A woman stands on the roof of a shack with outstretched arms and a view of the ocean behind her.

Soaking up the views in Oahu. Photo courtesy of Elyse Butler.

Three Perfect Days: A Trip to Oahu

Sunny FitzgeraldNovember 23, 2020

Go forest bathing and visit Iolani Palace.
Hike Pillbox Trail and take a lei making class.
Go surfing and visit taro patch in Waialua.

Oahu is known as The Gathering Place, and it lives up to that name. More than 65 percent of the state’s residents live here, with nearly 10 million visitors arriving each year. This tropical paradise in the middle of the Pacific is a great place to drink mai tais on the beach, but there’s so much more to experience—like traditional and modern arts, a global food scene influenced by locals and immigrants, dramatic landscapes, a rich history and more. Since you’ve come all the way here, why not explore? In this travel guide, we share the best things to do, places to eat, and places to stay while on your trip to Oahu.

Day 1

Forest bathing, vibrant street art and an unforgettable sunset in Honolulu

Two people swimming in a pool. Text on the pool floor reads: “Wish You Were Here!”
The pool at the Surfjack Hotel & Swim Club. Photo courtesy of Elyse Butler.

I wake up a few floors above where the wetlands once were. Until the early 20th century, springs and streams naturally supplied freshwater to Waikiki (which means “spouting freshwater”). Taro patches and fishponds covered the area, feeding the ali‘i (Hawaiian nobility) and the guests they entertained in their coconut groves and gardens.

This coastal neighborhood is still world-famous for its hospitality. It remains the top tourist destination in the state. But, scanning the street scene from my ninth-floor lanai at the Surfjack Hotel & Swim Club, it’s clear that a lot has changed.

I’ve just returned home to Oahu after living abroad and I’m ready to reconnect with this place, beyond the concrete and city skyline.

Sugar-dusted donuts in a pink paper box.
Malasadas from Leonard’s. Photo courtesy of Elyse Butler.

“Need a bath?” asks my longtime friend Elena as she pulls up in front of the hotel to pick me up. She’s not concerned with my personal hygiene—we’re heading to Manoa Valley for a forest bathing experience. But first: fresh malasadas (Portuguese donuts) and chocolate macaroons from Leonard’s, Hawaii’s original malasada bakery.

Driving on Manoa Road, we leave the city and its high-rise buildings behind. Sunlight flickers through the trees on the winding lane to Lyon Arboretum, a 200-acre botanical garden in the foothills of the Ko‘olau Mountains. Just five miles from Waikiki, we’ve arrived in another world.

We meet Phyllis Look, our forest therapy guide and a lifelong Manoa Valley resident, in a gazebo. She explains that the term shinrin-yoku (“taking in the forest atmosphere”) was coined in Japan in the 1980s, although the practice isn’t new. Humans have long found healing in nature, and forest bathing is a way to reestablish our connection to the natural world. “Free medicine, no side effects,” she says.

As we walk through the garden, Look leads us through a series of questions: “How would you cross this bridge if you were 5 years old?” she asks. I pass the walkway and climb the outside railing—I’m feeling younger already. “Listen to the sounds of this place,” she suggests. “What do you notice?” The Oahu ‘amakihi bird (a native honeycreeper) calls. Leaves blow in the wind. “Open your eyes and see what’s in front of you, as if seeing it for the first time.” Taro leaves move left to right, butterflies fly about, and birds soar while clouds sail across the sky. I feel so connected, I half expect to find roots sprouting from my feet.

We share final thoughts under an ‘ulu (breadfruit) tree so heavy with fruit it looks like it’s reaching down to offer some—which turns out to be part of local lore. “According to Hawaiian legend, ‘ulu is a gift from the god Ku,” Look says. “The story goes that when he saw his village suffering a famine, he planted himself. Where Ku was, the ‘ulu tree grew, fed them and kept them alive.” On cue, my stomach rumbles and we say aloha to our guide.

Elena and I drive back toward town, stopping by South Shore Grill for a plate lunch. Typically made of meat or fish, rice and macaroni salad, it’s a meal that provided quick sustenance for workers during the plantation era. I finish the fish plate—grilled ono with macadamia nut pesto, island slaw, and rice—and realize the ocean is so close I can smell the saltwater. Or is that all the surfers dining beside us?

A room with gold-and-red chairs and two thrones and a royal dress on a mannequin.
The throne room at Iolani Palace. Photo courtesy of Elyse Butler.

