taking us on a tour of the night sky via two beachside telescopes, from twinkling Canopus to sparkling Sirius to Hoku-lei (Capella), the brightest in a circle of five stars that owes its Hawaiian name to hoku (star) and lei (wreath).

Aulani’s neighbor, and the newest addition to the development, is the sumptuous Four Seasons Resort Oahu at Ko Olina. It opened in June 2016 after an 18-month makeover of the former J.W. Marriott Ihilani, and served as our base for two days of exploration.

My wife, Mica, and I arose before dawn our first morning to start a 45-minute drive north along Route 93 past the hardscrabble communities of Waianae and Makaha.


The roadway peters out into a muddy, lumpy, impassable road. From there, we began the 2½-mile hike to our day’s objective: Kaena Point State Park, the island’s western tip, and a place that according to Hawaiian custom signifies the “leaping place of souls,” a sacred spot where mortals can rejoin their ancestors in the afterlife.


We stayed tethered to terra firma, but the coastal scenery — black volcanic arches, bleached-white coral deposits, verdant hillsides — lent the place a spiritual quality. Wildlife abounds: red-crested cardinals, monarch butterflies, Laysan albatrosses riding air currents.

The ocean never feels very far away, even at dinnertime, when locally caught seafood steals the show. We trolled through platters of pink snapper and shrimp and noodles at Mina’s Fish House one night, and followed up the next night with mahi mahi, a curried fish stew and lobster-topped deviled eggs at Monkeypod Kitchen.


Our last morning in Ko Olina found my son, David, 21, and me aboard the Office, a 32-foot scuba charter operated by Nani Kai Dive Adventures & Academy. Matthew Lipscomb, the dive instructor, cautioned us about two outfall pipes that send warm water from an electric power plant into the ocean.


“You can go over the flow, or under it — you just don’t want to be in the middle,” he said. “It can push you a quarter-mile out to sea.”

With that warning prominently in mind, we steered clear of the pipes but stayed close to the plentiful tropical fish. A green sea turtle, friendly or unafraid or both, kept us company, effortlessly gliding through the water.

Personalizing the waves

Certain constants come to mind in relation to Oahu’s North Shore. Surfing, for starters. Shrimp trucks. Shave ice in quaint Haleiwa. We stopped for the latter two essentials, and for some local insight into surf conditions as a precursor to a planned stand-up paddleboard outing.


“Watch out for the currents,” cautioned Vince Wells, manager of T&C Surf Designs.

Similarly, Heidi Burgoyne, whose gear-rental service would supply my paddleboard, warned against strong winds.


Now, before we get to the part where I dismissed all this perfectly good advice, in my defense I had not yet seen the North Shore roadside markers where extremely experienced surfers encountered their last wave. Nor had I met the surfer walking back to the pullout for Kapaeloa Beach, the forlorn halves of his surfboard tucked under each arm.

“I break one just about every year,” he told me.

With that established, let’s just say I would have been better off not taking my paddleboard into the 6-foot-high waves taunting me from the beachside house we rented northeast of Haleiwa. They won Round 1, but I remained intent on a rematch the next morning, this time on a surfboard, with a little help from new friends.


Center, balance, patience — this was the counsel from surf instructors Noah Manning and Nate Fletcher of Hans Hedemann Surf School. They drove us to Kawela Bay, a sheltered spot with waves about half as high as those I’d tackled the day before.


Both my son and daughter Sophia, 12, were up on their boards quickly and coasting toward shore. I managed to stand for about two seconds on one pass — score that as a victory — and on my final try Fletcher promised that the incoming wave had my name on it.

I paddled hard, stayed centered and balanced, did a three count and . . . concluded that my Hawaiian name must translate to “Wipeout.”

Windward side and beyond

Hands-down, the day-long drive from the North Shore around the island’s windward side stole the show as far as unspoiled natural coastal beauty. From tiny Kahuku south to bustling Kaneohe, Route 83 (the Kamehameha Highway, named for the king who unified the islands) hugs the shoreline for long, deserted stretches.


