Here's How to Take a Road Trip on O‘ahu’s Southeastern Coast - Hawaii Magazine (2024)

The early morning sun streaks through monkeypod trees as my wife, Kaila, and I walk the aisles of the Kapi‘olani Community College Farmers Market, run by the Hawai‘i Farm Bureau. Here, dozens of local farms and businesses sell their produce and products every week. And, it turns out, it’s also the perfect starting point for our road trip along O‘ahu’s southeastern coast.

The air is warm and the sky blue as we chow down on our hastily chosen picks from the market: a seared ‘ahi steak plate lunch from Hawaiian Style Chili and from Island Banana Juice, a smoothie made entirely from Hawai‘i-grown bananas. From here, along the foothills of Lē‘ahi, better-known to the outside world as Diamond Head, we’ll make our way to Kalaniana‘ole Highway, with the Makapu‘u Lighthouse as our destination. I’m relatively unfamiliar with this side of the island, and I’m excited to explore it. It’s home to sleepy coastal communities and, among other things, magnificent Maunalua Bay, according to mo‘olelo (stories), a landing spot for some of the earliest Polynesian voyagers to Hawai‘i.

As we drive east through Wai‘alae and Kāhala, the small residential homes surrounding Kapi‘olani Community College are replaced with bigger, posher places. We drive past The Kāhala Hotel and Resortthe same way visitors to Los Angeles might drive past the Beverly Hills Hotel, pointing at its grand entryway and admiring its boutique luxury appeal. Opened in 1964, the resort fronts gorgeous Kāhala Beach. It’s the perfect place to stay if you’re looking to be near Waikīkī without being in Waikīkī.

Entering the east side’s main thoroughfare, where the bustling H-1 Freeway becomes Kalaniana‘ole Highway, we drive past the residential neighborhoods of Wai‘alae Iki, ‘Āina Haina and Niu Valley. On our left, mauka (toward the mountains), residential roads wind up dry hills, and on our right, makai (toward the ocean), are beachfront homes and gated communities with dead-end streets that lead to hidden beach-access paths known only to those familiar with the area.

Still feeling ​​peckish, I make a pitstop at the ‘Āina Haina Shopping Center, where a surprisingly large amount of great food options await. Uncle Clay’s House of Pure Aloha serves ​shave​ ice made using artisanal syrups with locally sourced ingredients. But I’m not ​craving​​ something sweet. While Foodland Farms’ collection of grab-and-go bentos is the obvious option, I’m all about trying new things today and find myself ch​o​​​wing down on a vegan taco from Lē‘ahi Health. The bacon mustard taco ($11) is not what it seems—​​replace the bacon with a mix of kale, veggies, corn, black beans and coconut bacon, and the taco with a warm slice of pita bread topped with almonds—but it sure is delicious. Better yet, I actually feel better after eating it, with the fresh, healthy ingredients hitting all of my nutritional goals. With a pep in my step, we’re once again on the move.

A few miles down the highway and we finally emerge in Hawai‘i Kai, where the next stop on our journey awaits.

Past Hawai‘i Kai​,​ Kalaniana‘ole Highway straddles a stretch of sharp, rocky coastline that’s a sight to see. As we skirt around Koko Crater, we’re sandwiched between jagged lava rock outcroppings and the big blue Pacific. It’s not a bad place to be, but we drive on, past numerous scenic lookouts. We’re headed for the most scenic of them all—the lookout atop Hālona Beach Cove.

I’ve never been to Hālona Beach Cove myself, nor had I ever seen the equally famous Hālona Blowhole in action. But after standing at the lookout and watching the sun highlight the electric blue waters of the secluded beach below—the same beach that Burt Lancaster and Deborah Kerr frolicked on in the classic 1953 flick “From Here to Eternity”—I can understand why the cove is so revered. As waves rush into the cove, I head over to the blowhole and watch as ocean water erupts from a puka (hole) in the rocks. The blast carries 30 feet into the air, accompanied by the whooping and hollering of fellow spectators.

Just down the road, Sandy Beach’s ​whomping​ shorebreak entices us, but since our once blue skies have given way to gray clouds and intermittent showers, we opt to continue down to nearby Koko Crater Botanical Garden. As we enter the 60-acre city-run garden, located inside an old volcano crater, we’re greeted by a grove of plumeria trees, torrential rainfall and more kōlea, which migrate to Hawai‘i to escape the cold winters of Siberia and Alaska.

Moving through the garden’s collection of trees, flowers and other plants from around the world, Kaila and I quickly agree: This is the highlight of our trip. From the massive cacti in the cactus garden to the pear-shaped baobab trees in the Africa garden, we’re astonished by the otherworldly flora. Despite the rain—and our very muddy shoes—we take our time here.

But we eventually ​leave​, headed for the Makapu‘u Point Lighthouse Trail. Perfect for families or individuals who just don’t want to work that hard on a hike—yes, that’s me—this paved walkway rises gradually to a scenic lookout with magnificent views of the southeast coast. As I stare out at the ocean, I spot a few honu (Hawaiian green sea turtles) bobbing in the water below, and nearby the iconic red-roofed Makapu‘u Lighthouse. Looking around some more, I ​spot​ my wife. And combined with everything else I’ve seen, I realize what I’ve really been looking at since we left Lē‘ahi: the perfect Hawaiian day.

This story was originally published in our Summer 2024 issue, which you can buyhere. Better yet,subscribeand get HAWAIʻI Magazine delivered to right to your mailbox.