Arriving in Hawaii from the dead of winter in the midwest (one of their coldest winters on record, no less) in January of 2014 was a sensory overload. I can’t think of another time in my life when I’ve been that completely, overwhelmingly happy. A year and a half later, I still live in Hawaii and it’s still amazing, every single day, but those first few months it felt as though I had been dropped in the center of a massive playground full of all of my favorite things, and I simply couldn’t get enough.
Every day was a new adventure and I was always up with the sun to fill my days with cliff jumping, ocean play, swimming with turtles, hiking hair-raising, razor-thin ridge lines, discovering hidden waterfall pools… It was magic, like those beginning moments of new love. And just like with love, I look back on those days with a sort of wistful nostalgia — not that I love the islands any less now…on the contrary, that love has grown and deepened as I’ve dug deeper into island life, built community, and made it home. But there’s just something about that first new-ness of something that is as exhilarating as it is fleeting.
Lanikai Pillbox Hike is a special one to me because it the first hike I did on the island. When I first moved to Oahu, I lived in Kailua for several months and most mornings I would ride my bike over to Lanikai, hike up the Lanikai Pillbox, and then stop by Lanikai Beach (rated one of the most beautiful beaches in the world) for a swim on my ride home.
With quiet, floral-draped residential streets, powder-fine white sand, and turquoise water, Lanikai is a well-known and beloved Oahu destination. Whether it is for a firsthand glimpse of the award-winning Lanikai Beach or a kayak trip out to the nearby islands, most tourists stop by Lanikai at some point during their stay. It is located just adjacent to Kailua, and is a tiny residential area with a road that loops through it, and no shops or commercial activity. The Lanikai Pillbox trail provides a perfect way to experience Lanikai, offering breathtaking views of the sleepy coastal community as well as sweeping panoramic views of Kailua, Kaneohe, and the coastline in both directions.
This trail is short and non-intimidating, making it popular with families and hikers looking for a fun but not overly challenging excursion. It makes a great pre-beach activity, and can be hiked in approximately 45 minutes, from start to finish.
The trail begins at the end of Kaelepulu Dr. There are a limited number of parking spots there, or hikers can park along the side of Kamahele St (or even better, ditch the car and ride a bike to the trailhead!) After parking, walk up Kaelepulu Dr and turn left to reach the start of the trail. There is a sign marking the starting point, and the first several yards of the trail lead up along a residential property fence line. Once you reach the top of this section, you will step out to be greeted with the first view overlooking Lanikai and the Mokulua Islands. The trail is open from here on out, offering views to both sides of the ridge line.
Also called Ka’iwa Ridge Trail, it is more commonly known as the Lanikai Pillbox Hike because of the two pillboxes (military bunkers) along the way.
There is little shade along the trail and it can get very hot, so bring plenty of water and plan to hike early or late in the day rather than at the day’s hottest point. Please remember to be respectful, as the trail begins in a residential area!
Hike the Lanikai Pillbox Trail
Address: Kaelepulu Dr, Kailua, HI 96734
Directions: From Waikiki, take the H1-W to the Pali Highway. Take the Pali Highway into Kailua. Once you reach Kailua, it will become Kailua Road. Follow it until it ends in a T; turn right onto S Kalaheo Ave. S Kalaheo Ave will become Lihiwai Rd, and then Kawailoa Road. Continue past Kailua Beach Park, and then turn left onto Alala Rd to follow the coastline. Alala Rd becomes Mokulua Dr as you enter Lanikai. It is a loop road to through Lanikai, so once you come down the hill into Lanikai you will directed to keep to the right. Turn right onto Kaelepulu Dr. The trail head begins at the end of this road and to the left.