The Lanikai Pillbox hike has exploded in popularity over the last decade to become one of the most popular hikes on O'ahu. It is no surprise when you see the photos. Additionally, the hike is short, accessible and surrounded by a ton of other fun activities. Here you compete with tourists and locals alike as you try to find a quiet moment to yourself. Approaching this hike in the standard way can mean some big crowds.
Luckily there is another way to experience the stunning scenery of Lanikai Beach and eastern O'ahu while reducing the crowd by 90%. You'll also get views of Waimanalo and the Ko'olau Mountains that are hard to find otherwise. This route might be accurately calld "backwards and the long way." It starts at the far southeastern end of Lanikai and works against the grain back toward the pillboxes. The trail is much longer this way, and it is also much more rewarding and peaceful. The start of the trail from Luika Place is not much more than a dirt path between two houses covered in tall grasses that gets real vertical real quick. You gain almost 300 feet in the first 500 yards; there are some trees and roots to help pull yourself up, but the trail is unstable in places, so do not attempt it if there have been heavy rains.
Once atop the first short and grueling stretch you are immediately rewarded with a close up view of the iconic Mokulua Islands just off the coast of Lanikai Beach. The vista is stunning as you try and catch your breath from the ascent. To your right is the picturesque and often overlooked Waimanalo Bay. Rabbit Island, or Manana Island, sits off in the distance as you look toward the popular Sea Life Park.
The trail heads south, west, and eventually north as it rounds back toward the traditional start of the Pillbox Trail. There is a fair bit of elevation gain and descent, and there are many exposed areas, so water and sunscreen is a must. The views of Olomana's three peaks with the Ko'olau Mountains behind is quite a sight to behold.
When you do the final ascent up to the pillboxes, constructed during World War II, the crowds quickly fill in. There are two bunkers, one up high and another one lower on the trail. The views from here are amazing as well, but they are harder to enjoy with the limited elbow room. As you make the final descent after leaving the bunkers you will have to navigate the many people coming up trail, and you will quickly appreciate having most of the trail to yourself in the early going. Finish off the hike by walking toward the ocean on Kaelepulu Road and take a right onto A'ala'papa Road just as you drove in.