Lanikai Pillbox Hike / Kaiwa Ridge Trail

Phone (808) 587-4175
4.5 stars from 9 reviews
Address 357 Kaelepulu Dr, Kailua, HI 96734
Popular hike that pays off with some amazing views at the top.

• General: Cost: Free • General: Photo Opportunity
• Hiking: Hiking • Hiking: Length: 1-2 Miles
• Hiking: Level: Easy • Hiking: Level: Moderate
• Hiking: Major Elevation Changes • Hiking: Out & Back Trail
• Hiking: Ridge Hike • Hiking: Rock Climbing
• Sightseeing: Great Views

Matt Anderson's Take
The Lanikai Pillbox Hike, which is also known as the Kaiwa Ridge Trail, is a 1.6 mile long (each way), out and back style hiking trail in the Kailua area of O'ahu. This is a hugely popular trail with locals and tourists alike.

Because it's so popular and the parking situation is lacking (welcome to Hawaii!) it may be tough to find a place to park. Going early is your best bet and look for legal parking on Kaelepulu Drive. Make sure you don't park where the signs forbid it. This will also be the best time to avoid the heat.

Bring plenty of water for everyone and wear good shoes as parts of the trail can be muddy and slippery at times. It's an uphill climb pretty much the whole way. The steepest and usually slipperiest parts are in the beginning. As always, be sure to read Hiking Safety & Essentials before heading out and apply sunscreen to Protect Yourself From Sunburn & Skin Cancer as the trail is completely exposed.

While this is an easy trail for many, it still has plenty of dangers and areas where you can slip and fall. Easy is a relative term as well. It's short, but you'll climb in elevation very fast so it's like a big stairway to the top.

Of course, the stairs are just compressed dirt trails and loose dirt and rocks so it's easy to slip. Easy does not mean a walk in the park so this isn't for everyone. In fact, while many bring kids on this trail we don't suggest doing that. There are places where a fall will be very serious, possibly even deadly for keiki (kids).

But, if you just want to hike to the first pillbox then you're really only looking at about a 0.5 mile hike up (and the same back down) with around a 380 foot elevation gain which is far more manageable and what many people do. This is why most consider this an easy hike. Continue on and you're looking at overall elevation gains around 600 feet.

When you reach the top you'll find the pillboxes that give this trail its common name. These are a great place to snap some amazing pictures since you can climb on top of them and enjoy incredible views of Lanikai Beach.

I'd avoid this if it is raining or just rained. If it's windy outside it will be worse as you go up. Certain areas are pure ridge with steep falls on both sides so wind won't help if you're not comfortable with heights.
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Matt Anderson
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Matt A
Joined: Feb 2013
Reviews: 803
Likes Received: 111
The views are a 5 for sure but the hike itself isn't my favorite. It's not terribly long or difficult, though it will work out your legs a bit, but also just not that exciting for my tastes. It's still worth doing because the views at the top are truly incredible. Unless heights bother you, in which case you'll want to skip this one.

I see a lot of people bringing really tiny kids on this hike but there is a real fall danger here and so I can't imagine bringing little ones on this trail. I also saw several couples with babies either in a backpack carrier or just held which is nuts. One slip and your baby will get hurt, maybe killed. Why risk that?
Kerrie R
Joined: Sep 2016
Reviews: 44
Likes Received: 0
This hike is not for faint hearted, this is such a hard hike, we got up really early and headed up for sunrise. We thought we were fit, however, this was not a walk in the park, I was ok, however, we did have to take a couple of stops. A word or advice, take it one step at a time. It is worth it when you get to the top. Time Lapse the sunrise/sunset - something that you just have to do - The Views are absolutely sensational! Definitely worth it!
Jordan T
Joined: May 2016
Reviews: 17
Likes Received: 0
I went here like before the sunrise and we got a beautiful view of the sunrise but I didn't have my camera at this time so I couldn't get the pictures I wanted. I wish I had my camera so I could post what I saw and you guys could see what I saw at that time.
Tom T
Joined: Sep 2013
Reviews: 579
Likes Received: 33
This hike is best enjoyed early. It's gets crowded after 8am. It's easy to access - not too challenging. The steepest part is at the beginning.

