Oahu, the Hawaiian island that is home to Honolulu, the state’s capital, can seem urban to the core. But Oahu is so much more than its bustling, modern South Shore — and there’s no better way to discover its slower-paced charms than by “going holoholo,” a vintage Hawaiian-English phrase that has come to mean taking a pleasure drive.
On Oahu, locals go holoholo with a drive around the island, stopping along the way to see the sights, breathe the sea air and smell the fragrant plumeria.
Here’s a rewarding round-the-island itinerary, starting in Waikiki. Long stops will alter your timetable, but there are so many memorable places to linger that we’ve highlighted some of our favorites.
Savor a morning meal at Waikiki’s Hau Tree Lanai, an open-air terrace beneath the flowering trees that once sheltered Victorian author Robert Louis Stevenson as he lounged with Hawaiian royalty. Then, hop on the only interstate highway system in the U.S. that doesn’t cross a single state line, and head west on H-1. Near Pearl Harbor, swing north onto H-2 and watch the concrete jungle give way to green fields.
When the spiky crowns of pineapple appear, you’re getting close to Dole Plantation, which celebrates Oahu’s rich agricultural heritage with a pineapple train ride, a pineapple garden, an excellent gift shop and restaurant, and more.
Beyond the plantation, Oahu’s fabled North Shore appears on the horizon. Descend to Haleiwa, the surf town whose must-stop is Matsumoto Shave Ice, an island institution since 1951. Matsumoto’s serves the classic Hawaiian treat with dozens of refreshing flavors such as mango, coconut and the citrus-like yuzu. Order your favorite combo and add a scoop of ice cream. Trust us.
Haleiwa is the gateway to the North Shore, a string of world-famous beaches and surf breaks, such as the Banzai Pipeline, that helped the Hawaiian-born sport go global. A formerly lesser-known beach, Laniakea (Lah-nee-AH-kay-a), has been adopted by endangered green sea turtles that like to bask on the beach.
Next up: Waimea. The colossal winter surf of picture-perfect Waimea Bay gave rise to the legendary Eddie Aikau big-wave surfing tournament, which takes place when waves reach at least 20 feet high (only nine times in 38 years). Across the street is Waimea Valley, one of Oahu’s most immersive and accessible Native Hawaiian environments. Once home to the island’s high priests, the valley became a botanical garden in the 20th century. Today, a paved, shady two-mile walk weaves through cultural sites, interactive demonstrations (lei making, weapon making, wood carving) and exhibits to the island’s only lifeguarded, swimmable waterfall area. If the walk seems too far, you can hop on a shuttle.
Round the island’s north point and stop for lunch at Kahuku Farms Cafe, a charming, friendly outdoor venue that transforms the farm’s tropical bounty into refreshing drinks and hearty sandwiches and pizzas. Don’t skip the lilikoi cooler, made with the sweet-tart yellow passionfruit. Farm tours are also available. If vegetarian fare isn’t your thing, save yourself for Pounders Restaurant farther on in the town of Laie (Lah-EE-ay), which serves up farm-fresh produce, island-raised grass-fed beef and locally caught fish.
Laie is adjacent to the Polynesian Cultural Center, a pan-Pacific cultural theme park (think fire knife dancers, hulas and canoe rides) that is well worth taking the rest of the afternoon to enjoy, especially if you have the grandkids in tow. If you save the cultural center for another day, the onward drive along Oahu’s east shore turns into a lazy shoreline cruise between vivid blue waters and the lush green Koolau Mountains. There’s a constant stream of lovely, uncrowded beaches at which to pause and stretch your legs, and a series of offshore islands that have a place in Hawaiian legend and lore, such as Mokolii (also called Chinaman’s Hat).
Along the way, you may pass roadside stands selling homemade dried aku (fish), pickled mango, lychee, starfruit and other seasonal treats you won’t find in a supermarket. In a gorgeous wooded setting at the foot of the Koolau Mountains, the Byodo-In Temple is a scaled-down replica of the famous temple in Uji, in the Kyoto Prefecture of Japan. Feed the colorful koi or ring the three-ton brass peace bell for good luck.
From there, you have two choices. If you’re ready to roll home, cross the Koolau Mountains on the spectacular Pali Highway, pausing at the Pali Lookout, the site of an important 18th-century inter-island battle. From the lookout, you can survey Oahu’s magnificent east shore (where you’ve just been), an emerald carpet unfurling to the Pacific, then make the short drive back to Honolulu.
If there’s still gas left in the tank, skip the Pali and head on Highway 72 toward Waimanalo. You’ll be passing by popular beaches — Kailua, Lanikai, Waimanalo — that are considered among the world’s best. Rounding the island’s southeastern tip, enter the arid Kaiwi coast, with dramatic ocean views at every turn. At the Halona Blowhole, watch waves fountain up to 30 feet high through a narrow lava tube, reminiscent of a whale’s spout. From December through March, humpback whales visit, too; you might see a real spout, a tail or even a playful breach.
For dinner, go upscale at celeb chef Roy Yamaguchi’s flagship Roy’s Restaurant in Hawaii Kai. Enjoy dazzling Pacific Rim cuisine along with the ocean view. Or do as the kamaainas (longtime residents) and enjoy a waterfront meal at the Koko Marina location of Hawaii’s favorite casual diner, Zippy’s. Then head back to home base, as the sun sinks into the sea.
Editor's note: This article was originally published on April 18, 2018. It's been updated to reflect new information.