Lanikai Pillbox Hike

My holidays were filled with lots of eating and now I’m feeling the need to get out and get active.  Anyone else feeling the same?

The Lanikai Pillbox Hike, also known as the Kaiwa Ridge Trail, is a great place to get some exercise and enjoy some amazing views.  It’s a steady uphill climb and will give you a good workout, especially if you are trying to keep up with your 6 year old like I was.
The first part of the trail is the steepest and the rocks and dirt are loose, but after a bit the trail gets easier and the beautiful views begin.
This is a popular trail with people of all ages.  It’s not without it’s dangerous spots and has some high drop offs and slippery areas (we came across a lady who had slipped and was waiting for a rescue by the fire department), but with a little bit of caution it can be a safe and fun adventure for the whole family.  A few pictures can describe it better than I can so here’s an example of a steep drop-off in front of the hikers pictured:
And here’s what it looked like hiking that section.  There’s plenty of space to keep away from the edge of the drop-off.  Our 6 year old hiked the whole trail on his own and our 3 year old hiked most of it with my husband behind her holding both of her hands for support.
At the top of the trail are two pillboxes that make a great place for panoramic photos and/or a snack.  You can climb in the pillboxes and sit on top of them.  The last time we hiked this we went to both pillboxes and I think our entire adventure last about two hours which includes all the time we spent hanging out at each pillbox.  I’ve read that you can take the trail past the second pillbox and it will take you down the other end of the ridge and then you can walk back to your car on the neighborhood streets but I haven’t done that.
I’ll end this post as I began, by saying this is a great little hike if you want to get some exercise and see some amazing scenery.

Do it yourself on Oahu
Location:  The Lanikai Pillboxes are on Kaiwa Ridge which is behind the community of Lanikai.
Directions:  From Kailua, head southeast past Kailua Beach Park and the boat ramp.  Stay along the coast and head into Lanikai.  At the Y, stay to the right on Aalapapa Drive.  Then take a right on Kaelepulu Drive.  Find street parking here and then walk up the street.  Just before the road enters a gated community you’ll see a road that goes off to the left.  Take this road to the trailhead which is off the right side of this unnamed road.
Parking:  Street parking along Kaelepulu Drive.
Facilities:  No restrooms or other facilities here.
Other:  As mentioned in the post, this trail is steep and has drop-offs in some locations.  Use caution and you’ll have a fun and safe adventure.  I’d recommend taking water and wearing sunscreen.  If your kids are like mine, taking snacks will help you have happy hikers.
Cost:  Free

{ 13 comments… read them below or add one }

Cutter January 6, 2012 at 8:13 pm

We live close to this hike and do it on a regular basis. I even run it every once in a while! Just a note; the trail does continue on around to overlook Bellows Air Force Rec. base and then back down onto the Lanikai loop. From the Kailua Beach Park boat ramp, the trek is about 4 miles and is similar terrain as the hike up to the pillboxes. I have some photos from our hikes on my blog page if you are interested.
That's for keeping up you blog page with all the great info and ideas!


Oahu Mom January 6, 2012 at 11:15 pm

Thanks for the extra info!


Becky January 7, 2012 at 12:55 am

Thanks – just found your blog, great little spot. I have a 3 and 6 yr old, and will be coming to Oahu in April and think we may just check this out! Thanks, be back soon to check more out.


kailani January 9, 2012 at 7:28 am

What beautiful views! I may have to take my family there very soon!


Oahu Mom January 9, 2012 at 5:44 pm

@Becky – Glad you found this corner of the web! Hope you have a great visit in April!

@Kailani – Yes, the views are amazing!


Opa Bill January 10, 2012 at 3:14 pm

Great report! Been there, done that several times, (My Daughter lives in Kialua) enjoyed every steep step.
Pali hikes are wonderful too. Look for avocados and other fruit along the trail. Too many people think Hawai'i is only about the beaches.
PS The climb to the top of Diamond Head is fun and interesting.


Oahu Mom January 10, 2012 at 11:12 pm

@Opa Bill – Yes, we sometimes plan our Pali hikes based on what fruit is in season. :) Thanks for the reminder about Diamond Head. I haven't done that one in years.


Kate May 29, 2012 at 6:38 am


I’ve been looking for blog posts about Oahu to feature on our site. If you’re interested, you can drop me a line at Kate (at) Dwellable (.com)



jenna June 13, 2012 at 11:13 am

I am new to the island and a new mom. i appreciate your reviews on hikes and beaches and looking forward to more. would also love reviews on favorite places to eat!


Lisa July 2, 2012 at 7:11 pm

I don’t consider myself a restaurant critic by any stretch of the imagination, but I often do post about places we go out to eat. If you type ‘restaurants’ into the little search box on the right side you’ll get a list of posts on various places. Welcome to Oahu and to motherhood!


Maori whanau November 20, 2014 at 8:21 am

Thanks for awesome feedback and reviews. We are planning on doing the pillbox today and wondered if our 8yr old daughter could join us. She practically ran up and down Diamond Head so I feel confident she will handle this hike no problem. The only thing will be to ensure she stays close and safe and away from the edge.

Awesome reviews, looking forward to our next family hiking adventure :)


Fran January 21, 2015 at 9:51 pm

This is not a hike for kids under 7 years old. We went with our 4 and 2 1/2 yr old and its slippery and a steep incline. The decline was worse. If you are looking for a kid friendly hike go to Moana Falls.


Lisa February 11, 2015 at 3:06 pm

I’m sorry this hike wasn’t a fit for you and your family. I agree that it is steep and slippery in places but I think it’s hard to put an age limit on it. I think it depends on the kid. I would put a 2.5 year old in a backpack carrier for this hike but my daughter hiked this herself a few months before her 4th birthday and loved it.


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