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:


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).


How to Prepare For the Lanikai Pillbox Hike

COMFORTABLE LEGGINGS. Alo’s high waisted ones are the very best! Since I usually do this in the morning, I tend to wear pants. Click here for my favorite ones.

ATHLETIC SNEAKERS. If you’re in the market for sneakers and haven’t tried Adidas UltraBOOSTs yet you are in for a treat! They feel like you are walking on clouds. My favorite are the Stella McCartney x Adidas ones (click here for those) but the regular ones are just as good. Click here to see the latest prices.

NO-SHOW SOCKS. Ones that do not fall down! I have tried so many different ones and find that most do fall down and there's nothing worse than that while trying to hike, yah? Click here for the ones I love (they stay up!).

CUTE TOP. While I think it's incredibly important to have quality bottoms and sneakers, I find it's fine to buy cheaper workout tops because quality deos not effect you as much there. Click here for where I often find mine.

LIGHT JACKET. If you go early morning like I suggest, it can be a bit cold! DO NOT forget a light layer. Click here for where I often find mine.

BASEBALL CAP. To block the sun! Click here for the one I love for Hawaii.

SUNGLASSES. Of course! Three timeless styles I’ve been wearing non-stop: click here for my favorite Quay aviators (I have both the black and the rose gold), click here for my round Ray-Bans, and click here for my all time favorite black on black Ray-Bans that are often hard to track down because they sell out consistently.

SPF. Incredibly important, do NOT forget this. Apply it before you go. Click here for my favorite face SPF. I also always carry a mineral powder sunscreen brush with me at all times to put on top and lock in the SPF. Click here for the one I use and recommend.

REUSABLE WATER BOTTLE. Please do not forget this (and PLEASE do not buy single-use plastic ones instead). The hike is relatively easy but still tiring and you will absolutely need to bring water with you. Hydro Flask is the best because it keeps your drink cold (or warm). So worth the investment. Click here to see the latest prices.

CAMERA. You cannot hike Lanikai without bringing a camera to capture the view at the end! Click here to see the latest prices for my Sony a7II. If you don't need a full frame camera (if you aren't sure what that means, you don't need one!), I recommend the Sony a6500 instead. Click here to see the latest prices.

THE RIGHT LENS. Don't forget a wide angle lens! Click here to see the latest prices for my 35mm.

STYLISH CAMERA BAG. I never go anywhere without mine! It is incredibly important to protect your camera gear but I don’t think you should sacrifice your style to do it. Click here for my stylish camera bag roundup.

TRIPOD. If you need it to capture photos! Click here to see the latest prices for my travel tripod. Need a remote trigger too? Click here to see the latest prices.


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.



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.


The Best Tools for Traveling

Need help figuring out the rest of your trip? As a full time traveler with a LOT of experience planning trips, I have a handful of sites and tools that I cannot live without. They save me money, time, and frustration - all of which are very important for me and should be to you, too.

For flights, I use Skyscanner. Skyscanner is great because they find you the cheapest flights by comparing millions of options from airlines and travel agents. Click here to find the best flight deal!

For hotels I always use HotelsCombined, as you will notice in my recommendations. I love them because they compare all of the top travel sites in one spot - with no booking fee and no markup. Best price guarenteed! Click here to search HotelsCombined.

When I'm not staying at a hotel, I love Airbnb. When chosen right, it provides a more local experience and you can often get a lot more space for less money. Click here to get $40 off your first stay.

To get around while in city, I recommend walking, using public transit, or Uber if it's available. If you are new to Uber, use code "kbae3" to get your first ride for free. You can also use it on Uber Eats!

In larger cities or those where a rental car is needed, I recommend Avis. I personally have used nothing but Avis for the last 6+ years and have only had wonderful experiences with them. The best part? When you become a preferred member you don't even have to wait in line - you just walk off the plane and head directly to your rental car. I have also found their prices to be the best. Click here to reserve your rental.

For tours, museum tickets, and other activities, I recommend GetYourGuide. They are a trusted site and have lots of unique things to do along with all of the standard touristy activites. Booking everything individually can be a bit of nightmare to keep track of. With GetYourGuide you can create an account to book and manage all of your tickets in one central location. Click here to search GetYourGuide.

Want to stay connected while traveling? I recommend renting a pocket-sized personal WiFi hotspot from Tep! Click here to see the latest prices.


Other Helpful Hawaii Information

If you will be visiting Oahu, we have everything you need to plan your trip!

FOR WHAT TO PACKclick here for our Hawaii packing list.

FOR WHERE TO STAYclick here for the best hotels and resorts and here for the best Airbnbs.

FOR WHERE TO EAT… click here for a local’s guide to the best places to eat.

FOR WHAT TO DOclick here for my top 10 recommendations. My number one recommendation is to swim with dolphins in the wild. Click here for a detailed post about how to do that!



FOR WHERE TO HIKEclick here for Crouching Lion (my absolute favorite) and here for the Lanikai Pillboxes (my second favorite!).


Also, subscribe below to get our FREE downloadable guide and we’ll also send you some step-by-step help to plan the Hawaii trip of your dreams!


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