Oahu, Hawaii: Insider’s Guide

The insider advice on this page is from two of Wendy’s Trusted Travel Experts for Hawaii: Jay and Dani Johnson of Coastline Travel.

Trusted Travel Expert

Jay and Dani Johnson

Jay and Dani spend six weeks a year in Hawaii, escorting groups of Silicon Valley execs as well as vacationing with their two daughters. Their agency sends so many travelers to Hawaii that it has significant clout with the five-star resorts—which translates into perks for their travelers—but they also book rental homes when that’s the smarter choice for the group. They can arrange anything from multi-generational family reunions to pull-out-all-the-stops honeymoons, from kite-boarding lessons on Maui to private guided hikes on Kauai, the Big Island, and Oahu’s North Shore. Living in Los Angeles and with offices throughout California, they can also orchestrate out-of-the-box itineraries in their own backyard. They can arrange for Los Angeles Angels tickets right behind home plate, V.I.P. access to Disneyland, a cooking lesson with the head chef at Napa’s Michelin-starred Meadowood resort, glamping among the redwoods—or all of the above in one quick, efficient trip.

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Expect trips orchestrated by Jay and Dani to have a 5-night minimum and start at $1,000 per day for two travelers in low season (triple that for Christmas/New Year's), with an additional $500 fee for trips planned less than 60 days ahead.

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Where to Stay and Eat

Best bang-for-your-buck hotel
Oahu hotels tend to be less expensive than those on other Hawaiian islands. If you stay at the Halepuna Waikiki by Halekulani, not only do you save a bundle, but you also have signing privileges at the Halekulani Hotel, which allow you to make (sought-after) dining reservations there. Some stays also include daily breakfast.

Best-value splurge hotels
The Four Seasons Ko Olina sits on a beautiful white-sand beach on Oahu’s west side. Most of its rooms have floor-to-ceiling windows opening onto lanais with a water view. This is an ideal base for visiting Oahu—away from the hustle and bustle of Waikiki but still close to the USS Arizona Memorial and the North Shore. Dani and Jay’s travelers receive a resort credit, a room upgrade, and complimentary full American breakfast.

The Ritz-Carlton Turtle Bay Resort isn’t over-the-top luxury, but the price is attractive, and it’s on the North Shore (known for its fantastic surfing), far from the mobs of people in Waikiki. You get an outer-island experience without the cost of additional airfare. Plus, Turtle Bay offers a wide range of activities available right on site: You can kayak with sea turtles, ride horses, play pickleball or tennis, hike, and much more without ever leaving the property.

Meal worth the splurge
Mugen at ESPACIO The Jewel of Waikiki. Recognized for its locally sourced, seasonally driven cuisine and extensive wine list, Mugen merges all the elements of an intimate and sophisticated romantic evening.

Restaurants the locals love
Locals prefer to dine on the North Shore, as it is much more affordable and laid-back than the Waikiki area. Join them for a food crawl among the well-known shrimp trucks along Kamehameha Highway; Jay and Dani’s favorite is Pupukea Grill—don’t miss the Volcano Roll. Also on the North Shore, Lei Lei’s at Turtle Bay is justly famous for its tuna melt sandwich. Haleiwa Beach House, with its airy dining room and gorgeous sunset views, is another favorite.

For dining in the Waikiki area, the hands-down choice is Fete in Chinatown for new American, family-style dining in a hip brasserie—think Oahu meets Brooklyn. In 2022, Chef Maii was named Best Chef for the Northwest and Pacific Region by the James Beard Foundation; she is the first Native Hawaiian woman to win a James Beard award.

Dish to try
The mahi-mahi burger at Kua’Aina in Haleiwa.

What to See and Do

Don’t miss
There is so much more to Oahu than Waikiki! The North Shore offers amazing hikes, snorkeling, and volunteer opportunities with the Malaya Hawai’i Program: Give back to the community through beach clean-ups, native tree planting, or quilting sessions while learning more about the islands and culture of the ancient Polynesians. You can also watch surfers take on the Pipeline’s famous waves and eat at one of the many shrimp trucks.

Make time for the hidden gems of Oahu’s North Shore. Photo: Shutterstock

The three-and-a-half-hour snorkel trip with Wild Side Specialty Tours. You’ll see spinner dolphins in their natural habitat, and in winter you may also spot nearby whales.

Iolani Palace is the home built by the last Hawaiian king in the late 19th century. Iolani had electricity a few years before the White House did. Spring for the extra ticket to see all the treasures—including the Crown Jewels—on display in the basement rooms, and the palace kitchen.

The National Park Service arranges tours of Pearl Harbor. Tickets are released online 56 days prior. Don’t miss the tour of the U.S.S. Missouri, during which you can see where the crew slept and ate, and how they lived. Many visitors combine Pearl Harbor with a visit to the Punchbowl, an ancient volcanic crater that is now a military cemetery. If you have kids with you, visit the compound’s Pacific Aviation Museum, which has a combat flight simulator that lets you pretend to be a World War II pilot.

Don’t bother
The luau at the Polynesian Culture Center; the show is staged and touristy and the food is average. If you are looking to understand more about Hawaii’s history and culture, go instead to the Bishop Museum. The superb docents there can share much about the artifacts and history of the Polynesian people.

Sunset cruises on Oahu tend to be very crowded. Watching the sunset from Waikiki, down near Kapiolani Park, is less expensive and just as magnificent. If you are staying on the North Shore, go to Turtle Bay to watch the sunset, cocktail in hand. If you prefer your sunset cocktails with a side of music, head to House Without a Key at the Halekulani Hotel in Waikiki.

Waikiki Beach. It’s so packed with people that there’s no room to move, and the crowds can truly ruin a beautiful day at the beach. Try Waiminalo Beach, on the windward side, instead of the crowded beaches in Waikiki and Kailua. It’s a great beach for body surfing—especially during the week when there’s no one there—and it’s tree-lined, so nice and shady.

Best for families
A day at Kualoa Ranch, where the land scenes for Jurassic Park were filmed. You can tour the working ranch by open-air school bus, ATV, or horseback. There’s also a petting zoo, zip line, plenty of places to hike and picnic, and a secluded beach with a volleyball net, kayaks, canoes, and standup paddle boards.

The Koolau mountain range, near Kualoa Ranch, was a backdrop for Jurassic Park. Photo: Shutterstock

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