Oahu’s Lanikai Pillbox Hike Delivers Million-Dollar Views (free of charge)
Considered one of Oahu’s most beautiful hikes, the Lanikai Pillbox Trail is more challenging than other hikes but it’s 100% worth the effort.
Oahu is known for terrific hikes and the Lanikai Pillbox Trail is one of my favorites.
Also known as the Ka’iwa Ridge Trail, the Lanikai Pillbox Trail was originally established during World War II as a military observation post.
Today, the concrete pillboxes remain, offering hikers unparalleled views of the Mokulua Islands and the azure expanse of the Pacific.
It’s a unique blend of history and natural beauty and one of Oahu’s most beloved hiking experiences.
Note: This post may contain affiliate links. If you choose to book through these links, I receive a small commission, which I will likely blow on mai tais, poke, and shave ice. All of this internet voodoo takes place at no additional cost to you.
And while living in the posh Lanikai neighborhood will set you back a few million, this gorgeous hike is free and open to the public daily.
That’s why the Lanikai Pillbox Hike makes my list of the best FREE things to do on Oahu.
Read More: 25 Awesome Things to Do on Oahu That Won’t Cost You a Dime🌺
But this hike isn’t for everyone and I’ll get to that in a minute. First, let’s cover the stats on this trial.
Lanikai Pillbox Hike Quick Facts
| Location | Kailua (40 minutes from Waikiki) |
|---|---|
| Cost | Free |
| Parking | Free (but hard to find!) street parking |
| Hours | Trail open daily, 6am-8pm |
| Elevation & Distance | 1.8 miles roundtrip, 600-foot elevation |
| Time | Around 1-1.5 hours |
| What You’ll See | Military bunkers and Mokulua Islands 🏝️ |
A quick note about the Lanikai neighborhood
The quiet community of Lanikai is home to one of Oahu’s most stunning beaches and a pretty terrific hike. But this is, first and foremost, a residential neighborhood.
And while it’s fine for anyone to go and enjoy the hike and the beach (all beaches in Hawaii are open to the public), it’s not fine to park illegally.
So be sure not to block a driveway or mailbox and respect the serenity of the neighborhood.
This is not a “touristy” area; there are no public parking lots, just limited street parking. If you do this hike for sunrise and get there early, you won’t have much trouble finding a legal spot on the street.
Just pay close attention to the posted signs.
Or do what we usually do and just park a mile or so away at the Kailua Beach parking area and walk to the trailhead from there.
Yes, it adds some time and distance to the hike.
But it’s one of my favorite beaches on the island and after this hike, you’ll be ready for a dip in the ocean to cool off.
Best time of day for the Lanikai Pillbox Hike
All of the hikes on the windward (eastern) side of Oahu are a spiritual experience for sunrise and the Lanikai Pillbox hike is no exception.
Tip: Other good sunrise options are the Makapu’u Lighthouse Trail and Diamond Head (don’t forget you’ll need a reservation for that one!).
But unlike Diamond Head and Makapu’u, this is not a busy trail and is often more tranquil than the other two. With that said, there’s little to no shade on this trail so hike it in the mid-day heat at your own risk.
I think mid-morning between 8:00am and 10:00am – before the beachgoers take up all the good street parking and before it gets too hot – is the perfect time of day for this hike.
What to bring
There is no place nearby to buy anything so bring everything you need (and take it back out with you).
For the Lanikai Pillbox Hike, you’ll need:
- Water
- Sunscreen
- Hat
- Solid footwear. (Do not attempt this hike in flip-flops. If you squeezed actual hiking boots into your suitcase, this is the time to break them out. If not, tennis shoes with decent tread are fine.)
- Clothing with pockets for your phone and water or bring a small backpack (you’ll want your hands free for parts of this hike).
Where to find the Lanikai Pillbox Trailhead
Ok, you’ve got everything you need and you scored a place to park. Now, let’s cover how to find the trailhead.
The trailhead is located between two homes off Kaelepulu Drive, across from the Mid-Pacific Country Club & Golf Course. It’s not well marked so it’s easy to miss.
Now let’s talk about the trail itself. You may be wondering…
Is the Lanikai Pillbox Trail an Easy Hike?
While this hike is regularly listed as one of Oahu’s best easy hikes, I’m just going to say it…I don’t think this hike is easy.
