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Time: 1-2 HOURS

Distance: 0.8 MILES (1st Pillbox), 1.0 MILES (2nd Pillbox), 1.8 MILES (3rd Pillbox)

Elevation Gain: 450 FEET

Foot Traffic: HIGH

Challenges: Dusty, A few steep scrambles with loose dirt, Shadeless, Parking

Sights: Pillboxes, Lanikai Beach, The Mokes, Ko'olau Mountain Range, K-Bay, Maui/Lanai/Molokai

What to Bring: Sunscreen, Water

There's a reason this is one of the most popular hikes on Oahu. You get ridge hiking, you get history, and you get amazing views all in a short and fun trail. Make this hike extra special and do it during sunrise, as you watch the golden light illuminate the windward coast. And after your hike, you can relax at the world famous Lanikai Beach, or grab a meal in the pleasant town of Kailua. Even with the crowds, it's hard to dislike this awesome trail.


Google "best hikes on Oahu" and you can all but guarantee the Lanikai Pillbox Hike (officially Ka'iwa Ridge) will be on that list. While I often prefer the trails less travelled, popular trails are popular for a reason. The Lanikai Pillbox Hike really does have it all. It's short, relatively easy (a couple fun scrambles), and the views are simply spectacular. When I lived in Kailua, I would hike or trail run the pillboxes 1-2 times a month, each time finding the trail just as enjoyable as the last. After moving to "town" (Honolulu), I come here less frequently. But any time I get the invite for a Pillbox sunrise hike, I always accept. That early wake up call is worth it to experience the awesomeness that is the Lanikai Pillboxes.

All you have to do is look at the Google Earth Image to understand why this hike is great. A small little ridge right on the coast, with great views makai (towards the ocean) and mauka (towards the mountain). The islands in the image are the Mokulua Islands or "The Mokes", a pair of islands that serve as a focal point of the hike's views.

The hike begins on Kaelepulu Drive across from the Mid Pacific Country Club. There's a tiny bit of parking along this street, but most people park on Aalapapa Drive. Be warned, parking here is strictly enforced. Make sure your car is parked completely off the road and you aren't blocking any driveways or fire hydrants. Additionally, parking is completely restricted during some weekends for safety reasons, generally holiday weekends. If it is one of those weekends you will have to park all the way back at Kailua Beach Park and walk. If there aren't tons of cars lining the streets, it's probably one of those weekends.

The trailhead is marked, but sometimes the signage is confusing (such as this very misleading sign). You should follow the dirt path that parallels the fenceline shown in the previous picture.

And within no time, the ascent begins. This first section is actually one of the steepest parts of the whole hike. It's a short packed dirt incline to get to those first views. If it has been raining, this section can be pretty muddy and slippery.

But after you make it up that first incline, you will get rewarded with those lovely views. I love the way the sun is bursting over the horizon and illuminating the Mokes and the rest of Lanikai. Can you tell why this is one of my favorite sunrise spots?

But we still have a destination-- the Pillboxes! Follow the natural path of the ridge as you continue the ascent.

The path isn't hard to follow, although you will come across a couple rock walls like this. While there is a bit of minor scrambling required to get to the pillboxes (you will actually have to use your hands), if you're doing anything that feels extreme, there's probably an easier path nearby.

So really, the hike is a game of finding the path that is comfortable for you.

As you progress, don't forget to take a look mauka at the beautiful Ko'olau Mountain Range. I love that redish glow reflecting the morning sunlight. Those prominent peaks on the left are part of Mount Olomana (AKA Three Peaks), an epic advanced ridge hike.

Aloha Pillbox Number 1! Fun fact, the term pillbox apparently is an incorrect way to describe these structures. Pillbox implies there is some sort of defensive armament. These were observation posts constructed to spot enemy ships (info courtesy of How you choose to enjoy these structures is up to you. You can climb on top and take a seat. You can explore the inside. You can snap a few pics and move on to number two.

Or you can find your own personalized spot away from all the noise of the pillbox and soak in that morning light.

Onward! It only takes a few minutes hike between pillboxes 1 and 2.

The second pillbox is bigger, with 2 levels of platforms to sit or stand on, so there's a bit more space for chilling (or selfies).

Ka'iwa ridge continues past the 2nd pillbox and does actually have a "third pillbox." This pillbox is underwhelming, it's basically a cement block, but the hike to get there is quite beautiful. This photo was from a different adventure on Ka'iwa ridge and is still one of my favorites.

Another way to see the full expanse of this ridge is from the air!

But actually though.

The best hike on Oahu? I'm not sure. I think that assessment is an individual preference. Nevertheless, I'd say the Ka'iwa Ridge makes a pretty good case.

Have you experienced this amazing place? Share your story below!

Also Check Out:

- Lanikai Pillbox official website for more information on the hike

- My Gopro and Drone video of this hike

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