A hiker with a yellow backpack stands on a rocky trail overlooking the ocean. The view includes two small, lush islets in the distance, surrounded by vibrant turquoise water under a clear blue sky.

A Local’s Guide to Hiking the Lanikai Pillbox Trail on Oahu

ByKody B

If you’re on Oahu and looking for a hike that combines a bit of challenge with unparalleled scenic views, the Lanikai Pillbox Trail is a must-do.

As someone who’s trekked across many of Hawaii’s trails, I can confidently say that this hike stands out for its breathtaking views and unique charm. It’s not as demanding as some of the most popular hikes, like the Koko Head Trail, but it still offers spectacular views.

In this post, I’ll cover everything you need to know about the Lanikai Pillbox Trail, from what to expect and how to prepare to insider tips for making the most out of your hike.

A stunning view of the ocean from the Lanikai Pillbox Trail and coastline, with a faint rainbow arching across the sky. The horizon shows two small islets, and below, a residential area is nestled among greenery.
Would you believe me if I told you that I saw seven rainbows on one hike?

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    A hiker sits at the edge of the Lanikai pillbox on a ridge, looking out over the ocean. The scene includes two small islets in the distance and a bright blue sky above.

    Note: These images were taken at different times. Some were taken on a cloudy day, some on a rainy day, and some on a clear day with blue skies. We just wanted to show you how different the hike can be depending on the weather.

    Lanikai Pillbox Trail Quick Facts

    Difficulty: Moderate

    Distance: 1.6 miles (roundtrip)

    Elevation Gain: 613 feet

    Terrain: Dirt, steep sections

    Admission Fee: Free

    Duration: 1-2 Hours

    What to Expect When Hiking the Lanikai Pillbox Trail

    Known locally as the Kaiwa Ridge Trail, this hike is a favorite with its stunning views that span the Mokulua Islands, Lanikai Beach, Kailua Beach, and the eastern coastline of Oahu.

    While the trail is relatively short, don’t be fooled—some sections are steep and can become quite slippery following heavy rainfall. But for those willing to tackle the ascent, the panoramic views at the top are more than worth the effort.

    When you start hiking the Lanikai Pillbox Trail, you are immediately met with a steep climb. This part of the hike quickly lets you know it will be a workout. But don’t let this discourage you; the path does even out, giving you some breaks along the way with excellent lookout points.

    You will also find ropes in some sections to help you through the steeper parts. Since the trail isn’t always well-maintained, testing the ropes before you put all your trust in them is a smart idea. We use them sometimes but not always; typically more so after heavy rainfall as it can be slippery.

    The entrance to a hiking trail, marked by a sign that reads "Welcome to Kaiwa Ridge (Lanikai Pillbox)." The trailhead is surrounded by dense greenery and leads up a steep, rocky path.
    A steep and muddy section of a trail, reinforced with green mats and ropes for assistance. The trail winds through thick vegetation.
    A muddy section of the Lanikai Pillbox trail with visible footprints and a makeshift rope handrail for support. The area is dense with trees and plants, creating a shaded and slippery pathway.
    A steep dirt path with ropes along the side to aid hikers on the Lanikai Pillbox Trail, with dense foliage on either side in Oahu, Hawaii.
    A dirt trail with exposed tree roots and ropes for assistance leading through a tropical forest on the Lanikai Pillbox Hike in Oahu.
    A narrow and rugged dirt trail bordered by a chain-link fence and lush vegetation on the Pillbox Trail.

    One of the reasons why we love the Pillbox Trail is its short distance. It’s only 0.8 miles one way and it’s the perfect choice for getting out, seeing some incredible views, and not spending your entire day hiking.

    And speaking of views, about halfway up, you’ll start seeing why this trail is worth the effort. The panoramic scenes of the Mokulua Islands, Lanikai Beach, and the windward side of Oahu are absolutely stunning. No matter how many times we hike this trail, the views always take our breath away.

