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Explore Oahu's Best: A Guide to Stay, Shop, and Savor in Hawaii's Diverse Island Paradise | ICONIC LIFE

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Explore Oahu’s Best: A Guide to Stay, Shop, and Savor in Hawaii’s Diverse Island Paradise

Oahu, Hawaii hero image

Courtesy of Turtle Bay Resort

Hawaii’s most populous state is also its most captivating. These are a few of our favorite things to do in Oahu.

As a longtime and frequent visitor to Hawaii, I’ve enjoyed the hospitality of nearly every island. Yet it had been years since I explored Oahu. Preferring the lowkey vibe of Maui, the verdancy of Kauai, and the isolation of Lana’i, I eschewed the state’s capital home thinking it too frenetic and too developed. But a recent visit proved that this megalopolitan isle and mai tais do indeed mix, and the effect is mesmerizing. With the guidance of a few in-the-know locals, I traversed Waikiki’s south and north shores to uncover Oahu’s bests. Here are the findings:

Where to stay: 

Oahu Hawaii halekulani

Courtesy of Halekulani

Mention Halekulani to anyone who has ever stayed at the Waikiki mainstay, and the response is that of unadulterated affection, proving that Halekulani is more than an Oahu resort—it’s a feeling. Established more than 100 years ago as one of the first hospitality ventures on Oahu, Halekulani and its prime Waikiki location allow for unobstructed views of the Pacific and of Diamondhead. Nearly every elegantly appointed guest room and suite feature ocean-facing lanais poised towards the sea and overlooking the stunning swimming pool. And when Halekulani is at full capacity, neighboring Halepuna Waikiki by Halekulani is the next best thing. Located directly across the street, the award-winning Halepuna features a rooftop pool with reservable cabanas that also afford stunning ocean vistas.

Oahu Hawaii Ritz Carlton

Courtesy of The Ritz Carlton, Waikiki Beach

Newer to the Oahu hospitality scene is The Ritz-Carlton, Waikiki Beach and its two stunning, modern towers with rooms and suites that offer clear views not only of the ocean but also of the vivacity of Hawaii’s OG beach town. Unique is The Ritz-Carlton’s residential aspect—every room and suite features a full kitchen and washer/dryer—making it an ideal retreat for families or larger groups. Luxury focused and progressive, the resort features several sustainability-focused initiatives such as under-sink water purification systems accompanied by the gift of aluminum water bottles.

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Courtesy of Turtle Bay Resort

On Oahu’s wild and windswept other side—the North Shore—Turtle Bay Resort encompasses 1300 acres of prime, oceanfront turf, which it stewards and preserves with utmost care. Turtle Bay guests are invited to explore the organic acreage via foot, horseback, surfboard or bicycle (grab a complimentary cruiser from the resort’s fleet). 12 miles of trail lead to stunning vistas along secluded, beachfront bays. All of this adventure comes with a bit of luxury. Beautifully appointed rooms and suites are situated to take full advantage of sunrise or sunset views. Two large swimming pools feature ample chaise seating. Additional lounging options are found along the shore of Kuilima Cove where gentle waves invite snorkeling and body surfing. For privacy, pack towels and sunscreen and walk the trail to secluded Kawela Bay. 

Where to shop:

Waikiki’s Kalakaua Avenue offers luxury shopping at its best. Along the picturesque palm tree-lined street you’ll find Luxury Row featuring all the biggest names in designer goods: Chanel, Dior, Prada, YSL, Bottega Veneta and more. Most items are 10% off typical retail, and Hawaii’s 4% sales tax rate makes for an extra bargain. 

Oahu Hawaii aloha shirt

Photo by Fran Miller

In Hawaii, aloha shirts are de rigueur fashion for men. Find your perfect print at Avanti. Favored by Bruno Mars, Dwayne “The Rock” Johnson, and other stars, Avanti aloha shirts, with patterns from the 1930’s, 1940’s and the 1950’s, feature Hawaiian scenes, flowers and points of interest in original patterns, prints and bright tropical colors and styles.

No other brand has defined the world of women’s surfing as has Roxy, the hip purveyor of swim and surf wear. Shop for casual beach basics at two boutiques along Kalakaua Ave., where you’ll find inspiration in the colorful wall murals and promotional photos featuring world champion long board surfer and Oahu local Kelia “Sis” Moniz and her pals.

On the North Shore, the small town of Hale’iwa features a main street lined with t-shirt and household goods boutiques. Malibu Shirts carries quality t’s with vintage images, such as the Primo beer logo, Hawaii’s ICONIC beer brand. 

