Guide to Hiking the Lanikai Pillbox Trail the Backway
If you’re a local looking for a quieter way to hike to the Lanikai Pillboxes, taking the backway might be just what you need. This route offers a less crowded alternative to the main trail, which allows you to enjoy the hike without the usual crowds.
While the backway is a bit longer, it’s a fun and different way to reach the pillboxes.
I want to make it clear that this trail is recommended for locals only. We all know how tough it can be to find parking around Lanikai, so I’m sharing this alternative route. But with that said, it’s important to be respectful—don’t disturb the residents, and avoid drawing attention to yourself and other hikers.
We’ve chosen not to post about this route on social media to keep it low-key. We all know how quickly things can go viral on social media, and the last thing we want is to attract unwanted attention to this neighborhood.
Note: Though officially named the Ka’iwa Ridge Trail, we’ll call it the Lanikai Pillbox Trail since that’s what most people are familiar with.
Oahu Trip Planner contains affiliate links. We may receive compensation at no extra cost to you if you purchase using one of these links. You can read our disclaimer for more information.
Lanikai Pillbox Backway Trailhead Quick Facts
Route Type: Out & back
Distance: 1.7 miles roundtrip
Duration: About 2 hours and 30 minutes
Lanikai Pillbox Trail Backway Difficulty
While the backway to the Lanikai Pillboxes is a bit longer than the main trail, it isn’t any harder. We consider both routes to be moderate in difficulty.
We noticed that the backway can feel a bit hotter with less breeze. There are also a few spots with slightly overgrown vegetation, but nothing too challenging.
Lanikai Pillbox Backway Trail Parking
Parking for the backway to the Lanikai Pillboxes can be found on Kamahele Street in the residential neighborhood. One thing I can’t stress enough is to make sure you’re parked legally. Be sure to pay attention to any posted signs.
There are also a few signs at the cul-de-sac warning against parking there—please follow them if you want to avoid a ticket and out of respect for the residents.
The good news is that parking here is much more manageable than at Lanikai for the main trail, so you should be able to find a spot without too much trouble.
What to Expect on the Trail
The hike starts at the end of the cul-de-sac, where you’ll head up the stairs. There’s a slight incline here before you reach the fence just ahead. Once you reach the fence, continue past it by heading to the left.
After this section, the hike becomes mostly steady. You’ll walk through a mix of dirt paths and rocky sections surrounded by vegetation.
As you reach this part of the trail, you’ll start to catch your first views, including the stunning Mt. Olomana, also known as Three Peaks.
You really can’t get lost on this trail. Just follow the path for a little while, and you’ll eventually reach this big rock.
After you pass the rock, make a left and continue on the trail. The views only get better from here—just take a look at the images below.
Eventually, you’ll reach the Ka’iwa Ridge junction. To stay on the trail to the pillboxes, make a left here.
The other path leads to Wailea Point, but we won’t cover that route in this article since parking is difficult there for those hiking to the pillboxes. It’s another option some hikers take instead of starting off at Kamahele Street.
From this point, you’re almost at the second pillbox, about 0.4 miles away. We’re using the term “second pillbox” because that’s how most people know it, as the main trail usually leads to the other pillbox first and then this one second. However, if you’re hiking the backway, this would technically be the first pillbox you encounter.
Soon, you’ll start seeing your first views of the Mokulua Islands in the distance.
This trail never ceases to amaze me—the views are just spectacular, which is why it’s one of my favorite hikes on Oahu. From here, the rest of the trail to the pillboxes should be straightforward.
You will then encounter another big rock on the trail close to the pillbox. Don’t worry—you can easily take the path around it, which is much easier than climbing.
You should then reach the second pillbox. This one is usually less crowded than the first, but the views are just as stunning. We typically spend some time here before walking about five minutes to reach the first pillbox—because we can’t get enough of the views.
After enjoying the first pillbox, we always turn back the same way we came since that’s where our car is parked. There’s no need to descend the main trail unless you have a ride waiting for you when you get down.
On average, it takes us about two hours to complete the hike with minimal stops.
Kayaking to the Mokulua Islands Tour
If you want to kayak to the Mokulua Islands, you can take a kayak tour there.
We recommend the one offered by Kailua Beach Adventures below. They offer both guided and self-guided options, so make sure to select the option that best suits you when booking.
Best Time to Hike the Lanikai Pillbox Trail
Our favorite time to hike the Lanikai Pillbox Trail is at sunrise. There’s nothing like watching the sunrise over the Mokulua Islands—it’s one of the best things to do on Oahu.
If the weather is good, the sunrise is absolutely stunning. Definitely at the top of our favorite sunrise spots on Oahu.
Also, since the trail is mostly open, it can get really hot in the afternoon, so I recommend starting early to beat the heat. We once tried hiking around midday, between 12:00 p.m. and 2:00 p.m., and it was just too hot. We prefer to hike before 10:00 a.m. or after 4:00 p.m. when it’s cooler.
Also, remember to bring plenty of water, wear a hat, and use sunscreen because the sun can be intense. Wearing a sun shirt is an excellent alternative if you want extra protection. Wearing proper hiking shoes with good grip is important, too, as it can get slippery after rain, and the loose dirt can be tricky even when it’s dry.
If you’re hiking the backway, keep in mind that it’s not as breezy as the main trail—we found it to be noticeably hotter on that side.