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Urban Honolulu, with its history, cuisine, and shopping, can captivate travelers for days. But the rest of the island draws them out in its promise of wild coastlines and unique adventures.

Oahu’s Southeast Coast

From the high-rises of Waikiki, venture down Kalakaua Avenue through tree-lined Kapiolani Park to take a look at a different side of Oahu, the arid southeast shore. The landscape here is more moonscape, with prickly cacti onshore and, in winter, spouting whales cavorting in the water.

To get to this coast, follow Kalakaua Avenue past the multitiered Dillingham Fountain and around the bend in the road, which now becomes Poni Moi Road. Make a right on Diamond Head Road and begin the climb up the side of the old crater. At the top are several lookout points, so if the official Diamond Head Lookout is jammed with cars, try one of the other lookouts just down the road. The view of the rolling waves and surfers is spectacular; take the time to pull over. This is also a wonderful place to begin your day early and watch the sun rise.

Diamond Head Road rolls downhill into the ritzy community of Kahala. At the fork in the road at the triangular Fort Ruger Park, veer to your right and continue on the palm tree–lined Kahala Avenue. Make a left on Hunakai Street, and then take a right on Kīlauea Avenue and look for the sign, “H-1 west.” Turn right at the sign, although you won’t get on the H-1 freeway; instead, get on Kalanianaole Highway, a four-lane highway interrupted every few blocks by a stoplight. This is the suburban bedroom community to Honolulu, marked by malls on the left and beach parks on the right.

One of these parks is Hanauma Bay ★★; you’ll see the turnoff on the right when you’re about half an hour from Waikiki. This marine preserve is one of the island’s best places to snorkel; you’ll find the friendliest fish on the island here. A reminder: The beach park is closed on Tuesday.

Around mile marker 11, the jagged lava coast itself spouts sea foam at the Halona Blowhole. Look out to sea from Halona over Sandy Beach and across the 26-mile gulf to neighboring Molokai and the faint triangular shadow of Lanai on the far horizon. Sandy Beach ★ is one of Oahu’s most dangerous beaches, with thundering shorebreak. Bodyboarders just love it.

The coast looks raw and empty along this stretch as the road weaves past old Hawaiian fish ponds and the famous formation known as Pele’s Chair, just off Kalanianaole Highway (Hwy. 72) above Queen’s Beach. From a distance, the lava-rock outcropping looks like a mighty throne; it’s believed to be the fire goddess’s last resting place on Oahu before she flew off to continue her work on other islands.

Ahead lies 647-foot-high Makapuu Point, with a lighthouse that once signaled safe passage for steamship passengers arriving from San Francisco. The automated light now brightens Oahu’s south coast for passing tankers, fishing boats, and sailors. You can take a short hike up the Makapuu Lighthouse Trail ★★ for a spectacular vista.

Turn the corner at Makapuu and you’re on Oahu’s windward side, where cooling trade winds propel windsurfers across turquoise bays; the waves at Makapuu Beach Park ★ are perfect for bodysurfing.

Ahead, the coastal vista is a profusion of fluted green mountains and strange peaks, edged by golden beaches and the blue, blue Pacific. The 3,000-foot-high, sheer, green Koolau mountains plunge almost straight down, presenting an irresistible jumping-off spot for paragliders. Most likely, you’ll spot their colorful chutes in the sky, looking like balloons released into the wind.

Winding up the coast, Kalanianaʻole Highway (Hwy. 72) leads through rural Waimanalo, a country beach town of nurseries and stables. Nearly 4 miles long, Waimanalo Beach ★★ is Oahu’s longest beach and popular with local families on weekends. Take a swim here or head on to Kailua Beach ★★★, one of Hawaii’s best.

The Windward Coast

From the Nuunau Pali Lookout ★, near the summit of the Pali Highway (Hwy. 61), you get the first hint of the other side of Oahu, a region so green and lovely that it could be an island sibling of Tahiti. With its many beaches and bays, the scenic 30-mile Windward Coast parallels the corduroy-ridged, nearly perpendicular cliffs of the Koolau Range, which separates the windward side of the island from Honolulu and the rest of Oahu. As you descend on the serpentine Pali Highway beneath often-gushing waterfalls, you’ll see the nearly 1,000-foot spike of Olomana, a bold pinnacle that beckons intrepid hikers, and, beyond, the town of Waimanalo, where many of Native Hawaiian descent live. Stop by Ai Love Nalo ★, for a fruit smoothie or fresh and flavorful renditions of local classics, such as a veggie laulau or poi parfait, layered with seasonal fruit, granola, and coconut flakes.

