Breathtaking Views Await Atop Kailua’s Lanikai Pillbox Trail

The Kaiwa Ridge Trail, better known as the Pillbox trail, rewards hikers with a 360-degree view of Lanikai and the Windward Side. 
kailua pillbox oahu kaiwa ridge lanikai hike
Photo: Mike Karas

Moku Nui and Moku Iki. Off in the distance, they sharply rise in a serene sea of aquamarine.

Collectively known as Na Mokulua (“two islands”), they’re Oahu’s most popular offshore islets and protected seabird sanctuaries and it’s the bird’s-eye view of them that entices most people to hike the Kaiwa Ridge Trail—a roughly 1-mile hike better known by its colloquial name, the Lanikai Pillbox Trail.

It’s one of the most popular hikes on the island and can attract hundreds of people on weekends and holidays, all traversing the mountain’s gradual incline to be rewarded with a heavenly glimpse of Na Mokulua. Frequently photographed, painted and even silkscreened, they have become a sort of symbol for Kailua.

pillbox hike
The terrain of the Kaiwa Ridge Trail toward the summit. 

I’ve seen everyone on this trail, from visitors tottering in heels alongside toddlers and terriers to triathletes running up and down in sprints. But, to avoid the crowds, my husband and I head out on a Tuesday afternoon to the quaint suburb of Lanikai, known for its powdery, white-sand beach and high-priced, beachfront homes. The trailhead is tucked in the back of this quiet residential community, just across from the Mid-Pacific Country Club. You have to park in the neighborhood, so be sure to respect the residents living next to the trailhead as you start and finish the hike. The hiking gods smiled down upon my husband and me that afternoon because we immediately found street parking close by.

The trailhead is easy to spot—just follow fellow hikers, or look for the traffic sign reading “The Pillbox” on a paved road to the left of Kaelepulu Drive. The hike starts with an incline for the first several hundred feet; it’s the most challenging part. Our hearts now pumping, we pause along the windblown ridge to take in a view overlooking Kailua. My husband snaps photos of the neighborhood below us. Not even halfway into the hike and we have a sweeping vista of the turquoise sea. “You really can’t take a bad photo on this trail,” he says, firing off a few more.

lanikai pillboxes
Hikers enjoy the views of Na Mokulua.

Our luck continues: We have the trail practically to ourselves, something that has never happened to me during the several times I’ve done this hike. We encounter only four other hikers. To top it off, there is a nice cloud cover—a bonus for this hike because there are no trees providing shade along the way.

The rest of the rocky, dusty trail is a gradual incline. We don’t seem to notice though, when there are neighborhood and ocean views each step of the way. During this hike, not only can you see Na Mokulua and Lanikai, but also the towns of Kailua and Waimanalo, backdropped by the majestic Koolau Mountains and the gorgeous sea.

koolau mountains
A view of the Koolau Mountains along the way.

We get to the first of the two pillboxes in about 20 minutes. But, says military historian John Bennett, technically, they’re not even pillboxes. “They acquired that name somewhere along the line,” he says. A pillbox is a defensive station in which a machine gun would have been installed, he explains. These were observation stations “that were equipped with telescopic instruments.” The two stations were built in early 1943 and cost approximately $8,000 to build ($112,000 when adjusted in today’s dollars).

The trail served as the access point to the two concrete structures. And, while the bunker-like buildings have long since been decommissioned, the views from them continue to be appreciated. There are even other “pillbox” trails, including the easy Diamond Head State Monument trail and the moderately difficult Puu O Hulu, a short but steep trail on Oahu’s west side.

This pillbox hike, the Kaiwa Ridge Trail, can be completed in an hour, depending on how many photos you take atop the two structures. We stop at each one, now brightly colored from graffiti, and weathered from age and heavy traffic. “Michael loves Natalie” and “Keoni was here” are spray painted on the roof of the second pillbox. Standing on top, I pull out my phone to take a photo as my husband flies his new drone out to sea and back. The waves gently roll around Na Mokulua as fluffy clouds float past, creating shadows over the bright blue-green waters.

No matter how many times we’ve hiked the decades-old trail, we always enjoy the destination as much as the journey. That’s what makes this hike so beloved. You don’t need to be in Olympian shape, and you don’t need all day to enjoy this hike. It comprises the perfect hike trifecta: Short and easy, family-friendly and, of course, with awesome views.

Experience more of the Kaiwa Ridge Trail with some gorgeous drone footage. 
Video by Matt Tuohy

Hiking the Lanikai Pillboxes Trail: The trailhead is on the small road to the left of Kaelepulu Drive, just before a gated community and across from Mid-Pacific Country Club. 

Categories: Activities, Adventure, Adventure, First-Time, Hiking, Oʻahu, O‘ahu What To Do, Solo