Elena drops me off in downtown Honolulu at Iolani Palace, a restoration of the royal residence. It was home to Hawaii’s last two monarchs: King David Kalakaua and his sister and successor, Queen Lili’uokalani. The palace was the center of the kingdom’s government and a symbol of innovation (it had electricity years before the White House). In many ways, the building is also a symbol of loss since the Hawaiian language, culture, and traditions were outlawed during that time. It has taken more than a century to revive them, so it’s important to visit. “It symbolizes the heart of the kingdom,” says John De Fries, the president and CEO of the Hawaii Tourism Authority and a Native Hawaiian.

I’m late to meet Jasper Wong, cofounder of the community art center Lana Lane Studios in Kaka‘ako. I’m only a few blocks from Iolani Palace, but it seems I’ve time-traveled a hundred years. The neighborhood has cute restaurants, artisan shops and street art in every direction: murals of Japanese-style cartoon characters, honu (Hawaiian green sea turtles) and more. There are full photo shoots in progress and even a wedding.

Wong helped move this “forgotten district” toward becoming what it is today by creating Pow! Wow!, a nonprofit that invites artists to paint murals on Kaka‘ako’s industrial walls. What began with one mural at the first Pow! Wow! Hawaii event in 2011 has grown to more than 100 murals throughout the islands and multiple events around the globe. “Sometimes the process is more interesting than the final piece,” Wong says.

There’s not enough time to see them all, so I duck into Highway Inn for a snack. This location opened in 2013, but the name is much more respected. Seiichi and Nancy Toguchi opened the original restaurant on Oahu’s west side in 1947, and now their granddaughter Monica is at the helm. I want to eat everything, but I’ve promised to meet Elena at the beach for sunset. So I sample some lomilomi salmon, poi and laulau before returning to Waikiki.

A beach with sunbathers and yellow umbrellas. A mountain and buildings are in the distance.
Waikiki Beach. Photo courtesy of Elyse Butler.

The scent of plumeria and the sound of slack-key guitar reach me before I enter Duke’s—a beachfront spot named after legendary Hawaiian surfer and swimmer Duke Kahanamoku. I go to the Barefoot Bar where I see Elena at a lanai table with views of the surf break and Diamond Head. The glass of Lokelani rosé she hands me pairs perfectly with the sunset in front of us.

At night, we head back to the Surfjack where we’re welcomed by a poolside ukulele player. We grab a picnic table and order pohole (Hawaiian fern) salad and ‘ulu pupus from the hotel restaurant Mahina & Sun’s. When the musician finishes her set, we join the crowd in cheering “Hana hou!” (“Do it again!”) She plays and we order one more drink—a liliko‘i (passion fruit) cocktail called a Here Comes the Sun.

Day 2

A soothing drive, a hot hike and handmade crowns along the coast

A bowl of soup with meat, noodles and mint leaves.
Pho from The Pig & the Lady. Photo courtesy of The Pig & the Lady

No one has ever used “morning person” to describe me, but today I’m too excited to sleep and am up before the sun. With an empty picnic basket and a full day ahead, I meet Elena at the KCC Farmers Market where we get pineapple and papaya, taro chips, macadamia nuts, chocolate and two Koko Crater coffees—all made in Hawaii. We chase the tasty smell of lemongrass and curry to The Pig & the Lady, a Vietnamese street food tent where we order a banh mi and bun xao to go.

Driving toward the eastern side of the island, we pass Koko Head on the left and Hanauma Bay Nature Preserve on the right. “How does anyone keep their eyes on the road?” I wonder aloud as we drive along the dramatic Ka Iwi Coast. The Pacific Ocean’s colors are so varied and vibrant I have to blink to be sure it’s real. Elena laughs. Luckily for us both, she’s the one driving.

We pull off at Halona Blowhole Lookout. After watching sea spray coming up from the lava tube below, we take our towels and picnic basket across the lot and make our way down to a sandy spot nicknamed Eternity Beach. It’s perfect for our picnic but, judging by the way the water is moving, not for a swim today.

Bellies full, we climb back up the rocky trail to the car. We go to the Makapu‘u Lookout to see sea cliffs, Makapu‘u Beach and the islands of Manana and Kaohikaipu—both state-protected bird sanctuaries. And then we go to Waimanalo Bay for a swim before driving to Lanikai. The Ko‘olau Mountains on the way look like green curtains hung from the clouds.