Then, from endearing Kailua around the southeastern tip to the urban fringes of Honolulu, Route 72 winds past stunning views of Makapuu Beach and the twisted lava formations around the Halona Blowhole. Just past the turn to Hanauma Bay (an ideal snorkeling spot), civilization intrudes again.


We broke up the drive with stops for morning mountain biking at Kualoa Ranch Private Nature Reserve, lunch, and kayaking in Kailua Beach Park’s calm surf.

Our last night was spent at the foot of Hawaii’s most recognizable feature, the serrated green ridgeline of Diamond Head State Monument. Most visitors see it from the northwest, in Waikiki, but we were on the east side at the Kahala Hotel & Resort, an elegant oasis with the added benefit of a dolphin lagoon. That allowed us to get face-to-face one morning with a 10-year-old Atlantic bottlenose dolphin named Hua.

Later, we began the hour-long switchback trek up the Diamond Head Summit Trail. The massive volcanic cone had served as a barrier between us and Waikiki, but when we reached the top, the long beach and its attendant high-rises swallowed the view.


Twain, standing on just such a spot, described how “the distant lights of Honolulu glinted like an encampment of fireflies.”

The city’s population then numbered roughly 15,000 — a far cry from today’s roughly 400,000. I don’t know what barbs he might aim at ultra-busy Waikiki, but I’d like to think that if he had circumnavigated the rest of Oahu with us he would still hold these words to be true today:

“There they lie, the divine islands, forever shining in the sun, forever smiling out on the sparkling sea . . . and whosoever looks upon them once will never more get the picture out of his memory till he die.”

Pulaski is a writer based in Portland, Ore.

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If you go

Where to stay

Four Seasons Resort Oahu
at Ko Olina

92-1001 Olani St., Kapolei


Exactly what you expect from Four Seasons — casual elegance, and everything just right. New owners spent a reported $500 million to acquire and renovate the former J.W. Marriott Ihilani, including the addition of a breathtaking infinity pool with sunset views. Rooms from $589.

Aulani, a Disney Resort & Spa

92-1185 Aliinui Dr., Kapolei


A huge hit since its 2011 opening, this resort has everything a kid could want — waterslides, a lazy river and opportunities to interact with Disney characters. But it’s the Hawaiian artwork and cultural references — not Mickey Mouse — that steal the show. Rooms from $484.

The Kahala Hotel & Resort

5000 Kahala Ave., Honolulu


Just around the corner from Waikiki but feeling like a world away, this timeless resort has welcomed presidents and other celebrities by the scores. For good reason: old world elegance in the rooms and public spaces, and impeccable service to match. Rooms from $362.

Where to eat

La Hiki Kitchen (at the Four Seasons)

92-1001 Olani St., Kapolei


A breakfast buffet with countless possibilities, plus casual, locally sourced dinner fare like beer-can-roasted chicken and husk-roasted corn. Appetizers from $11, main dishes from $23.

Mina’s Fish House (at the Four Seasons)

92-1001 Olani St., Kapolei


Picture flawless service, a terrace setting under tiki torches and stars, and a local fisherman unveiling the catch of the day; we went for the fried opakapaka (pink snapper), with garlic-fried rice. The Kona lobster and coconut bisque is amazing, as is the butter-soft ahi tartare. Appetizers from $16, main dishes from $37.

Monkeypod Kitchen

92-1048 Olani St., Suite 4-107, Kapolei


This fun and casual spot from chef Peter Merriman excels in so many ways, but notably in beginnings (inventive tropical drinks) and endings (pie, from strawberry to coconut). In between await wood-roasted chicken wings, lobster-topped deviled eggs and fish selections caught that morning. Appetizers from $8, main dishes from $15.

Island Vintage Coffee

92-1048 Olani St., Suite 3-103C, Kapolei


We came here expecting just a coffee place and instead found artfully crafted breakfast plates, garnished with tropical flowers and fresh fruit. Breakfast plates start at $10, sandwiches at $12.

