Oʻahu Hike of the Month: Lanikai Pillbox Trail

A quick trek with a breathtaking view in Kailua.

By Lennie Omalza

Photos: Lennie Omalza

TRAIL NAME: Lanikai Pillbox Trail

DIFFICULTY: Moderate

LENGTH: 1 mile roundtrip

FEE: None

WHERE: Kaelepulu Drive, Kailua

DISCLAIMER

Hiking can be dangerous, and not every trail is a good idea for every person. Keep your personal fitness and skill levels in mind, and always take proper precautions when venturing off road. Heed “no trespassing” and other warning signs.

THE EXPERIENCE

​Kaʻiwa Ridge Trail, more commonly known as the Lanikai Pillbox Hike, is a dirt trail that includes some rocky and gravelly sections. Located in a residential area on Kaelepulu Drive, the start of the hike is clearly marked with signs that lead to the entrance, a narrow path between two fences. From there, the uncovered trail ramps up quickly. Fortunately, you can use a rope tied to a line of trees for support during one particularly tricky part of the uphill trek. Before reaching the first pillbox, there are two flat areas where you can rest if needed. From there, the second pillbox—with an amazing view—isn’t much farther.

Heading back down is trickier than going up. The gravelly areas can be slippery, and the trail doesn’t seem as clear as it was going up; we went down the wrong way in one area and had to head back up to find the correct path. Upon further investigation, we discovered black arrows on the ground, pointing hikers in the right direction.

(Fun fact: The “pillboxes” were military observation stations during WWII. Because they weren’t used for defensive armament, “pillbox” is technically an incorrect term for the concrete bunkers.)

Photo: Enjy El-Kadi

THE PAYOFF

The view from the second pillbox is impressive, overwhelming, stunning, beautiful. We spent more time sitting up on the old bunker taking in the view than we did hiking. There is nowhere else on the island that offers such a magnificent perspective of Windward Oʻahu, the Mokulua Islands or the clear blue waters that give Lanikai its name.

MAP & DIRECTIONS

Head past Kailua Beach Park, into Lanikai. Kaelepulu Drive will be on the right. The start of the hike is on the left of the street, across from the Mid Pacific Country Club.

TIPS

Apply lots of sunscreen before getting started; this is a completely uncovered trail and, unless it’s an overcast day, it will be very hot.

Don’t attempt this hike after it’s been raining. With some parts of the trail already a bit slippery, imagine what the ground is like when it’s wet.

Though we didn’t see any children or dogs during our visit, other hikers have been known to bring along their two or four-legged keiki. Do so at your own risk. As previously mentioned, the trail can be both slippery and hot. In fact, in 2015, KHON2 released a warning about dogs getting heatstroke on this hike.

Consider parking at Kailua Beach Park and walking to the start of the trail. Because it is a residential area, parking is extremely limited and many cars have been towed.

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