There are 2 pillboxes, but there isn't anything particularly spectacular about them. The inside walls are vandalized with spray painted graffiti, which is a shame but not unexpected. I wouldn't make the effort to crawl inside the pillbox and pretend to play war. gross.

The views from Lanikai Pillbox are amongst the most spectacular in Oahu. Overlooking Lanikai, and the the islets offshore, it's just a magical place to sit and enjoy the view. But go early and avoid the traffic jam on the way up.
Debra F
Joined: Mar 2016
Reviews: 12
Likes Received: 0
You better be in good shape to hike up all these stairs. No stopping and it is one way. But a good experience.
Consensus Guy
Joined: Jul 2013
Reviews: 11148
Likes Received: 26
This is a hugely popular trail and most agree that it is on the easier side though still has challenges with drop offs and some slippery areas you have to climb. Many kids will love those but smaller kids need to be supervised if they go.

Some of the latest reviews seem to complain that the trail has eroded a bit (especially the beginning part) and that the parking situation is pretty bad.

Still, the vast majority seem to love this hike and the amazing views it provides.
Jewel A
Joined: Mar 2014
Reviews: 24
Likes Received: 16
This hike is famous! The best place to take photos with the turquoise clear water of Lanikai beach, and the Mokulua Islands in the back. We went around 1:30 pm and it was way too hot! Parking wasn't a problem since it was the that of the day. We could not breathe, and the breathtaking views didn't help. Lol. But we just kept moving forward on what looked like the great walk of Hawaii (like Great Wall of China)!

Next time I'm wearing a bikini top and shorts. You hit a couple plateaus and see the BEAUTIFUL water. The mornings are always better to hike places anyway, and the sunrise would be unreal if you were up on those ridges. There's a lot of dirt, and desert like grass so sometimes I thought I was in Arizona, but then the view is a million bucks and more. That water and small islands made me feel like I was in the Caribbean or some other island (Maybe, I don't know, Hawaii! Lol)it was so amazing. But the pillbox is nice. I just laid down and took pictures. Hawaii is beautiful!

@Jessica M, the filthiness and nasty stench may have just been from a night before. I went and it was all cleaned up with no smell. I don't think it's like that all the time. Sorry you had to experience that though!
Jessica M
Joined: Mar 2014
Reviews: 7
Likes Received: 4
I hiked Lanikai Pillbox with my family and it was really fun. It's an easy hike, so it's the perfect time for first-time hikers. The view from the pillboxes is amazing. The view of the ocean never ceases to take my breath away.

The only thing I disliked about this hike was the filthiness of the pillboxes. I was really excited to take photos inside with the famous graffiti room, but nobody ever mentioned all of the trash lying around inside the pillbox. It didn't smell too good either.
Joined: Apr 2014
Reviews: 3
Likes Received: 3
It’s known for being one of Oahu’s easiest hikes. There are 2 pillboxes. It approximately takes 30 minutes to hike to the farthest pillbox. Parking can be quite crowded, especially on the weekends. I recommend going on a weekday. If you must go on a weekend try to go the earliest as possible. It can get really hot and feel like it’s a long never ending hike, but really it’s not.

This hike is breathtaking, you can’t help but take pictures. It has amazing views of Lanikai and Kailua. As you walk up the hill you will love the view of the ocean. When you reach the first pillbox it will feel like you are flying. I enjoy climbing on the top of the pillbox, but be careful getting down and don’t get too close to the edge. I recommend just hanging out at the first pillbox to enjoy the view, relax, and take pictures. When you’re done resting look to the right and you should see the second pillbox. It’s not too far away. This is the peak of the hike. When you get to the pillbox the view will take your breath away.

Bring a lot of water so you won't get dehydrated in the heat. It’s a really fun hike and was the first hike I've done on the island of Oahu. Try this out to start off if you are a beginner hiker. It’s worth a try, you won’t regret the amazing views.
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