A vibrant view from the Lanikai Pillbox Trail backway showing a pillbox structure covered in colorful graffiti, overlooking the clear turquoise waters and the twin Mokulua Islands in the distance.

Guide to Hiking the Lanikai Pillbox Trail the Backway

ByKody B

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.

A panoramic scene from the Lanikai Pillbox Trail backway, capturing the lush green hills and the sparkling blue ocean, with the Mokulua Islands prominently visible.

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    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.

    A quiet, narrow road leading towards the Lanikai Pillbox Trail backway, lined with residential houses and lush greenery under a partly cloudy sky.
    A "No Parking Any Time" sign posted near the entrance of the Lanikai Pillbox Trail backway, surrounded by dense green foliage.

    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.

    A hiker with a bright yellow backpack ascending concrete stairs at the beginning of the Lanikai Pillbox Trail backway, surrounded by lush vegetation.
    The rugged start of the Lanikai Pillbox Trail backway, with rocky terrain leading up to a set of concrete stairs, a hiker in the distance making their way up.
    A hiker climbing up a steep, rocky section of the Lanikai Pillbox Trail backway, using both hands and feet for stability, with vegetation and a fence visible alongside the path.
    A hiker walking along a dirt path on the Lanikai Pillbox Trail backway, surrounded by tall grass and gently sloping hills under a partly cloudy sky.
    A steep and rugged section of the Lanikai Pillbox Trail backway, with a hiker navigating the rocky path near the top of a hill.

    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.

    A hiker with a yellow backpack walks along a narrow dirt trail on the Lanikai Pillbox Trail backway, surrounded by tall grass and gentle slopes under a partly cloudy sky.
    A hiker making their way up a rugged and uneven dirt path on the Lanikai Pillbox Trail, surrounded by grassy hills.
    A hiker ascends a steep, rocky incline on the Lanikai Pillbox Trail, with grass and shrubs lining the path.
    A wide view of a residential area from a higher elevation on the Lanikai Pillbox Trail, with dark clouds hovering over distant mount Olomana.
    A steep, rocky section of the Lanikai Pillbox Trail, with a hiker in the distance nearing the top, surrounded by dry vegetation.
    A close-up of a steep, eroded section of the Lanikai Pillbox Trail backway, with patches of dry grass growing on the rugged terrain.

    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.

    A woman standing on the Lanikai Pillbox Trail backway, with arms outstretched, overlooking a scenic view of the town below and distant mountains under a cloudy sky.
    A man with a yellow backpack stands on the Lanikai Pillbox Trail backway, arms wide open, gazing at the expansive view of the town and mountains below.
    A hiker on the Lanikai Pillbox Trail backway points towards the distant mountains while overlooking the town below on a cloudy day.
    A panoramic view from the Lanikai Pillbox Trail, showing distant islands and turquoise waters under a cloudy sky.
    A hiker with a yellow backpack climbs a narrow, dirt path surrounded by tall grass and bare branches on the Lanikai Pillbox Trail backway, approaching a large rock formation.
    A large, weathered boulder with a small purple flower painted on it, located on the Lanikai Pillbox Trail backway, with a hiker visible in the background.

    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.

    A hiker stands with arms outstretched on top of a large boulder on the Lanikai Pillbox Trail, overlooking the valley and town below under a cloudy sky.
    A dirt path on the Lanikai Pillbox Trail backway leads through tall, dry grass and bare branches, with a bright blue sky overhead.

    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.

    A steep, dirt section of the Lanikai Pillbox Trail surrounded by tall grass, with a hiker barely visible in the distance near the top.
    A hiker in a yellow backpack walks along a narrow dirt path on the Lanikai Pillbox Trail backway, with dry grass and bare trees under a clear blue sky.

    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.

    A panoramic view from the Lanikai Pillbox Trail backway, showing the Mokulua Islands and turquoise ocean framed by dry, bare branches.
    A view from the Lanikai Pillbox Trail, showing the coastline and turquoise waters with distant islands, framed by grassy hills.
    A hiker with a yellow backpack looking out over the Mokulua Islands and the vast blue ocean.

    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.

    A scenic view from the Lanikai Pillbox Trail, showcasing the winding trail and grassy hills leading down to the turquoise waters and the Mokulua Islands.

    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.

    A hiker with a yellow backpack walks along a narrow ridge on the Lanikai Pillbox Trail backway, with a large boulder ahead and the turquoise ocean visible in the distance.
    A narrow, rocky path on the Lanikai Pillbox Trail backway hugs a steep cliffside, with vibrant green plants and a bright blue sky above.
    A hiker climbs a rocky outcrop on the Lanikai Pillbox Trail, with the Mokulua Islands and turquoise ocean visible in the background.

    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.

    A hiker approaches a colorful, graffiti-covered pillbox on the Lanikai Pillbox Trail, set against a backdrop of clear blue skies and ocean.
    A close-up of the graffiti-covered pillbox on the Lanikai Pillbox Trail, with several people sitting on top, enjoying the panoramic ocean views.
    A clear view of the Mokulua Islands and the turquoise ocean from the Lanikai Pillbox Trail, framed by lush green foliage and a bright blue sky.

    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.

    A hiker with a yellow backpack on the Lanikai Pillbox Trail, with the clear blue ocean stretching out below.
    A steep, rocky section of the Lanikai Pillbox Trail, with lush green plants lining the path and the ocean visible in the distance.
    A vibrant view of the pillbox on the Lanikai Pillbox Trail, with several people enjoying the clear ocean views from the top, surrounded by green plants and a bright blue sky.
    A clear, unobstructed view from the Lanikai Pillbox Trail, featuring the pillbox structure covered in graffiti, with the Mokulua Islands visible in the distance.

    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.

    A view from the Lanikai Pillbox overlooking a residential area near the coast, with the ocean and two small islands visible in the distance under a clear blue sky.

    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.

    A stunning sunrise over the ocean, with the sun's reflection on the water and two small islands silhouetted against the colorful sky.

    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.

    A person sitting on the edge of the Lanikai Pillbox gazing out at the ocean and small islands below, under a partly cloudy sky.
    A panoramic view from the Lanikai Pillbox Trail showing the turquoise ocean, two small islands, and a residential area situated along the coast.

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