A Local’s Guide to an O‘ahu Road Trip: Waimānalo to Kahana

Editor’s Note: This story, first published in April 2022, has been updated with the latest info and more fun. 

Kahana Bay. Photo: Aaron K. Yoshino

Walk Waimānalo Beach

Summer seems like the best time to drive through Windward O‘ahu because it reminds us of childhood fun. A leisurely journey lets us appreciate the chiseled sweep of the Ko‘olau Range as we trek from Waimānalo to Kahana. And we’ll dip into those turquoise waters lapping at long sandy stretches of coastline.

Start early to enjoy the natural beauty—created by a volcano that first erupted an estimated 2.5 million years ago—at a slower pace. Get a sweet start with malasadas from Agnes’ Portuguese Bake Shop (a food truck reboot of the popular Kailua bakery that shuttered in 2018) in the parking lot of Kailua-born brand Manuheali‘i. Sometimes, you’ll find veteran baker Non DeMello serving up the fried treat. Then avoid the crowds (and Instagrammers) streaming up Ka‘iwa Ridge and head for the much more serene Kaiona Beach Park in Waimānalo.

Malasadas from the Agnes’ Portuguese Bake Shop food truck. Video: Katie Kenny

If you haven’t devoured all the malasadas in the car, snag a picnic table with a view of Mānana (aka Rabbit Island). Then walk left past fishers, snorkelers and outrigger canoes awaiting the next practice. After that leisurely stroll, return to Kailua along Kalaniana‘ole Highway, past horses grazing roadside, and check out the sign for Hūnānāniho, the original name of Waimānalo Bay Beach Park (or Sherwoods), which was restored in 2021.

Views of Kaiona Beach Park in Waimānalo. Photos: Robbie Dingeman

♥
DID YOU KNOW
In the 1920s, Theodore and Mary Atherton Richards sold land in town in Kauluwela to use as a down payment to buy the 39 acres of Kokokahi that includes the Friendship Garden in Kāne‘ohe. The price was $45,000.  

BookEnds is a well-loved independent bookstore stacked high with local books, bargains and bestsellers. Video: Katie Kenny

Breakfast Choices Abound

Back in Kailua, if you skipped the malasadas and the shops aren’t open yet, you’ve stopped in the neighborhood of best breakfasts. Our family thinks of kama‘āina restaurant Cinnamon’s as pretty much synonymous with pancakes: guava chiffon, red velvet, banana and more. And someone at our table always order eggs Benedict with made-to-order Hollandaise too.

Looking for a modern take on breakfast? Over Easy offers some of our favorite reasons to leave the house. Potato ‘n’ Eggs is a twist on eggs Benedict with a creamy potato purée spooned over the eggs. And the brunch bowl brings together soft-cooked eggs, avocado, house-made tomato jam and yogurt, zesty greens, candied bacon and a couple slices of sourdough.

Want to get back on the road faster? Within Over Easy, Bake Side sells a mix of tasty pastries and some savory choices too. Another popular hearty dish is kalua pig hash, which heaps kalua pork atop Okinawan sweet potatoes and fingerling potatoes and lomi tomato.

SEE ALSO: Kailua Brunch Spot Over Easy Expands With a New Grab-and-Go Shop

Brunch bowl and Potato ‘n’ eggs at Over Easy in Kailua. Photo: Robbie Dingeman

Craving the comfort of an old-school diner? Head to Times Coffee Shop on Hāmākua Drive and make sure someone orders the fried rice. We love the vegetarian version, but this is also the place to indulge yourself with a loco moco since the hamburger patties are made in-house.

Coco’s Trading Post. Videos: Katie Kenny

Shop Books, Art, Local Finds

When you’re ready to shop, park in the free lot behind Longs Drugs, then walk to BookEnds, a well-loved independent bookstore stacked high with local books, bargains and bestsellers. Next, some retail therapy. Coco’s Trading Post stocks a mix of made-in-Hawai‘i décor, accessories and clothes for all ages.

Cross the street to see the latest vintage-inspired surf-and-travel-focused art from Nick Kuchar. We’ve always appreciated his nostalgic style, but we’re really looking for a reason to buy his new motel-style Meet Me in Kailua keychain.

Since the OG Pali Lanes closed, there’s no bowling, but you can pick up another favorite sport of sorts: thrifting! We consistently spot great finds in the sprawling Salvation Army store here. We need to travel a little further to reach the Goodwill Hawai‘i store since the Windward shop moved from Kailua to Kāne‘ohe in 2022.

Protea Zero Waste Store. Photos: Katie Kenny

Get Eco-Friendly Products and Snacks

Stroll a few minutes to Protea Zero Waste Store for chic and sustainable nontoxic products. Got a clean empty container? Fill it with lavender laundry detergent or lemony disinfectant.

