Lanikai Pillbox Hike – Oahu, Hawaii

The Lanikai Pillbox hike (a.k.a. Kaiwa Ridge) is a favorite on Oahu for visitors and locals alike. It’s a quick climb for scenic views of beautiful Lanikai beach, the Ko’olau mountains, and Kailua town.

This is a moderate hike due to the terrain. It’s not very long, but it does get pretty steep in the beginning. Also, the path is rocky with some loose dirt, which can quickly turn slippery if there’s any rain.

Panoramic views abound as you climb. It is only 0.4 miles from the road to reach the first pillbox, overlooking the Lanikai beach, neighborhood, and the Mokulua islands. This is a great spot to catch the sunrise (and escape mid-day heat for your hike).

There are some sections of this hike with multiple ways to go up. Don’t worry too much about which way you go, as long as you’re comfortable, safe, and heading in the direction of the pillboxes.

The second pillbox is just another tenth of a mile from the first. These, are of course, where the hike gets its name. They were once used as military bunkers to look out over the ocean.

As you can see, the pillboxes have been colorfully graffitied and provide a great resting point to enjoy the views.

Most visitors turn around and head back at the second pillbox. The trail does continue along the ridge, if a little overgrown at times. Once you can see the sandy Bellows Air Force Base beach down below, you’ll enter a treed section of the path and then come upon a fork in the path. Take a right at the fork to go downhill toward the Enchanted Lake neighborhood – or turn around for an out-and-back hike.

It’s about 1.3 miles from the trail head to end up on Kamahele Street. The road back to the start goes through a gated community of Bluestone, but there is a pedestrian entrance gate – we didn’t try it, as we were getting picked up from the nearby Enchanted Lake shopping center.

Directions to the Pillbox Hike

This hike is located in the Lanikai neighborhood of Kailua town, about a 30 minute drive from Honolulu.

The trail starts on a small side street off of Ka’elepupu Drive, near the entrance of the Mid-Pacific golf course. There are a few parking spots along the road not far from the entrance. Pay attention to parking signs in the neighborhood, as they get tons of visitors and sometimes tow when necessary.

Note that Lanikai Beach gets very crowded on weekends and in high season; and because there’s only one entrance/exit to the entire neighborhood, traffic can back up like crazy.

Pillbox trailhead heading up along the road

What to bring:

• Sunscreen – there is very little shade
• Water
• Sturdy shoes with grip
• If you have a hiking stick, it wouldn’t hurt for going back down the loose rocks!

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