    As you approach the first pillbox, there’s another steep section. If you take it slow and watch your footing, you should be fine. Remember, it’s not a race to the top; it’s about enjoying the journey and beautiful scenery.

    A steep and eroded section of the Lanikai Pillbox Trail, featuring rugged terrain with exposed roots and rocky outcrops, surrounded by dense greenery.
    A challenging part of the Lanikai Pillbox Trail, showing the uneven, rocky surface of the path that winds uphill through a lush, green landscape.
    A hiker stands triumphantly at a viewpoint on the Lanikai Pillbox Trail, raising their arms with the stunning view of the Mokulua Islands and the ocean in the background.
    Hikers making their way up a narrow, grassy ridge along the Lanikai Pillbox Trail, with a clear blue sky above and lush greenery surrounding the path.
    Two hikers ascending a steep, rocky section of the Lanikai Pillbox Trail, carefully navigating the rough terrain under a bright, sunny sky.
    A hiker approaches a steep rocky outcrop on the Lanikai Pillbox Trail, surrounded by green vegetation and under a clear blue sky.
    A hiker with a yellow backpack ascends the final stretch of the Lanikai Pillbox Trail, approaching a graffiti-covered pillbox at the summit.

    Trail Safety

    Trail safety on the Lanikai Pillbox Hike is something you shouldn’t overlook. Even though it’s classified as an intermediate hike, it’s got its fair share of challenges, including some steep sections and significant drops, especially as you get closer to the top. These areas can be risky, so it’s best to steer clear of the edges to avoid accidents.

    If you’re planning to bring kids along, it’s important to keep a watchful eye on them at all times. The trail’s stunning views can easily distract, but safety should always come first, particularly when a misstep could lead to a dangerous fall.

    Related: If you are looking for an easy hike on Oahu, you can check out the Waimea Valley Trail or the Makapuʻu Point Lighthouse Trail. Both of these are perfect for families.

    Another critical piece of advice is to invest in a good pair of hiking shoes. Trust me, your ankles and feet will thank you. I’ve hiked this trail both in dry conditions and after heavy rainfall, and each time I’ve been grateful for the support and traction my hiking shoes provided.

    The trail can be unforgiving on your ankles, with uneven terrain and slippery sections that are challenging to navigate without proper footwear.

    That being said, we have seen everyone from kids to adults hiking this trail. Just make sure to know your limits and listen to your body. If you feel unsure about a section of the trail, take it slow or skip it altogether. The ultimate goal is to have a safe hike.

    A panoramic view from the top of the Lanikai Pillbox Trail, showcasing the Mokulua Islands against the backdrop of turquoise ocean waters and a clear blue sky.

    The First Pillbox

    About 20-30 minutes into your hike, you should reach the first pillbox. This spot tends to be the most popular among hikers and for a good reason. It offers a great vantage point to sit, rest, and enjoy the views.

    Depending on when you decide to tackle the trail, you might find it quite busy. Through our experiences hiking at various times, we’ve noticed it’s least crowded at sunrise or later in the day, closer to sunset. These times offer a bit of solitude and the most breathtaking views, with the early morning or late afternoon light casting a beautiful glow over the landscape.

    The first pillbox is where we like to take a breather, snack on something, and enjoy being in the moment. The view from this pillbox is nothing short of spectacular, with the vast ocean stretching out before you and the iconic Mokulua Islands off in the distance. It’s a reminder of why this trail, despite its popularity and the initial steep climb, is such a favorite amongst hikers.

    After a short rest, feeling refreshed and ready, we usually continue on to the second pillbox.