What to do:

Waikiki is nearly synonymous with surfing, so “when in Rome,” follow suit with a lesson from Moniz Family Surf. This renowned Hawaiian family of surf champions provides the best in surf instruction. Teaching along the same beach where they each first learned, the Moniz siblings (father and mother too!) will have you hanging ten in no time. 

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Allow yourself to be willingly humiliated while laughing ‘til you cry at Caricature Party. Stationed each evening in front of SKY Waikiki seafood restaurant, a pair of artists captures eager patrons in silly portraits that emphasize unflattering characteristics. Become a participatory victim, or simply watch the fun.

Courtesy of Tahiti Hernandez-Kemper

Adrenaline seekers will find a happy home at Uproar Fitness, where world champion big wave surfer Billy Kemper and his wife Tahiti Hernandez-Kemper lead uplifting, up-tempo workouts and aerobics classes that inspire. Join them on the North Shore for challenging sessions that combine strength training, mindfulness, and a lot of fun, as hinted by the shimmering disco ball that hangs from the fitness studio ceiling.

Where and what to eat and drink:

Courtesy of Istanbul Hawaii

Istanbul Hawaii, in Honolulu’s Ward Village, is one of the only Turkish & Mediterranean restaurants in the state. Combining traditional flavor and heritage, Chef Ahu Hettema and her mother Nili Yildirim, both Turkish natives, provide appreciative diners with flavorful dishes made with local and imported ingredients. The “Shish” are a crowd favorite: ribeye, lamb, or chicken served with Mediterranean salad, saffron rice, and tzatziki. Don’t miss the creatively crafted cocktails which alone are worth a visit. Try the Evil Eye, with Angel’s Envy bourbon, cardamom, Turkish date and orange blossom.

Kaimana Beach Hotel’s Hau Tree restaurant is perfectly situated to capture the best Hawaiian sunset views. Enjoy the dusky show under a leafy, twinkle-lit canopy while enjoying a glass of bubbly. When the vista is this special, the food could easily be an afterthought, but the dinner dishes are creative and delicious. Pupu standouts include an impressive crudité tray, chip & rainbow caviar, and burrata toast. The handmade pastas are a draw, as are the fresh salads, and the grilled lamb chops.   

Courtesy of UMI

Located within Halepuna’s gracious lobby is UMI by Vikram Garg, the creation of the Indian born, French trained, and Japanese inspired global restauranteur and chef innovator. Inspired by the ocean’s harvest, Garg has created a captivating, seafood centric menu, yet the foie gras gyoza and the prime ribeye both belong on anyone’s “best tastes ever” list. The private collection caviar is not to be missed, as are the selected wine pairings that perfectly enhance every dish. 

Stock photo for Oahu Hawaii story

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You’ll find what I think is the best mai tai on the island at Halekulani’s Earl’s at House Without A Key, the new pool-adjacent bar where lead mixologist Tuda Grehan has perfected the traditional Hawaiian cocktail. 

On the North Shore, Turtle Bay Resort’s Alaia restaurant features locally sourced items from the resort’s own 468-acre Kuilima Farm. Here, a simple Little Gem lettuce salad illustrates exactly how wonderful just-picked goodness can be. It goes without saying that along the Pacific, any seafood fare promises to be outstanding, but at Alaia, Kona Kampachi Sashimi and Hawaiian Ahi Poke reach new levels of deliciousness. Start your meal with a crafted cocktail; the “Don’t Touch the Turtles” vodka-based tipple (named for the mantra aimed at over-enthusiastic snorkelers) is fittingly served in a gleaming copper turtle. 

For something a bit more casual, Zippy’s can’t be beat. A Hawaiian institution founded in 1966, beloved Zippy’s serves-up soul-satisfying Hawaiian and American classics from pancakes and omelettes, to chili and chicken dishes. 

Frozen Icecream in Oahu, Hawaii

Fran Miller

Snack attacks call for Musubi, the wildly popular item made with a packed white rice base topped with meat or fish (SPAM is a particular fave), and wrapped with seaweed. (Don’t knock it ‘til you’ve tried it.). Founded by four locals, Banan is a no dairy, no sugar soft serve made exclusively from frozen bananas. Order this tasty treat with a variety of toppings; peanut butter is a particularly good match. Don’t miss the salted caramel croissant at Halekulani Bakery. This sweet, sticky, and flaky pastry is as Instagram-worthy as it is delicious, as is nearly every pastry featured within the exalted cafe. And no visit to Hawaii is complete with a shave ice. This iconic dessert is exactly what it’s named—ice, shaved from a block, flavored with a choice of syrups and other sweet ingredients. Waiola Shave Ice is routinely voted as Hawaii’s best. 

 

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