Then head to Wilson Store to grab a shave ice snack. Ask for bits of lemon peel as a topping and eat outside before you jump back in the car and drive 20 minutes to Kāne‘ohe. Masa & Joyce Okazuya offers a light hand-held lunch: wasabi ‘ahi hand roll, Spam musubi and maki sushi. (Can’t resist the nishime, mac salad or garlic chicken? Stick it in your cooler for later.)

Go to Wilson Store to grab a shave ice snack. Video: Katie Kenny

SEE ALSO: Shades of Shave Ice: Kailua’s Neighborhood Shops With Shave Ice Counters

♥
DID YOU KNOW
Waimānalo is the largest ahupua‘a in the moku (district) of Ko‘olaupoko, extending from the ridge behind Keolu Hills, around Makapu‘u and ending at Kuli‘ou‘ou Ridge. In creating modern ahupua‘a markers, the Hawaiian Civic Clubs and Neighborhood Boards used a map from 1876 done for the Kingdom of Hawai‘i and recognized by the ali‘i before the overthrow of 1893. 

View of the bay from the Friendship Garden. Photo: Robbie Dingeman

Friendship Garden. Photo: Robbie Dingeman

Hike a Hidden Gem

Drive 3 miles to the Friendship Garden, a privately owned historic hidden gem that welcomes the public during daylight hours. The 10-acre park was developed in 1927 as part of a multiethnic neighborhood dedicated to harmonious living called Kokokahi, which translates to “one blood.” Parking is limited, so carpool or have a friend drop you off. The hourlong loop trail  trail includes a stunning view of the bay, a bamboo grove and a shady stone amphitheater where you can pause to picnic.

♥
DID YOU KNOW
Historian Samuel Kamakau noted that Kualoa in ancient times was “a very sacred place of refuge in where a man condemned to die was saved if he entered.” 

K.Bay Bros poke bowl. Photo: Aaron K. Yoshino

Buy Local Poke and More

A 15-minute drive leads to K.Bay Bros. Fish & Ice. Grab a protein-heavy snack—kim chee shrimp, tako dynamite, boiled peanuts—toss it in the cooler and head up the coast. See fruit stands, flower farms and “Keep Country Country” signs on the way to Kahana Bay, which is part of Ahupua‘a ‘O Kahana State Park.

Wear a swimsuit to splash around in the family-friendly waters off this stunning crescent-shaped beach. Just down the road, shop at the Kualoa Ranch market and marvel over the homegrown bounty: frozen shrimp (fresh shrimp sells out quick), oysters, sausages, teri beef already marinating, kalo to kohlrabi and even bouquets of ginger and heliconia.

Shuck a dozen fresh Kualoa Ranch oysters at the beach and enjoy the rest of your road trip treats. Video: Katie Kenny

SEE ALSO: Mālama ‘Āina: Caring for the Land

♥
DID YOU KNOW
The brown-and-white ahupua‘a boundary markers along the Windward Coast were initiated in 2009 by the Ko‘olaupoko Hawaiian Civic Club.  The pig’s head above the stones replicates a symbol used in ancient times.

Take Home Hawaiian Food

Don’t get stuck in line at Waiāhole Poi Factory. Call in or order your dinner online: hand-pounded poi, of course, but also meaty pork-filled lau lau, squid or beef lū‘au and haupia for dessert. Pick it up to share with those who couldn’t holoholo with you or stop for a picnic on the way home.

SEE ALSO: A Local’s Guide to an O‘ahu Road Trip: Wahiawā to Salt Lake 

Waimānalo to Kahana Itinerary

7:30 a.m: Pick up malassadas from Agnes’ Portuguese Bake Shop food truck, then drive to Kaiona Beach Park in Waimānalo.

7:45 a.m: Take a just-past-sunrise walk. Head back along Kalaniana‘ole Highway to Kailua.

9 to 11 a.m: Shop for books, vintage and new finds and shave ice with a tart surprise.

11:15 a.m.: Pick up a portable takeout lunch—hand rolls or bento—at Masa & Joyce Okazuya.

Noon: Hike at the historic Friendship Garden above Kāne‘ohe.

1:30 p.m.: Drive 15 minutes to K.Bay Bros. for poke and ice for the cooler.

2 p.m.: Swim, eat and enjoy the crescent-shaped beach at Kahana Bay.

3:30 p.m.: Buy what’s in season: local produce, protein and flowers at the Kualoa Ranch market.

4 p.m.: Call Waiāhole Poi Factory or go online to order Hawaiian food for dinner.

SEE ALSO: A Local’s Guide to an O‘ahu Road Trip: Waialua to Kahuku