Hiking the Lanikai Pillbox Trail Back Way (Kaʻiwa Ridge) on Oʻahu
The back way up Kaʻiwa Ridge is one of the least crowded ways to hike the famous Lanikai Pillboxes, and it’s my personal favorite route to take up the ridge.
That being said, I think it’s a shame how hard the residents in Lanikai have worked to make the parking situation in neighborhood illegal, which is exactly why the back way is my preferred route.
Lanikai Pillbox Guided Tour (Main Route)
If you don’t have transportation or would like to learn about the hike from a guide, I highly recommend booking the tour below. This tour includes the price for up to four people, and the tour includes transportation from wherever you might be staying in Waikīkī.
Additionally, one of my favorite things about booking through Viator is the reserve-now-and-pay-later option. As long as you’re booking more than three days in advance, you have the option to book ahead and cancel in the future if you change your mind.
Lanikai Pillbox Back Way (Kamahele St.)
[Not a Recommended Route for Visitors]
Distance: 1.7 miles / 2.7 km
The back way is more of a locals-only route, and the only reason I’m choosing to share this information is because of the nightmare parking situation in Lanikai.
DON’T blow it up, litter, be loud, park illegally, or cause any issues that would draw negative attention to this route. Everyone, including residents and visitors alike, should try to be as respectful as possible to not draw the same amount of attention to this route as the main route in Lanikai.
Note that even though this route is longer, it’s not more difficult. The elevation gain is nearly identical as the main route, and it’s likely a shorter hike when you factor in how far you may have to walk to do the hike from the main route.
Lanikai Pillbox Trailhead Parking (Kamahele)
Parking on Kamahele St. is much easier than anywhere in Lanikai.
That being said, do not park in the cul-de-sac near the trailhead, and do not park in anyway that blocks the sidewalk or a driveway.
Other than this, parking is on Kamahele St. is much nicer in comparison, and you’ll be much closer to the trailhead compared to the main route in Lanikai.
Google Maps Directions: Lanikai Pillboxes Trailhead (Kamahele St.)
Hiking the Lanikai Pillbox Trail (Kamahele)
The hike begins up the stairs between two fences before leaving the fences behind to stay on the ridge for the rest of the way up.
Go right at the small split in the photo below to stay on the main trail.
Just after the rock in the photo below, follow the ridge to the left. This will lead up to the main Kaʻiwa ridge line, and at this point, most of the elevation gain is behind you.
Kaʻiwa Ridge
Once at the Kaʻiwa Ridge junction, go left to continue toward the Lanikai Pillboxes.
From this split, there is only another 0.3 miles (0.5 km) of relatively flat hiking to get to the second (first from this direction) and highest pillbox.
The trail to the right leads out to Wailea Point, which is the next route talked about below in this post.
Second Lanikai Pillbox
These pillboxes are numbered as if you had hiked up from the main trail in Lanikai.
The second Lanikai Pillbox is the first of two that you will come across from this direction, and the first is only a short 0.1 mile (0.2 km) walk away.
First Lanikai Pillbox
From this direction, the first Lanikai Pillbox will likely be the furthest you hike on Kaʻiwa Ridge. The rest of the trail on simply leads down to the main trail in Lanikai.
If you are interested in visiting the two famous islands offshore, read the next section.
Kayaking to the Mokulua Islands
The two islands that you see offshore from the top of Lanikai are accessible to the public by kayak only.
Kayaks can be easily reserved through the links below, and like I said earlier, one of my favorite things about booking through Viator is the reserve now and pay later option. As long as you’re booking more than three days in advance, you have the option to book in advance and cancel in the future if you change your mind.
Overall, planning both the Lanikai Pillbox Trail and a kayak tour to the Mokulua Islands is a great way to spend a full day on Oʻahu’s east side.
Lanikai Pillbox from Luika Pl. (Wailea Point)
[Not a Recommended Route for Visitors]
Distance: 2.6 miles / 4.2 km
Starting from Luika Place is likely the least practical option for most people, because of the trailhead’s location at the end of Lanikai.
However, I think this trailhead makes for a nice trail run loop if you considered running back through Lanikai to wherever you parked. This would add another 1.1 miles (1.8 km) through Lanikai to the main trailhead if you took the most direct route.
Lanikai Pillbox Trailhead Parking (Luika)
I don’t recommend parking anywhere in Lanikai. That said, walking would make for a very long journey to get to this trailhead, which is why this route is likely only practical if you’re staying in Lanikai.
Google Maps Directions: Lanikai Pillboxes Trailhead (Luika Pl.)
Hiking the Lanikai Pillbox Trail (Luika)
From Luika, there is more elevation gain and loss over the course of this route because the ridge is not as direct.
Right from the start, the trail climbs about 350 ft. (107 m) before leveling off with more mild up and downs for the rest of the hike.
The short steep section in the photo above looks worse in the photo than it actually is.
When you get to the top of the first 350-ft. (107 m) climb, turn right to head toward the pillboxes. The path the left in the second photo below leads out to Wailea Point, and it doesn’t lead to anywhere that isn’t private property.
You can’t get off of Kaʻiwa Ridge from Wailea Point.
Over the next 0.6 miles (1.0 km), the trail will go up and down slightly until the split that leads out on the ridge in the photo below.
I wanted to include this photo to tell you not to go this way. It leads onto military property, and there is no way to exit the ridge that isn’t trespassing.
From the previous split, there is only about 0.1 miles (0.2 km) more to hike to get to the split in the photo below. Stay straight on the ridge because this is the same junction that comes up from Kamahele St. in the section above.
The rest of the hike from this junction can be seen from the photos in the previous section.
Lanikai Pillbox Trail (Main Route)
If you would like to read more about the main Lanikai Pillbox Trail from the Lanikai neighborhood, check out my separate post.
Read My Separate Post: Lanikai Pillbox Trail (Kaʻiwa Ridge)
Native Plants on the Lanikai Pillbox Trail
There are nearly no native plants on the Lanikai Pillbox hike.
Generally speaking, I can always find a number of native plants on any hike, even in the most invasive areas, but the Lanikai Pillbox Trail is the exception.
Kaʻiwa Ridge is dominated by invasive grasses, Koa haole trees, and a few non-native sporadic Gaïacwood trees that cover the ridge. You have a much better opportunity to see native Hawaiian plants in down in the Lanikai neighborhood and at the beach.
On Lanikai Beach, you should very easily be able to find native plants, like Naupaka, Pōhuehue, and Maiapilo.
If you’re interested in learning more about these native Hawaiian plants, check out my post that I wrote specifically to help others find and identify Hawaiian plants across the islands.
Read My Separate Post: Native Hawaiian Plant Guide