(Ok fine, I did list it in my post about the best Easy Hikes on Oahu but with a few disclaimers!)
I actually consider it a moderate hike. If you’re trying to decide if you’re up to this hike, here are a few things to consider:
Would I recommend this hike for my parents? No.
Don’t get me wrong, they’re in fantastic shape. In fact, they walk 4 miles a day (that’s more than I can say!). But they’re in their 70’s and the possibility of a slip and fall on this hike is real.
Would I recommend this hike for small children? Definitely not.
Personally, I have enough trouble navigating the Lanikai Pillbox Hike myself, much less trying to guide a child safely through it.
The last time I did this one, as I was nearing the end of the trail, lowering myself down the last stretch gingerly using the safety rope, I passed a man with a baby strapped to his chest heading up.
Now, I don’t judge, but unless you’re in great shape and have done this hike before, please don’t try it with a baby strapped to you.
For grown-ups in decent shape and teenagers with sturdy shoes, this hike is fine. Just take it slowly.
Why you’ll love the Lanikai Pillbox Hike
The good news is it’s a relatively short hike.
And there are some flat areas along the way that are great for catching your breath and enjoying all those beautiful views.
And once you reach the top you can stand atop the pillboxes and enjoy amazing views of Lanikai Beach and the twin Mokulua Islands in the distance.
It’s truly a spectacular view and well worth the effort.
What’s the trail like?
The trail starts out fairly easy with plenty of shade and a gradual incline.
The rocky, gravel parts of the trail are definitely tricky to navigate in some places.
There are plenty of areas with loose dirt where you’ll need both hands free to hold onto branches or rocks as you go, especially coming back down.
I’d recommend a camelback for water so you can keep your hands free.
But if you’re just here visiting our lovely island, you probably didn’t pack a camelback. And that’s ok.
Do what I do and finish your bottle of water at the top and throw the empty in your backpack so you have your hands free on the way back down.
The Pillboxes
Once you reach the top, the trail levels out and you will enjoy incredible ocean views over Lanikai.
There are two pillboxes to see and it’s just a short hike from one to the next. This is the best part of the trail and why it’s worth the effort to get up that ridge!
Heading back down the trail
Most people will find the ascent the most challenging part of the hike just due to the steep incline.
But I think it’s more challenging on the way down because there’s a higher risk of sliding on loose rocks.
So be sure to take it slow on the way down and keep your hands free. And don’t be too proud to use that rope on the slippery part, it’s there for a reason!
Finally, here are a few more things to keep in mind anytime you’re hiking in Hawaii…
Oahu Hiking Golden Rules
Whether you’re in search of an easy hike or a more challenging Oahu hike, there are several essential guidelines that apply to all hikes in Hawaii:
1. Stay on designated trails
I cannot stress this enough. I swear, on every single hike we’ve done, we’ve seen people purposely veer off designated trails. I don’t know why people do this.
Stick to the marked trails and paths while hiking. Not only can you harm delicate ecosystems, but you’ll definitely increase the risk of an accident or rescue situation.
(You saw the sign in the picture above, right? People do get rescued off trails in Hawaii on a regular basis, don’t be one of them.)
2. Leave nothing behind
Pack out what you pack in. Bring those empty water bottles back out with you and dispose of your trash and waste. Help keep Hawaii’s natural areas pristine.
FAQs
And just in case I missed anything, here are a few of the most commonly asked questions about the Lanikai Pillbox Hike:
Do you need a reservation for the Lanikai Pillbox hike?
Nope! Unlike the Diamond Head hike, no reservation is required to hike the Lanikai Pillbox Trail.
How much time do you need for the Lanikai Pillbox Hike?
Finding a place to park could be the hardest part of this hike so be sure to allow some additional time for that.
For the hike itself, I would allow about 90 minutes so you have plenty of time to soak up all those amazing views.
What else is there to do nearby after the hike?
After the hike, head to Lanikai Beach or Kailua Beach (I think they’re equally gorgeous!).
Or have lunch in the lovely town of Kailua. You can also head over to the Byodo-In Temple or the Ho’omaluhia Botanical Gardens to round out your day.
Looking for more terrific hikes on Oahu? Start here:
The Makapu’u Lighthouse Trail: Oahu’s Best Hike for Epic Views
