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Need to know




For such a short hike (about 30 minutes or so to the first pillbox), the Lanikai Pillbox Trail has one of the most beautiful views. You may have seen cool pics of people dangling their legs off the edge of a graffitied pillbox, with the turquoise ocean in the background. In the distance you can see the Mokulua Islands (The Mokes) and just below is the white sand of Lanikai Beach and a scattering of palm trees along the coastline. 

There are 2 pillboxes on this trail that both face the ocean. Get to them before the sun comes up and you’ll be rewarded with one of the most breathtaking sunrises on the island. The sun comes up behind the Mokulua islands, lighting up the ocean, sand, and neighborhoods down below.


It’s a short hike, but it’s along a dirt trail and the first bit is pretty steep, with loose gravel, so swap your flip flops for sneakers. 


Kailua and Lanikai Beaches are two of the most beautiful beaches in the world. Definitely the perfect spots to cool off after this hike.



265 Kaelepulu Dr

Kailua, HI 96734




Easy / Moderate

The trail is short (about 2 miles roundtrip) but it’s steep at the beginning.

Time Estimate

About 1.5 hours out and back - but allow more time for hanging out, enjoying the view at the top.


  • Kailua Beach — 6 min drive (or 17 min walk)

  • Lanikai Beach — 7 min walk

  • GOEN Dining + Bar — 8 min drive

  • Nalu Health Bar & Cafe — 10 min drive

  • Cinnamon’s — 10 min drive

  • Boots & Kimo’s Homestyle Kitchen — 11 min drive

  • Moke’s Bread & Breakfast — 11 min drive

  • Kualoa Ranch — 40 min drive

Short hike with an insane view of turquoise water and the Mokulua Islands. One of the prettiest places to watch the sunrise on the island.

Lanikai Pillbox


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Good to know





  • Sneakers or Close Toed Shoes With Traction. Leave the flip flops at home. It’s a dirt trail with some steep sections at the beginning and loose gravel. Ideally something you don’t mind getting muddy.

  • Gym Clothes. Opt for shorts over pants because it gets hot. 

  • Sunscreen and a hat. There’s not much shade.

  • Backpack for your water bottle and gear. You’ll want to have free hands to get up some of the steeper spots. 

  • A Selfie Stick is not a bad idea if you want to get a great photo of yourself on one of the graffitied pillboxes.

  • Headlamps if you plan to hike early to catch the sunrise. 

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  • Bring a backpack to hold your water bottle and gear. You’ll want to keep your hand free for the steep part. 

  • Wear sneakers. It’s a dirt trail with loose gravel that can get slippery, especially on the steep portion when you’re coming back downhill. 

  • It gets really hot midday.

  • There’s not much shade on this hike and it gets hot. Bring a hat and wear lots of sunscreen. There’s a nice breeze when you get to the top. 

  • There are no trash cans. Please take your trash out with you.



  • There is no parking lot. All of the nearby parking is in residential neighborhoods. Follow all the parking rules or you’ll definitely get a parking ticket. (No parking in the opposite direction of traffic: No parking within 4 feet of a driveway. No parking too far from the curb. No parking in the bike lane. No parking 30 feet before a stop sign, 10 feet from a fire hydrant, or 10 feet from a corner.

  • Parking will fill up during the day. If you can’t find a spot, you’ll probably end up circling for about 15-20 minutes until someone leaves. 

  • You can also park at Lanikai Beach (10 min walk away). Not a bad idea if you want to spend some time in the ocean afterwards. FYI: Lanikai has been voted one of the most beautiful beaches in the world, so needless to say, it can get crowded. Kailua Beach nearby is equally beautiful and a tad less crowded. (It’s about a 25 minute walk to the Lanikai Pillbox Hike trailhead.)


When to hike

  • This is one of the most beautiful sunrise hikes on the island. To make it to the pillboxes in time, you should start your hike at least 45 minutes before sunrise and bring a headlamp to find your way. You’ll want your hands to free on the hike, especially at the steep part.

  • Sunset hikes tend to be a little less crowded than daytime too. The sun sets on the other side (not over the ocean), but it’s still pretty.

  • Don’t attempt this hike after it’s rained. The trail can get muddy and slippery


Navigating the trail

  • Finding the trailhead. It’s on Kaelepulu Drive, directly across from the Mid-Pacific Country Club parking lot. There’s a handmade “Pillbox Trail” sign that marks the start of the hike. 

  • The trail entrance runs through private property. Stay on the trail or you might find yourself trespassing. 

  • This hike is short, but steep. The first part (about 10-15 minutes) is the steepest. There’s a rope tied to trees that you can use to help you up (or even more so on your way back down). 

  • There are 2 pillboxes. The 2nd one has the most impressive view. It only takes about 30 minutes to get to the 1st pillbox and another 10 minutes to reach the second one. From either pillbox, you can see the Mokulua Islands (The Mokes), Kailua Bay, Lanikai Beach, and Chinaman’s Hat.

  • After the 2nd pillbox, if you’d like to get a great view of the Koolau Mountain Range, continue hiking around the corner for another 20-30 minutes. There’s no incline so it’s more of a walk, than a hike.

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  • Not full on kid friendly, but we’ll call this kid friendly-ish and more for older kids. 

  • Kids will need a lot of help getting down the steep part on the return trip. 

  • Ideally you’ll have one adult per kid to help them with the steeper parts.



  • Dogs are allowed, but make sure you bring water and you may want to avoid the hottest times of day. There’s no shade and dogs have been known to get heatstroke on this hike.

  • Keep in mind that there’s a steep climb at the beginning.



  • Technically they’re bunkers, not pillboxes. What’s the difference? Pillboxes are equipped with armament, like machine guns, whereas bunkers are used for observation. In 1943, these bunkers were used for Coast Artillery observation. WW2 soldiers would sit inside and watch for enemy ships. They’d send information to artillery batteries on the Mokapu Peninsula, Kaneohe Bay Naval Air Station, and Puu Papaa. 

  • It’s also known as the Ka’iwa Ridge Trail (but most people don’t call it that).

  • In 2018, the trail was closed for 2 months for $250,000 worth of repairs to the bunkers. 

  • The twin islands off in the distance are the Mokulua Islands (aka “The Mokes). The big island is called Moku Nui and the small island is called Moku Iki.

Last Updated 9 / 19 / 21

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