    A hiker stands on a graffiti-covered pillbox at the summit of the Lanikai Pillbox Trail, overlooking the expansive ocean and nearby islands.
    The famous pillbox on the Lanikai Pillbox Trail, covered in vibrant graffiti, with the Mokulua Islands visible in the distance against the deep blue ocean.
    A panoramic view from the Lanikai Pillbox Trail, overlooking the turquoise waters of the Pacific Ocean and the Mokulua Islands, with the town of Lanikai nestled along the shoreline.
    A hiker sits on the edge of a pillbox on the Lanikai Pillbox Trail, making a shaka hand gesture while enjoying the expansive view of the ocean and Mokulua Islands.
    A hiker dressed in a bright red outfit sits on the edge of a pillbox on the Lanikai Pillbox Trail, taking in the stunning ocean view with the Mokulua Islands in the distance.
    A rainbow arches over the ocean and the town of Lanikai as seen from the Lanikai Pillbox Trail, with lush green foliage framing the vibrant scene.

    The Second Pillbox

    The hike from the first pillbox to the second pillbox is relatively short, typically taking about 5-10 minutes. Of course, that can stretch out a bit if you’re like me and can’t resist stopping to take photo after photo.

    The second pillbox tends to be less crowded than the first. Some people decide to turn back after reaching the initial viewpoint, but if you can, we highly recommend making the extra trek. The views from the second pillbox are as stunning as from the first, offering yet another perspective on the breathtaking landscape of Oahu.

    A group of hikers stand atop a colorful, graffiti-covered pillbox on the Lanikai Pillbox Trail, with a clear blue sky and ocean in the background.
    A hiker in a red top sits on a ledge of the Lanikai Pillbox Trail, smiling with the expansive view of the ocean and Mokulua Islands below.
    A wide-angle view from the Lanikai Pillbox Trail showing the vibrant blue ocean, Mokulua Islands, and the coastal town of Lanikai under a clear sky.
    A view from the Lanikai Pillbox Trail showing the coastline, with lush green hills in the foreground and the ocean stretching out to the horizon.
    A hiker with a yellow backpack walks along the Lanikai Pillbox Trail, with the stunning view of the Mokulua Islands and the blue ocean in the distance.
    A dirt path leading up to a pillbox on the Lanikai Pillbox Trail, surrounded by green foliage and vibrant plants under a partly cloudy sky.
    A scenic view from the Lanikai Pillbox Trail, overlooking the turquoise ocean, the Mokulua Islands, and the coastal town of Lanikai, framed by a clear blue sky with scattered clouds.

    Lanikai Pillbox Sunrise

    Catching the sunrise from the Lanikai Pillbox Trail is a must-do, especially if you’re an early riser. There’s something about starting the day with a hike up to the pillboxes that sets the right tone for what’s ahead.

    The views you get as the sun rises are out of this world, easily making it one of the best spots on Oahu for a sunrise.

    We hike this trail for sunrise at least once a month, and it never gets old. It’s our favorite sunrise hike on this island and one of our top things to do on the windward side of Oahu.

    It will be dark when you start your hike, so a headlamp is key to safely navigating the trail. It also tends to be cooler in the early hours, and the breeze at the top can be pretty harsh, especially if it’s windy. You are on the Island’s windward side, so it will most likely be windy.

    Packing a light jacket is a good move to keep comfortable. We also recommend bringing some snacks with you. There’s nothing like enjoying a small bite while waiting for the sun to peek over the horizon.

    We always aim to reach the top about 15 minutes before sunrise. It gives us enough time to catch our breath, choose the best spot, and enjoy our snacks.

    The sun rises behind clouds above the Mokulua Islands, viewed from the Lanikai Pillbox Trail, casting a golden reflection on the Pacific Ocean.
    A hiker in a yellow jacket sits contemplatively on the edge of a pillbox, gazing at the clouds and ocean during sunrise on the Lanikai Pillbox Trail

    Lanikai Pillbox Sunset 

    While the sunrise hike on the Lanikai Pillbox Trail steals most of the spotlight, don’t overlook the magic of a sunset hike here. It’s a different experience, with the sun setting behind the Ko’olau Mountains, but it’s still spectacular.