From the Pali Highway, to the right is Kailua, Hawaii’s biggest beach town, with more than 50,000 residents and 2 special beaches, Kailua Beach ★★★ and Lanikai Beach ★★★. You can easily spend an entire day in Kailua, which I absolutely recommend, whether to laze on the sand or stand-up paddle to the Mokuloa Islands. But Kailua isn’t all beach: Chic boutiques line the streets, such as Oliver Men’s Shop and the Aloha Beach Club, and you can grab a shave ice at The Local Hawaii.

After whiling away a day in Kailua, allocate another day for exploring the rest of the Windward coast. Take Highway 830N, which goes through Kaneohe and then follows the coast to Heeia State Park. Here, you’ll find Heeia Fish Pond, which ancient Hawaiians built by enclosing natural bays with rocks to trap fish on the incoming tide. The 88-acre fish pond, which is made of lava rock and had four watchtowers to observe fish movement and several sluice gates along the 5,000-foot-long wall, is now in the process of being restored.

Drive onto Heeia Pier, which juts onto Kaneohe Bay. You can take a snorkel cruise here or sail out to a sandbar in the middle of the bay for an incredible view of Oahu that most people, even those who live here, never see. Incredibly scenic Kaneohe Bay is spiked with islets and lined with gold-sand beach parks like Kualoa Regional Park ★, a favorite picnic spot. The bay has a barrier reef and four tiny islets, one of which is known as Moku o loe, or Coconut Island. Don’t be surprised if it looks familiar—it appeared in Gilligan’s Island.

Everyone calls the other distinctively shaped island Chinaman’s Hat, but it’s really named Mokolii. It’s a sacred puu honua, or place of refuge, like the restored Puu Honua Honaunau on the Big Island of Hawaii. Excavations have unearthed evidence that this area was the home of ancient alii (royalty). Early Hawaiians believed that Mokolii (Fin of the Lizard) is all that remains of a mo‘o, or lizard, slain by Pele’s sister, Hiiaka, and hurled into the sea. At low tide you can swim out to the island, but keep watch on the changing tide, which can sweep you out to sea. You can also kayak to the island; park your car and launch your kayak from Kualoa Regional Park. It’s about a half-hour hike to the top, which awards you views of the Koolau mountains and Kaneohe Bay.

Little poly-voweled beach towns like Kahaluu, Kaaawa, Punaluu, and Hauula pop up along the coast, offering passersby shell shops and art galleries to explore. Roadside fruit and flower stands vend ice-cold coconuts to drink (vendors lop off the top and provide the straws) and tree-ripened mangoes, papayas, and apple bananas (short bananas with a tart apple aftertaste).

Sugar, once the sole industry of this region, is gone. But Kahuku, the former sugar-plantation town, has found new life as a small aquaculture community with shrimp farms. Not of all the shrimp trucks use local shrimp, however—Romy’s is one of the few, while the perpetually popular Giovanni’s cooks up imported, frozen shrimp. Definitely stop for a poke bowl at Kahuku Superette.

From here, continue along Kamehameha Highway (Hwy. 83) to the North Shore.

Hawaii’s general stores

The windward side harbors some of Oahu’s best remaining general stores—Hawaii’s mom-and-pop version of a convenience store or a New York bodega. Here, nostalgia is sold alongside the boiled peanuts by the cash register. Under the same roof, you might find smoked meat and toilet paper, butter mochi and fishing supplies. Here are three of our favorites (listed from south to north):

Waikane Store, 48-377 Kamehameha Hwy. (808/239-8522): Locals pop into this little lime-green store that dates back to 1898. Nothing fancy here, just simple maki sushi rolls wrapped in wax paper, fried chicken, and homemade cookies—all perfect for the beach.

Ching’s Punaluu Store, 53-360 Kamehameha Hwy. (808/237-7017): This bright-red store, run by the third generation, offers all the local favorites—from chili to soft serve. Don’t miss the butter mochi—a local sweet treat made with glutinous rice flour. It’s pure, chewy comfort.

Kahuku Superette ★★★, 56-505 Kamehameha Hwy. (808/293-9878): Kahuku’s shrimp trucks may entice with their potent, garlicky smells, but absolutely don’t miss the poke (seasoned raw fish) from Kahuku Superette. If you’re not afraid of kimchi, get the special poke: fresh ahi tuna with a housemade, fermented, gingery paste that’s sure to waken your taste buds. Want something milder? Try the shoyu poke. This nondescript store is a must-stop for many of Honolulu’s notable chefs.

