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

Drive through 13 ahupua‘a as you shop for vintage and new finds, explore a hidden garden and eat your way up the eastern coast of O‘ahu.


Kahana Bay

Kahana Bay. Photo: Aaron K. Yoshino


Driving the Windward Side gives you a chance to appreciate the chiseled sweep of the Ko‘olau Range, which runs from Makapu‘u to Kahuku, as well as the 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 malassadas 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. Avoid the crowds (and Instagrammers) streaming up Ka‘iwa Ridge and head for the much more serene Kaiona Beach Park in Waimānalo.


Oahu Hawaii Road Trip Agnes Malassadas

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


If you haven’t devoured all the malassadas 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 the new sign for Hūnānāniho, the original name of Waimānalo Bay Beach Park (or Sherwoods), which was restored in 2021.


Kaiona Beack Park Waimanalo

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



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. 



Hawaii Road Trip Bookends Kailua

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


Park in the free lot behind Longs Drugs Kailua, 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. 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 and Goodwill Industries (that was once a VW dealership) branches.


Oahu Hawaii Road Trip Protea Waste Kailua

Protea Zero Waste Store. Photos: Katie Kenny


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. Go to Wilson Store to grab a shave ice snack. Ask for bits of lemon peel as a topping, 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.)


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


Hawaii Road Trip Kailua Coco Trading Post 2

Hawaii Road Trip Kailua Coco Trading Post 1

Coco’s Trading Post. Videos: Katie Kenny




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. 



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


Friendship Garden Kbayview Robbie Dingeman Copy

Friendship Garden Bamboo Robbie Dingeman Copy

Friendship Garden. Photos: Robbie Dineman


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.



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.” 



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.


SEE ALSO: Now You Can Eat Shrimp Raised On-Site at Kualoa Ranch


Hawaii Road Trip Kualoa Ranch Oysters

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



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.



Kbay Bros Poke

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


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: The Essential Guide to Taro: Where to Buy Poi in Hawai‘i


Hawaii Road Trip Wilson General Store Kailua Shave Ice

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



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



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

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.