Lanikai Pillboxes: A Crowd Pleaser with Epic Views
- Stephen Warner
- Oct 6
- 4 min read
If you find yourself on the Windward side of Oʻahu near Kailua and ask, “What hike should I do?”, nine times out of ten someone will point you to the Lanikai Pillboxes. And there’s a good reason for that.
With a short distance, a quick reward, and stunning views over Lanikai Beach, the Mokulua Islands, and the Koʻolau Range, it’s one of the most photogenic hikes in Hawaiʻi. It’s a true bang-for-your-buck trail — just don’t expect to have it to yourself.
Trail Info
Trailhead Name | Ka'iwa Ridge Trail |
Distance (out and back) | 1st pillbox: 0.8 miles / 1.3 km 2nd pillbox: 1.0 miles / 1.6 km 3rd pillbox: 1.8 miles / 2.9 km |
Estimated time | 1-2 hours |
Elevation gain | 1st pillbox: 350 ft / 110 m 2nd pillbox: 450 ft / 140 m 3rd pillbox: 550 ft / 170 m |
Highest point | 600 ft / 183 m (Third pillbox) |
Permits / fees | None |
Parking | Street parking in Lanikai loop or near Kailua Beach Boat Ramp |
Toilets? | No |
Dog friendly? | Yes |
Know before you go
Parking is a challenge. The “Lanikai Loop” near the trailhead often has restrictions or is packed, especially on weekends. Your best bet is the Kailua Beach Boat Ramp, which adds ~30 minutes round trip to your hike but offers more reliable parking.
Most people stop at the second pillbox. That’s where you get the classic views. But continuing on toward the third offers a bit more solitude and new angles of the Koʻolaus.
The initial climb is steep and can be muddy after rain. There are a few short scrambly sections. They aren't too technical, but enough to surprise tourists expecting a casual walk.
Other trails nearby
Distance: 2.2 miles (3.5 km) out and back
Elevation gain: 650 ft (200 m) gain
Details: Located in nearby Kāneʻohe, this pillbox trail is slightly longer and usually less crowded, with sweeping views of Kāneʻohe Bay and more breathing room.
The Trail
No matter where you park, your hike starts at a break in the fence on Kaelepulu Drive. The warning signs nearby can look intimidating, but rest assured, this is a legal trail.
The climb starts immediately and steeply. After rain, this section turns into a muddy slip-and-slide, so tread carefully.
This is one of the few portions of the hike where you’ll get any shade. Soak it in if the sun’s already up.
Before long, you’ll reach the ridgeline — and from here, it’s views on views on views. The "Mokes" offshore, the turquoise water below, the green folds of the Koʻolaus. It's hard not to stop and just stare.
You’ll spot the first pillbox up ahead on the left. Just follow the rocky path upward. It's well worn and easy to follow, with a few Class 2-style sections where you’ll use your hands for balance.
There are a few sections that are minor class 2 scrambles (hands needed for balance). If you ever feel like you are doing anything too extreme, look around because there's probably an easier route nearby.
Pillbox #1 — check.
And if you’ve got a drone or you're looking down from above, this is where the beauty of this ridge really stands out.
Just a few minutes past the first pillbox is Pillbox #2 — slightly larger, with more space to sit or grab a photo.
But if you’re here during sunrise, expect to be sharing the space with a crowd of photographers and tourists.
For those wanting a little more space and a slightly longer hike, continue on to the third pillbox. Just follow the trail as it traverses the ridgeline.
Here’s a drone shot of the full ridge. We didn’t grab any photos at Pillbox #3, but the . In walk itself was more than satisfying. In fact, this hike is one of those where you don’t need a destination. Just keep walking, take it all in, and stop when you find your perfect spot.
Some trails give you views. This one feels like it is a view. Truly paradise.
SS Reflections
The Lanikai Pillbox Trail was the very first hike I did after moving to Hawaiʻi in 2016. At the time, I had only dabbled in hiking — a few treks in the Adirondacks while living in upstate New York — but I was starting to get the itch.
This trail didn’t just scratch it. It awakened something.
I remember being stunned by the color of the water, the drama of the ridge, the view of the Mokes from above. It was all so new and so ridiculously beautiful. It became the gateway trail that sparked what would become a five-year obsession: trying to hike every possible ridge, crater, and summit in Hawaiʻi.
Now, years later and living in Colorado, the landscape around me looks very different. But it’s trails like this — short, sweet, and unforgettable — that remind me where it all began.
And let’s be honest: when the views are this pretty, it’s hard not to fall in love with hiking.
Other helpful resources
The Walking Mermaid's writeup of this trail