Central Oahu & the North Shore

If you can afford the splurge, rent a convertible—the perfect car for Oahu to enjoy the sun and soaring views—and head for the North Shore and Hawaii’s surf city: Haleiwa ★★★, a former sugar-plantation town and a designated historic site. Although in recent years, Haleiwa has been spruced up—even the half-century old, formerly dusty Matsumoto’s Shave Ice has new digs now—it still maintains a surfer/hippie vibe around the edges. For more, see “Surf City: Haleiwa” below.

Getting there is half the fun. You have two choices: The first is to meander north along the lush Windward Coast, following the coastline lined with roadside stands selling mangoes, bright tropical pareu, fresh corn, and pond-raised prawns. Attractions along that route are discussed in the previous section.

The second choice is to cruise up the H-2 through Oahu’s broad and fertile central valley, past Pearl Harbor and the Schofield Barracks of From Here to Eternity fame, and on through the red-earthed heart of the island, where pineapple and sugarcane fields stretch from the Koolau to the Waianae mountains, until the sea reappears on the horizon.

Once you’re on H-1, stay to the right side; the freeway tends to divide abruptly. Keep following the signs for the H-1 (it separates off to Hwy. 78 at the airport and reunites later on; either way will get you there), and then the H-1/H-2. Leave the H-1 where the two highways divide; take the H-2 up the middle of the island, heading north toward the town of Wahiawa. That’s what the sign will say—not North Shore or Haleiwa, but Wahiawa.

The H-2 runs out and becomes a two-lane country road about 18 miles outside downtown Honolulu, near Schofield Barracks. The highway becomes Kamehameha Highway (Hwy. 99 and later Hwy. 83) at Wahiawa. Just past Wahiawa, about a half-hour out of Honolulu, the Dole Pineapple Plantation, 64-1550 Kamehameha Hwy. (www.dole-plantation.com; 808/621-8408; daily 9:30am–5pm; bus: 52), offers a rest stop, with pineapples, pineapple history, pineapple trinkets, pineapple juice, and pineapple soft serve. This agricultural exhibit/retail area features a train ride and maze that kids will love to wander through; it’s open daily from 9:30am to 5pm (activities start at $6 adults, $5.25 children 4–12).

“Kam” Highway, as everyone calls it, will be your road for most of the rest of the trip to Haleiwa, on the North Shore.

Central Oahu Attractions

On the central plains of Oahu, tract homes and malls with factory-outlet stores are now spreading across abandoned sugarcane fields. Hawaiian chiefs once sent commoners into thick sandalwood forests to cut down trees, which were then sold to China traders for small fortunes.

Surf City: haleiwa

Only 28 miles from Waikiki is Haleiwa ★★★, the funky former sugar-plantation town that’s now the world capital of big-wave surfing. Haleiwa comes alive in winter, when the waves rise; then, it seems, every surfer in the world is here to see and be seen.

Officially designated a historic cultural and scenic district, this beach town was founded by sugar baron Benjamin Dillingham, who built a 30-mile railroad to link his Honolulu and North Shore plantations in 1899. He opened a Victorian hotel overlooking Kaiaka Bay and named it Haleiwa, or “house of the ʻiwa,” the tropical seabird often seen here. The hotel and railroad are gone, but the town of Haleiwa, which was rediscovered in the late 1960s by hippies, manages to hold onto some of its rustic charm. Of course, like other places on Oahu, that is changing; some of the older wooden storefronts are being redeveloped and local chains such as T&C Surf are moving in. Arts and crafts, boutiques, and burger joints line both sides of the town. There’s also a busy fishing harbor full of charter boats and captains who hunt the Kauai Channel daily for tuna, mahimahi, and marlin.

Just down the road are the fabled shrines of surfing—Waimea Beach, Banzai Pipeline, Sunset Beach—where some of the world’s largest waves, reaching 20 feet and higher, rise up between November and January. November to December is the holding period for Vans Triple Crown of Surfing (http://vanstriplecrownofsurfing.com), one of the world’s premier surf competition series, when professional surfers from around the world descend on the 7-mile miracle of waves. Hang around Haleiwa and the North Shore and you’re bound to run into a few of the pros. Battle the traffic to come up on competition days (it seems like everyone ditches work and heads north on these days): It’s one of Oahu’s best shows. For details on North Shore beaches. 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.