There was a time when I spent a lot of time in Kailua.
I’d meet up with friends on Kailua Beach in the late afternoon, all of us leaning back in beach chairs, strumming guitars and dishing about the guys we (OK, they) were dating. We’d get up before sunrise to hike to the pillboxes at the top of Kaiwa Ridge overlooking Lanikai and gaze at the Mokulua Islands offshore and the iwa (great frigate birds) seemingly suspended in the sky. Later, my husband and I would hit the surf at the north end of Kailua Bay, at a break called Castles, when the trade winds were light and the afternoon sun was just dropping over the Koolau Mountains. We’d kayak to Moku Nui, the larger of the twin islets, and snorkel, fish and catch waves. Or we’d stroll along the golden stretch of Kailua Beach on the weekend, dogs in tow, breathing in the salty air and believing the saying, #luckywelivehawaii.
It was a time when you could actually find a quiet spot on Lanikai Beach and street parking along Hekili Street, when Boots & Kimo’s was a hole-in-the-wall eatery with just six booths and a few tables with stools.
Kailua has definitely changed over the last two decades. Some of my all-time favorites—Agnes’ Portuguese Bake Shop, Andy’s Drive-In, Mama’Nita Scones—are gone, but so many great restaurants, coffee shops, boutiques and family-run shops are still around—and more have popped up in recent years. The HAWAII team spent a few days in Kailua, sampling shave ice, chatting with business owners and walking the 2.5-mile Kailua Beach—yes, on company time!—to find hidden gems, overlooked spots and interesting stories in this beachy neighborhood. And, to be honest, Kailua exceeded our expectations—even my own memories. What we found was a community that has gracefully figured out a way to invite strangers, including this group of curious writers from Honolulu, while retaining what has long made this place so special.
The last time Kailua was featured as our cover story was back in 2010. The late John Heckathorn, then the magazine’s editor, wrote this about the town: “Kailua is a genuine small town, friendly, relaxed and beachy. It may also be one of the most beautiful towns in Hawaii.”
We can confirm: It still may be.
MY 3 KAILUA PICKS
1. The potato ’n’ eggs at the brunch spot Over Easy (418 Kuulei Road, overeasyhi.com) combines thick-cut French bread with sweet tomato jam and a silky potato purée that’s deliciously unique.
2. The 3-mile Maunawili Falls Trail (off Auloa Road) meanders through massive monkeypod trees and ends at a scenic waterfall in a cool, swimmable pool. Respect the neighborhood, use bug spray, wear sturdy shoes and watch the weather.
3. If you have keiki in tow, Pohakupu Mini Park (1329 Kailua Road) is a quiet and safe playground surrounded by trees. And the swings have bucket seats!