A Guide to Hiking the Lanikai Pillbox Trail in Oahu, Hawaii

Number eight on my list of the top 10 things to do on Oahu, Hawaii is hiking, and high on my list of hikes to do is the Lanikai Pillbox hike in Kailua.  The trail leads you to two military pillboxes and one of the most beautiful views in all Oahu.

The Lanikai Pillbox trail is popular and one of my favorites because it is easy yet provides the most rewarding panoramic views.  The trail runs above my favorite beach in the whole world, Lanikai, making it the perfect morning activity before lounging around on the beach all day.

 

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HOW TO GET THERE

The Lanikai Pillbox hike, also known as the Kaiwa Ridge trail, is in Kailua on the east side of Oahu.  The trailhead can be found at 265 Kaelepulu Drive.

You cannot park at the trailhead on Kaelepulu so you’ll need to first find a spot down the street.  The most convenient place is Kaelepulu and Aalapapa but given the popularity of both this trail and the beach parking can often times be very difficult.  Find a spot anywhere you can as close to those cross streets as possible and then head up the hill to 265 Kaelepulu.

 

If you want to beat the rush and do as I do, head to Lanikai Beach for sunrise.  Watch the sun go up, get some photos, then head up to do the hike.  Once you’re done the sun will be at a good place and you can head back to the beach to lay out (or to town to grab breakfast and then back to the beach).

 

At the base of the trail you will likely see this extremely beautiful and professionally made sign marking the trailhead.  If by chance the sign is no longer there, you should notice a dirt trail (top right) heading up the mountain at 265 Kaelepulu.

 

ABOUT THE LANIKAI PILLBOX HIKE

The Lanikai Pillbox hike is a little over 1 mile in length each way and takes around 20-30 minutes each way depending on your skill level.  

 

The beginning of the trail is also the most difficult, with a super steep hill and loose dirt.  Luckily there are now ropes that you can hold onto and pull yourself up with as needed.

Definitely do not let the first five minutes discourage you - it gets much easier from here.

 

Once you get up and over the initial incline in becomes much more manageable.  You are also presented with a view of Lanikai Beach and the mokes from that point on.

 

The top of the trail has two military pillboxes.  You can also head back after the first one or keep walking for ~10 minutes to reach the second.

The trail does not loop so you'll walk back the same way you came to get down.

 

While leashed dogs are technically allowed, a sign at the trailhead warns that many dogs have died from heat exhaust so it might be best to leave your pup behind.  The majority of the trail is open and in direct sunlight so be sure to bring plenty of water for both yourself and your furry friend if you do decide to bring them along.

 

Once you are done, walk over Lanikai Beach for some well deserved rest! 

If you need food, my favorite places in the area are Kalapawai Cafe & Deli for sandwiches, Nalu Health Bar and Cafe for acai bowls, fresh juices, and smoothies, and ChadLou’s Cafe & Roastery for coffee and/or sandwiches.

 

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