Once in Lanikai, we lace up our boots and follow the handmade signs to the Pillbox Trail. The beginning of the path is steep, but a couple of minutes in we reach a landing with views of Lanikai and the Mokulua islands. The air is still and wet. Sweat beads on my forehead. Fortunately, it takes only about 30 minutes to reach the namesake military pillbox bunkers at the top. I turn in place for the 360-degree view so many times I’m dizzy. Or that could be the heat. I take a big drink from my water bottle just in case.

People swim in the ocean as a geyser shoots out ocean water from the rocks in the background.
Halona Blowhole. Photo courtesy of Elyse Butler.

We didn’t come just to stare at the ocean. We need to get in, so back down the ridge we go. I’m the type to tiptoe into the water. But Lanikai, with its soft sand, cyan sea and graceful palms, seems to whisper, “E komo mai” (welcome). I rush in and lie back, toes peeking above the water. I imagine canceling our plans and staying like this forever. Floating weightless in the water with our faces to the sky, I can hear Israel Kamakawiwo‘ole singing in my head: The sound of the ocean soothes my restless soul. The sound of the ocean rocks me all night long… I’d better get out before I fall asleep.

We head into Kailua, grab a table at Uahi Island Grill and sip liliko‘i margaritas while waiting for the main meal: red curry fish on rice, topped with green papaya salad. “There’s no way I can eat all of this!” I say when I see the size of the dish. “I kind of want more,” I say when the waitstaff returns and finds the plate wiped clean.

As we drive farther up the coast, time seems to slow. Less traffic. More trees. Smaller houses. Fishermen casting lines along the shore. We’re so close to the water, I imagine that if the tide comes up, it could wash over the road.

In La‘ie, we locate the house where Auntie Pat and Kiana’s O’ahu Leis is. The mother-daughter duo offer lessons for making lei po‘o, lei for the head that are often worn for celebrations. Kiana’s young daughter, Kohai, waves for us to follow to the backyard where fresh-cut leaves and flowers are laid out—ti leaves, crotons, song of India, bougainvillea, plumeria and bird of paradise petals. Kiana explains that her mother started making lei po‘o for her and her sister when they were dancing in keiki luaus. Auntie Pat, who is originally from Tahiti, didn’t put her daughters in the typical lei po‘o of that time but in a bigger, bolder, more Tahitian style. “Her style is a rainbow of colors,” Kiana says. “Unpredictable. Big flowers here, small flowers there. A Hawaiian-Tahitian fusion. She’d always have one ready for us for every event. Now, I see it was a labor of love; it takes so much time and is made to show aloha to someone.”

Two hands tying together pink and white flowers to make a lei.
An O’ahu Leis lei po‘o. Photo courtesy of oahuleis.com.

Kiana demonstrates the wili (wrap) technique, using the lauhala leaf and raffia. I’m only a few flowers in when my hands start cramping and my raffia breaks. Auntie Pat adds a new strand and swiftly wraps in several bouquets. We carry on: two leaves, small bouquet, wrap, wrap, repeat. Kiana ties the lei po‘o around our heads and hands us a mirror. Big and bold. We thank Auntie and Kiana, take our lei po‘o and leave on the island’s North Shore. We drop by The Elephant Truck at Sunset Beach for pad thai and Panang curry. We’ve barely driven 40 miles, but we’ve experienced the world.

We check in at Ke Iki Beach Bungalows just as the sun is starting to set and walk down to the sand. The sound of the ocean soothes my restless soul. The sound of the ocean rocks me all night long…

Day 3

Sand dunes, ‘small kine’ waves and aloha ‘aina on the North Shore

A surfer riding a big wave.
A surfer rides a wave at Banzai Pipeline on the North Shore. Photo courtesy of Elyse Butler.

I wake to a text from the surf instructor I’m scheduled to meet later: “Surf came up a bit, so we’re moving your lesson to a protected cove.” I’m not sure I want to find out what “a bit” means. The first time I tried surfing on Oahu was 15 years ago, when a local friend took me out promising the waves were “small kine.” I got pummeled and was too scared to ever try surfing again. I think about canceling for today but decide to take a chance.

A woman in a beach hat walks toward a yellow shack selling food, surrounded by plants.
The Sunrise Shack. Photo courtesy of Elyse Butler.