Uncle Bo’s Pupu Bar & Grill

66-111 Kamehameha Hwy., Unit 101, Haleiwa


Sleepy Haleiwa isn’t really known for its hip dinner spots, but one bite of its seafood trap (a medley of fresh fish, calamari and shrimp swimming in a chili and garlic oyster sauce) will shift your perspective. The hamachi sashimi I had was fresh and tender. End your meal with a warmed fudge brownie and ice cream. Appetizers from $8, main dishes from $17.

Moke’s Bread & Breakfast

27 Hoolai St., Kailua


Fresh, inexpensive and satisfying breakfast is what Moke’s is all about. Don’t miss the Lilikoi pancakes, which are topped with their yellow passion-fruit cream sauce. Full breakfast dishes start at $9.

Plumeria Beach House (at the Kahala)

5000 Kahala Ave., Honolulu


From fresh fish to the signature Loco Moco — braised short ribs over steamed rice — this casual eatery is open morning to night. Notable dishes include their expansive breakfast buffet and curry lunch buffet (Wednesdays only). Appetizers from $13, main dishes from $16.

What to do

Pearl Harbor Historic Sites

11 Arizona Memorial Dr., Honolulu


Quietly moving and always worth a trip to remember the lives lost here. Although the USS Arizona Memorial is temporarily closed because of structural concerns, and will remain so “for an undetermined period of time while repairs are made,” the visitors center and other historical sites are open. Because of the memorial closure, visitors can instead take a 15-minute narrated harbor tour of Battleship Row and around the memorial. There is no cost for this short harbor tour or a visit to the memorial when it reopens, but timed reservations must be made at for a small service fee. The National Park Service also typically hands out 1,300 tickets daily on a first-come basis. Tickets to related sites such as the USS Missouri are additional; a passport for all is $72.

Nani Kai Dive Adventures & Academy

92-100 Waipahe Pl., Ko Olina


Friendly, knowledgeable and convenient — the location at Ko Olina Marina means divers are at sites such as Electric Beach in mere minutes. A two-dive charter runs $199 per person; guests or snorkelers cost $130 each.

Hans Hedemann Surf School

57-091 Kamehameha Hwy., Kahuku


Easy waves combined with friendly and patient instructors make for a couple of hours of fun and — keep your fingers crossed — a good shot at first-time success. They have locations in Waikiki and North Shore. A two-hour small-group surf lesson is $100 a person.

Waimea Valley

59-864 Kamehameha Hwy., Haleiwa


The lush valley features flora from around the world and a scenic waterfall. Entrance is $16.95 for adults.

Kualoa Ranch Private Nature Reserve

49-560 Kamehameha Hwy., Kaneohe


This ranch-turned-movie-site offers tours and activities ranging from horseback rides to zip lines. The electric mountain bike tour we chose cost about $130, plus tax and transportation if needed.

Dolphin Quest (at the Kahala)

5000 Kahala Ave., Honolulu


Get up close and personal (hugs and kisses included) with Hua and other dolphins in the Kahala’s lagoons. Rates start at $149.

Diamond Head Summit Trail

Diamond Head State Monument, between Makapuu Avenue and
18th Avenue, Honolulu


The winding hour-or-so walk to the top of this 0.8-mile trail (one-way) rewards visitors with stunning views, especially north to Waikiki. Entry fee $5 per vehicle.

Hanauma Bay Nature Preserve

7455 Kalanianaole Hwy., Honolulu


Incredible snorkeling and a lovely beach, but it gets crowded, especially on weekends. Entry fee is $7.50 for adults; shuttle, lockers, gear are extra. Closed Tuesdays.

Rainbow Watersports

Haleiwa Beach Park, Haleiwa


For a nominal fee, you can get delivery (and pick up) of a paddleboard or kayak to and from your North Shore doorstep. Rentals start at $20 per hour.