The Lanikai Pillbox Trail along the Ka’iwa ridge is one of my favorite hikes in Oahu. The trail is relatively easy and the reward is great! The distance to the second pillbox is 0.6 miles each way. You can complete the trail in about 1 hour or less; though, you will want to spend some extra time at the top enjoying the unobstructed 360-degree views of the surrounding area, such as the beautiful Koolau Mountain Range, Kailua Beach Park, Lanikai Beach, Mid Pacific Country Club, Mokulua Islands and Waimanalo Bay.

During the hike, you will face a gradual inclination of about 612 ft with few obstacles on the way. The trail begins with a very steep and slippery incline due to the loose dirt. Grab onto ropes and trees to keep from sliding back down. This part is especially difficult on the way back, so be sure to hang on to something, or you may find yourself rolling down the hill! Once you make it past the initial slope, the rest of the way is relatively easy to navigate. The path, however, is very narrow in parts along the ridge, and there are areas where there is room for only one person to pass. As long as you stay away from the cliff, you should be okay. Use caution and hold on to a stable rock or a bush while allowing others pass.

Most of the trail is unshaded; therefore, I recommend going at dawn or dusk to avoid the sun. If you must do the hike during the day, be sure to bring plenty of water and sunscreen! The trail can be dangerous for kids as there are no guard rails; that said, with a little help, my 5-year-old daughter enjoyed the hike. We also saw plenty of other families with children along the way.

The two “pillbox” structures that you will encounter are remnants of WWII. They are incorrectly referred to as “pillboxes” because, in military terms, a pillbox is an artillery defensive site. The the pillbox structures on the trail functioned as Coast Artillery observation stations in 1943 and were not equipped with weapons, but rather high-powered observing instruments used to calculate the position of a ship from the station.

Street parking is limited, be sure to follow street parking rules as parking in a bike lane will result in a $200 summons. We parked our car at Kailua Beach Park and walked to the trail head.

Take a look at the photos below to get an idea of what you should expect to see.