Elena and I drop by The Sunrise Shack, a health food hut across from Sunset Beach. We meet cofounder Koa Rothman, a professional big-wave surfer who’s happy to chat about his love of the North Shore. “In the winter, it’s the biggest gathering of professional surfers in the world,” he says. “It’s a special place.” I’d love to have his calm energy and fearlessness. He’s surfed waves as big as 60 feet and survived serious wipeouts, and he still goes back out. Koa says he usually has an almond bullet coffee before he surfs and an acai bowl with almond butter and strawberries after. We’ll have the same—hold the big waves, please.

Elena and I drive west until the highway ends at Ka‘ena Point Trail. This lava rock coastline with hidden coves is like a dream. About 2.5 miles down the trail, we reach Ka‘ena Point State Park, one of the last intact dune ecosystems in Hawaii. Two fishermen pass, and we ask if they caught anything. “Dinner,” they reply with a smile. I turn, and the view nearly knocks me over. Both coasts are visible, and we’re standing at the top. Clouds drift over the Wai‘anae mountains and sunlight streams through. I close my eyes as if they’re a camera shutter—I need to hold on to this.

It’s time to head back for my surf lesson. We meet Carol Philips, owner of North Shore Surf Girls at Pua‘ena Point. Safely on the sand, she demonstrates how to paddle, turn and pop up, then asks me to do the same. “You can ride all the way in like this if you want,” she says, modeling a cobralike position. “You don’t have to stand up until you’re ready.”

We put the boards in the water and a sea turtle swims toward me, then loops back out toward the surf as if leading the way. I can see waves rolling in and my heart starts thumping against the board. “I’m right here with you,” Carol says.

We arrive at the lineup and almost immediately she says, “Turn your board toward the beach. Check over your shoulder and get ready.” I thought I’d have more time to watch and wait.

“Paddle!” she yells. “Paddle!” I feel the wave start to lift the back of the board. I push the tops of my toes down and lift my chest up. You can ride all the way in like this if you want. It would be easier. But I don’t want to do what’s easier. I want to surf. I’m picking up speed and hoping the momentum will carry me. I stand up—not perfectly, but I’m up. I find my balance and keep my eyes on the beach. I feel like I’m flying.

I hear cheers behind me. The wave dies out, so I lie down on my board and look back to find Carol riding in on another wave. “How was that?” she calls.

“Was I standing up? And, um, were people … cheering?”

“Yes!”

“For me?”

“Yes!”

A seal lying on the beach shore.
A Hawaiian monk seal. Photo courtesy of Elyse Butler.

We laugh and paddle back out to catch a few more waves before returning to the beach. Just as we reach the shore, a turtle pops its head out of the water, then swims away. I can’t be certain it’s the same one from earlier, but it seems like a goodbye.

Elena and I drive into Hale‘iwa and stop at Surf N Salsa, a food truck serving Mexican-style dishes made with local produce. I eat crispy fish tacos with homemade salsa on top. We also stop by Kula Shave Ice, where I order an organic guava shave ice with a haupia cream top.

Next, we talk with Felicita “Ku‘uipo” Garrido at Na Mea Kupono, a taro patch in Waialua. Na Mea Kupono (meaning “all things proper, or rightful”) is more than a farm. “Our focus is not just kalo cultivation,” Garrido says, “but living the values of aloha and sharing this space so people can connect to the ‘aina (land) and their ancestors.”

In the Hawaiian creation story, Wakea (“sky father”) and Ho‘ohokulani (“the making of stars in heaven”) had a stillborn baby and buried him. Ho‘ohokulani’s tears watered him, and kalo grew. Their second son was named after his brother and fed the kalo. “That’s where the connection began,” Garrido explains. “The older brother sustained his younger brother, and the younger brother must care for his older brother. Aloha goes both ways: You take care of me, and I take care of you. We’re all connected.”

On the way to the lo‘i, we spot some ‘alae ‘ula, an endangered Hawaiian moorhen. “What a blessing!” Garrido says, counting five of them. “You must have good karma.”

I step into the lo‘I to help with clearing invasive species. I’m up to my waist in water, sinking in the mud. Rain begins to fall. Although it’s my first time in the lo’i, there is something familiar: the feeling of being part of my surroundings. Just like when forest bathing, I’m sure I could grow roots.

The rain stops and we go to the punawai (spring) pool to rinse off. We have a dinner reservation at local favorite, Haleiwa Joe’s. But I’m in no rush to be anywhere else. I test the water with my toe. It’s freezing. “You don’t have to go all the way in if you don’t want to,” Garrido says as the rain starts to fall again. I didn’t come here just to dip a toe in, I came to immerse myself. So I do.

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