    A tip for those considering the hike for sunrise or sunset: It’s a good idea to hike the trail once during the day before sunrise or sunset. This way, you will get to know the path and where to step carefully. Knowing what to expect can make your early morning or evening hike more enjoyable and safe.

    A hiker looks out over the town of Lanikai at sunset from the Lanikai Pillbox Trail, with the Koolau Mountains silhouetted against a dramatic sky.
    Taken closer to sunset
    A breathtaking view from the Lanikai Pillbox Trail, showing the turquoise waters of the Pacific Ocean, the town of Lanikai, and the rolling green hills leading to Waimanalo Beach under a clear blue sky.

    Best Time to Hike the Pillbox Trail

    Since most of the trail is exposed with minimal shade, try to avoid hiking during the midday sun, as it can make the hike uncomfortably hot.

    Starting the trail early, preferably before 10:00 am, offers the best conditions. Not only is it cooler, but the trail is also less crowded, allowing you to enjoy the peace and beauty of the hike without the bustle of too many fellow hikers.

    Afternoon hikes, especially in the heat of the day, can be challenging due to the high temperatures and direct sunlight. However, hiking towards the end of the day, around 4:00 pm or 5:00 pm, can be quite pleasant. You’ll likely find fewer people on the trail, and the temperature drops, making for a more comfortable hike.

    Also, parking can be challenging during peak hours, so keep that in mind when planning your hike.

    A panoramic view from the Lanikai Pillbox Trail, overlooking the vibrant blue ocean, the Mokulua Islands, and the lush green landscape of Lanikai, with scattered clouds in the sky.

    How to Get to the Lanikai Pillbox Trail

    The best way to get to the Pillbox Hike is to drive. We just put Lanikai Pillbox Trail, Kaelepulu Drive, Kailua in our GPS, and it takes us there. 

    It’s about a 40-minute drive from Waikiki, assuming you’re not hitting any traffic.

    If driving isn’t an option, using Uber or Lyft is a viable alternative, dropping you off closer to the trailhead than public transport.

    Taking the bus, while possible, isn’t something we recommend as you’ll end up with a 36-minute walk to the start of the trail.

    Lanikai Pillbox Parking

    Just a heads up—parking here can be hit or miss. Sometimes, the residential neighborhood is completely off-limits for parking, and other times, it’s open. To be on the safe side, we always suggest parking at Kailua Beach Park. We’ve gotten tickets a few times when we thought it was okay to park in the neighborhood but came to find out it wasn’t. Sometimes, it’s also hard to tell if the spot you are parking on is an actual parking spot.

    Parking at the Pillbox Trail can be one of the more challenging aspects of planning your hike. The parking area is in a residential neighborhood and offers limited spaces, which it shares with Lanikai Beach—a spot famed for being one of Oahu’s most beautiful beaches.

    Parking in the residential neighborhood, and the trail starts at the end of Kaelepulu Drive if you are hiking the most popular trailhead.

    If you’re a local, you can take a different route called the Lanikai Pillbox Trail backway. This trail is longer than the main one that most people use, and we only recommend it for locals.

    From our experience, the easiest times to find parking are during the early morning hours, particularly if you’re heading out for a sunrise hike. You still have a good chance of snagging a spot right after the sun rises. By about 9:30 am, however, spaces start to fill up quickly.

    Later in the day, as beachgoers head home, parking opens up again, making it easier for those planning a late afternoon/evening hike.

    It’s important to follow all parking rules closely to avoid getting a ticket. We learned this lesson the hard way after receiving a ticket when we first started hiking here. Always double-check the posted signs and ensure you’re parking legally. Here are some Hawaii parking regulations to help you out!

    Another important reminder is never to leave valuables in your car. Like many popular tourist destinations, Oahu sees its share of car break-ins, so it’s best to take all your belongings with you or leave them somewhere safe back at your accommodation.

