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Lanikai Pillbox Hike (Ka’iwa Ridge) on Oahu, Hawaii – Compete Guide

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The Lanikai Pillbox Hike, also called the Ka’iwa Ridge Trail, is one of the most jaw-dropping trails in Oahu, providing stunning views over Lanikai Beach, the turquoise Pacific Ocean, and the lush Koʻolau Mountains. But what makes this hike even cooler is that you’ll also get to hike to two historic army bunkers from World War II, perched on top of the rolling hilltops of Oahu. Here’s everything you need to know about the Lanikai Pillbox Hike.

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Woman sitting on a pillbox along the Lanikai Pillbox hike, overlooking Lanikai Beach on Oahu
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The Lanikai Pillbox hike is easily one of the best hikes on the island (which, on an island that’s FULL of epically cool trails, is saying a lot!) and is a must on any Oahu itinerary. Not only does it boast breathtaking views of both the coastline and mountains, it’s also relatively short and manageable for hikers of almost every skill level. Sound like a dream come true? Let’s get into it!

Woman standing on top of a pillbox along the Lanikai Pillbox hike in Oahu

About the Lanikai Pillbox Hike

  • Length: 1.7 miles
  • Elevation gain: 626 feet
  • Difficulty: Moderate. The climb up to the first pillbox is pretty steep, but it’s also quite short—less than a mile!
  • Dogs: Furbabies are welcome, but they must be on a leash.

How to Get to the Lanikai Pillbox Hike

The main Lanikai Pillbox trailhead is located here, just a few blocks from Lanikai Beach in the sleepy town of Kailua on the eastern side of Oahu.  

The trailhead is located in a residential area, so there’s no designated parking lot for this hike. In fact, when my husband, Justin, and I visited, there were temporary signs along all of the streets within a mile or so radius of the trailhead, prohibiting street parking. We wound up vulturing for a spot at the Kailua Beach Boat Ramp lot, about 0.6 miles from the trailhead.

View of Kailua from the Lanikai Pillbox hike in Oahu

Per my understanding, this blanket prohibition on street parking isn’t typical and you can usually find a few spots along Kaelepulu Drive, near the trailhead. Just be sure to steer clear of “No parking” signs, red curbs, and residential driveways—Kailua police are not shy about giving tickets around these parts!

It’s also worth mentioning there is a second, less popular trailhead, located here, that’s often referred to as “the back way” to the Lanikai Pillboxes. This, too, is located in a residential area with limited parking and its trail has approximately the same elevation gain, distance, and difficulty. Ultimately, I don’t think your experience is going to significantly differ one way or the other, but since I hiked from the “front” trailhead and it’s by far the most popular route, I’m mainly going to describe that way.

What to Expect on the Lanikai Pillbox Hike 

The Lanikai Pillbox trailhead is pretty obvious, as there’s a big ol’ sign to the right of a residential driveway. Right away, you’ll start climbing up a dusty hill, with lots of roots and rocks jutting out of the dirt. 

Be prepared—the first 0.3 miles or so of this hike is STEEP, so much so, that there’s ropes in a few sections to help you climb up. While this hike isn’t technical, there are definitely areas with steep drop-offs where you could seriously hurt yourself if you happened to fall—accordingly, I don’t think this would be a great hike for little kids.

Woman walking along the Lanikai Pillbox hike with mountains in the background

Eventually, the trail will even out for a bit and you’ll finally get some of your first views of the sparkling turquoise water to your left and to your right, the rolling green mountains.  The further up you climb, the better the views get!

There’s one last challenging push before you reach the first pillbox—it’s so steep, in fact, you might have to scramble up it in certain sections.  This section is quite short, though and soon, you’ll reach the first pillbox. It’s probably the most photographed pillbox on Oahu, with its colorful graffiti and expansive views of Lanikai and Kailua Beach below. 

Couple sitting on the Lanikai Pillbox along the Lanikai Pillbox hike in Oahu

The pillboxes on the hike were originally built in 1943 to serve as observation towers in World War II to look out for incoming Japanese planes or ships, due to their high vantage point. While you (hopefully) won’t see any incoming enemy warfare from here these days, I can confirm the pillbox still serves as an excellent viewpoint over the eastern coastline of Oahu!

Continuing along the rolling ridgeline, you’ll hit a second pillbox just 0.1 miles ahead. The second pillbox is actually a bit bigger than the first one and usually considerably less crowded.  It’s not quite as Instagrammable as the first one, but you still can’t beat those views!

