A Guide to the Lanikai Pillbox Hike 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 Pillbox hike is popular and one of my favorite Oahu hikes 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.
Lanikai Pillbox Hike Oahu:
HOW TO GET TO THE LANIKAI PILLBOX HIKE
The Lanikai Pillbox hike, officially known as the Kaiwa Ridge trail, is in Kailua on the east side of Oahu. If you are looking for Honolulu hikes and have a car, this is just a short drive from the city (around half an hour). 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. Lanikai Beach parking is basically the same as the parking for this hike. 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 Oahu. 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 Lanikai Pillbox 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. It’s one of the best hikes on Oahu if you are looking for something quick and easy.
The beginning of the Pillboxes hike 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 pill box 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. See a full list of recommendations here: A Local's Guide to The Best Places to Eat on Oahu Hawaii.
For places to stay in Kailua, see 11 Best Airbnb Oahu Rentals: Waikiki, Kailua, North Shore.
HOW TO PREPARE FOR THE PILLBOX HIKE
COMFORTABLE HIKING SHOES. I used to always buy Nike sneakers until I discovered Adidas Ultraboosts. If you are in the market for new sneakers and have not tried these, they will blow your mind. It is like walking on clouds! Click here to see the latest prices.
GOOD QUALITY LEGGINGS. Because you don’t want them to be see-through when the sun hits them or to have to keep pulling them up! Alo’s high waisted ones are the best of the best (and yes, I like they much more than Lululemon’s!) and the only ones I will buy. Click here to see the latest prices.
SPF. Almost the entire trail has no shade or cover of any kind. You must wear sunblock, even in the early morning! I wear La Roche Posay’s every day of my life on my face and recommend nothing more. Click here to see the latest prices.
REUSABLE WATER BOTTLE. Do not forget this! And please don’t buy plastic toss-away ones because they are horrible for the environment. Invest in a reusable one, like my favorite Hydro Flask, for many reasons - including because it keeps your drink cold which you’ll definitely want when you hit the pillboxes at the top! Click here to see the latest prices.
CAMERA BACKPACK. To keep your camera safe, of course! I brought my favorite Christie camera backpack from GATTA. Click here to see the latest prices.