    Also, please be considerate of the local residents. If you’re setting out early for a sunrise hike, remember that many people might still be sleeping, so keep noise to a minimum and show respect for the neighborhood.

    Tip: If the residential parking is full when you arrive, consider parking at Kailua Beach, which offers significantly more parking spots. While parking can also be hard to find at Kailua Beach, there is more space there than near the pillbox, depending on when you get there. Keep in mind, though, it’s about a 20-minute walk from Kailua Beach to the Lanikai Pillbox Trailhead.

    Street view at the corner of Aalapapa Dr and Ka’elepulu Dr in a residential area of Lanikai, Oahu, with clear skies and lush greenery surrounding the roadways.

    Street sign for Ka’elepulu Dr at the 200 block, framed by a utility pole and tropical flora under bright sunlight in Lanikai, Oahu.
    A calm street lined with parked cars for Lanikai Beach and Lanikai Pillbok Trail.

    Lanikai Pillbox Facilities

    Unfortunately, when it comes to facilities, both the Lanikai Pillbox Trail and Lanikai Beach come up short. There are no restrooms, water stations, or other amenities available at the trailhead or along the beach.

    Plan ahead before you head out—make sure you’re well-hydrated, use the restroom in advance, and bring any water or snacks you might need during your hike or beach time.

    Tips for Hiking the Pillbox Trail

    Here are some tips to help you get the most out of your Lanikai Pillbox experience:

    Wear proper shoes:  The trail can be muddy and steep, so wear sturdy shoes with good traction.

    Bring water: The trail gets hot and is not shaded, so staying hydrated is critical.

    Arrive early or later in the day: The trail can get crowded, especially on weekends and holidays. Arrive early or towards the end of the day to beat the crowds and secure a parking spot.

    Bring a light jacket if hiking for sunrise or sunset: The temperature can drop during these times, and it’s windy on this side of the island, so bring a light jacket to stay warm.

    Take your time: Enjoy the scenery and take breaks when needed. Take your time with the hike, as it’s about the journey, not just reaching the end.

    Don’t leave valuables in your car:  Unfortunately, car break-ins are not uncommon in this area. Leave valuables at home or take them with you on the hike.

    Leave only footprints: Please respect the beauty of the trail and do not litter. Make sure to pick up after yourself and try to leave the trail cleaner than you found it.

    Bring a hat and wear reef-safe sunscreen: The sun can be intense on the island, so protect your skin with a hat and reef-safe sunscreen to help preserve the ocean’s delicate ecosystem.

    Park your car legally: Do not park in front of private driveways or block traffic when parking on the street. Follow all posted signs and regulations to avoid getting a ticket. When in doubt, go park at Kailua Beach Park.

    Things to Do Near the Lanikai Pillbox Trail

    There are plenty of activities and sights to see near the Lanikai Pillbox Trail. Here are some ideas for things to do before or after your hike:

    • Relax on Lanikai Beach: After we finish the trail, we always make our way to Lanikai Beach. It’s not just a routine; it’s a perfect way to cap off the hike. Lanikai is spectacular, easily one of Hawaii’s top beaches, with stunning views and inviting waters. It’s our go-to for unwinding after the trail, offering a peaceful retreat to slow down and enjoy the gorgeous scenery.
    • Visit the nearby town of Kailua: It’s a charming place we love exploring, especially after a long hike. Walking around Kailua, we usually grab food and treat ourselves to shave ice—a perfect refreshment on a warm day. The town has a great vibe, with plenty of shops and eateries to discover.
    • Relax at Kailua Beach: If you have extra time, head to Kailua Beach for another spectacular beach on Oahu. If we can’t find parking at Lanikai Beach, we usually go to Kailua Beach because the beach there is just as impressive, with the same spectacular views of the Mokulua Islands. 

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      A man sitting in the shallow, clear waters of Lanikai Beach, Oahu, extending his arms towards the Mokulua Islands on a sunny day.

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