Woman standing on top of a hill overlooking Lanikai Beach along the Lanikai Pillbox hike

Most folks turn around once they reach the second pillbox, but the trail technically continues on for about another quarter mile, as the Koʻolau Mountains loom ahead. Once you’ve had your fill of the Ka’iwa Ridge, simply retrace your steps back to the trailhead!

When should I hike Lanikai Pillbox Hike?

Lanikai is one of the most popular sunrise Oahu hikes and I can totally see why. While I didn’t do this as a sunrise hike, I have seen sunrise at Lanikai Beach (which this hike directly overlooks) and I can confirm that it’s probably the most spectacular place I’ve ever witnessed the sun eclipse the horizon. 

Couple holding hands watching sunrise at Lanikai Beach on Oahu

Besides, y’know, enjoying pure and unencumbered natural beauty at sunrise, your early morning wakeup call will also provide you the amazing benefit of having a better chance of snagging a good parking spot, enjoying a less crowded trail, and avoiding hiking when the sun is at its most brutal (there’s practically no shade on the trail!). Just don’t forget your headlamp and give yourself plenty of time to make it up the steep hill before the sun comes up!

While less popular, it would also be magical to watch the sun sink below the impossibly green Koʻolau Mountains in the evening. 

Sunrise over Lanikai Beach from the Lanikai Pillbox Hike

In terms of what time of year to visit, great news—Hawaii is pretty much perfect to travel to year round! However, winter in Hawaii tends to be a teeny bit more on the rainy side and, given how steep and slippery this trail is when it’s dry, I’d recommend avoiding this hike when it’s raining or if the trail’s wet.

Tips for the Lanikai Pillbox Hike

  • It’s HOT. As mentioned above, there’s basically no shade as you climb up a very steep and dusty trail. Be sure to bring plenty of water (Justin and I both have these comically enormous Nalgene bottles and LOVE them) and sun protection, like sunscreen and a hat. 
Woman walking along the Lanikai Pillbox hike with Kailua Beach in the background in Oahu
  • Wear shoes with traction. Listen, you’re going to be climbing up a steep, dusty, and occasionally very slippery hill. So come prepared with shoes that were actually made for hiking with traction on them, like hiking boots (Justin has this pair and I have this pair) or hiking sandals (we both have a cult-like love for our Teva sandals—check out his and hers).
Man standing on the top of a pillbox along the Lanikai Pillbox hike in Oahu
  • Be respectful. Technically, both trailheads to access the Lanikai Pillbox hike cross private properties via easements—which can be taken away by the private land owners if people act like jerks by parking where they’re not supposed to, leaving trash on the trail or along the roadside, and just generally being, well, jerks!

    Treat the trail (and while you’re at it, the rest of Hawaii!) with the care and respect it deserves and leave it better than you found it. 
  • Explore the east side of the island. Completing the hike should really only take you a couple of hours, but be sure to carve out some time to explore around the eastern side of the island, which is full of sleepy beach towns and Jurassic Park-y vibes. 

    For example, both Kailua and Lanikai, just a short walk from the trailhead, are two of the best beaches in Oahu—in fact, the Travel Channel has voted Lanikai as one of the most beautiful beaches in the world! 

    Alternatively, if you still want to do more hiking, there’s plenty of other cool trails in the area, such as the Koko Crater trail, which provides incredible views over Honolulu and Hanauma Bay, or Makapu’u Point Lighthouse Trail, one of my favorite easy hikes in Oahu that follows a gently sloping path up to a historic lighthouse.
Sunset at Koko Crater trail overlooking Honolulu, Oahu

Where to Stay Near the Lanikai Pillbox Hike

By car, the Lanikai Pillbox Hike is about a half hour drive from Honolulu, where most travelers elect to stay in Oahu, or, if you’re taking public transit, it’ll take a little over one hour.

The Equus: The Equus is one of our favorite budget hotels in Honolulu. With charming decor, exceptional hospitality, and a close proximity to shopping and dining near Ala Moana, few accommodations match the value offered here.

Outrigger Waikiki Beachcomber Hotel: This resort offers a more upscale experience with a modern decor, stunning views from each room, and on-site access to Maui Brewing Company, Hawaii’s largest craft brewery and the beautiful Aroma Hawaiian Caffe, serving up come of the most delicious drinks made from beans grown right here in Hawaii.

I hope you have the best time exploring the Lanikai Pillbox hike—it’s one of the most incredible trails on Oahu! Do you have any questions about the trail? Let me know in the comments below!

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