Lanikai Pillbox Hike: Oahu’s Best Ocean View

GUIDE TO THE LANIKAI PILLBOX HIKE ON OAHU

The Lanikai Pillbox hike, also known as the Kaiwa Ridge Trail, is one of the most popular hiking trails on the island. While it can be crowded, it’s worth visiting for breathtaking views of Kailua Bay, Lanikai Beach, and the Mokulua Islands (“The Mokes”). 

From the top of the trail, you can even catch a glimpse of Kaneohe Bay and the Ko’olau Mountains. Depending on the day, you may spot sea turtles or dolphins swimming in the clear waters of the ocean! 

The trail is well-maintained, but the first few sections can be steep and slick, especially after rain. Most of the hike has views of the ocean, and once you reach the top, there are two old World War 2-era pillboxes, where you’re free to hang out and enjoy the view. 

There are two different starting points for the Lanikai Pillbox hike. You’ll find very little signage in the area, but both are on Google Maps and AllTrails.com.

Entrance #1 – Lanikai Pillbox Trailhead (Most Popular & Preferred) – This trailhead starts at Kaelepulu Drive, right across from the Mid Pacific Country Club. You will see a small street leading up the mountain. When it veers left, continue straight through the bushes for about 10-20 feet, and it opens up to a more defined trail. 

Entrance #2 – Lanikai Pillbox Trailhead (Back Way/ “Locals Only”)  – The alternative route up Kaiwa Ridge starts at the end of Kamahele Street. Right before the street turns into a gated community, follow the stairs on the right-hand side up Kaiwa Ridge.

It takes 45-90 minutes to hike the Lanikai Pillbox Trail, depending on a variety of factors.

From Entrance #1 (across from the Mid Pacific Country Club), it takes 20-30 minutes to reach the first pillbox, and another 5 minutes to get to the second pillbox.

Each pillbox is only about 0.5 miles into the trailhead. You can then continue for 0.3 miles to a third, smaller stone tabletop or return to your car.

The hike is considered easy/moderate, with the most challenging climb right at the beginning. The trail is mainly loose dirt and gravel, so wear shoes with good traction (particularly if it rained a few days before your hike). 

Compared to other hikes nearby, such as the Moanalua Valley Trail, this trail is much less strenuous. 

If it’s muddy or you need extra assistance, some ropes are installed to help with the steeper sections!

Yes, the hike is kid friendly and great for families with some hiking experience together. 

There are some sections where the trail is very narrow (with no rails), so while most children can complete the hike, there are dangerous sections with steep drop-offs. Just keep an eye on them, and they should be fine. Though, you might need to carry smaller children at times. My friend’s kids, Xander and Tae, were troopers at the ages of 6 and 5:

The Lanikai Pillbox hike is an excellent choice for early risers. The sunrise over the Mokulua Islands and Kailua Bay is one of the most beautiful sights on Oahu. Plus, at just 1.7 miles round trip, you won’t have to start hiking much before dawn to reach the top by sunrise.

Be sure to arrive 45 minutes before sunrise to give yourself enough time to get to the top and secure a spot on the second pillbox for the best views. It’s also a good idea to bring a jacket for a Lanikai Pillbox sunrise hike in case it’s windy at the top.

Note: Be considerate of those who live nearby and keep noise levels down so as not to disturb them early in the morning!

The hike is on the east coast of Oahu. Therefore the sunset will be behind you, but the sky will still glow with stunning shades of pink, yellow, and blue. If you’re lucky, you may see dolphins or whales swimming in Kailua Bay.

When visiting during sunset, bringing a headlamp for the hike back down the trail is essential. A headlamp is much better than a flashlight or phone light, because there are sections of the path where you may need to use your hands.

There are three ways to get to the trailhead from your hotel in Oahu. Most travelers start in Waikiki, where 90% of Oahu’s hotel rooms are located. You can either drive or take a bus to the trailhead from Waikiki. 

However, if you are starting in Kailua, you also have the option to rent a bike. 

The drive from Waikiki to Lanikai Pillbox Trail takes about 40 minutes, depending on traffic.

Simply take Highway 1 West for 2 miles to Pali Highway 61 and continue straight onto Kailua Rd. Once you reach the beach, turn right and follow the coast for one more mile, then turn right on Kaelepulu Dr.

The best place to search for an affordable car rental in Hawaii is DiscoverCars.com. They compare local and international companies to ensure you find the best deal possible on a rental car in Oahu. 

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Parking is a downside to the Lanikai Pillbox hike. There are limited options in the nearby residential areas, but driving around you’ll eventually find one. Tickets can cost up to $200, so double-check for any “No Parking” signs. 

There are a handful of parking spots near the main entrance. If you don’t luck out there, try the additional parking spots near Lanikai Park, just a few minutes from the trailhead. 

The later in the day you arrive, the harder it will be to find a parking space. 

Taking the bus to Lanikai Pillbox Trailhead is not very convenient, and it takes over an hour to get to the trailhead. Still, it’s by far the most affordable option, at just $3-5. 

The bus route starts in Waikiki and requires a couple of transfers to get to the start of the hike: 

1. Take Oahu bus #8 or #20 from Kuhio St in Waikiki. 
2. At Ala Moana Center, you’ll need to transfer to bus #67. 
3. In downtown Kailua, transfer to shuttle bus #671. 
4. Ask the driver to drop you off at A’alapapa Drive. Then the trailhead will be just one block from there on Ka’elepupu Drive.

It is unrealistic to travel from Waikiki to the Lanikai Pillbox hike for casual travelers (over 2 hours), but the trailhead is less than 3 miles (15 minutes) from downtown Kailua.

If you want to rent a bike, Kailua Beach Adventures is a fantastic company to rent from on the windward side of Oahu. They have bicycle rentals for 4 hours, 24 hours, or one week. 

When planning to hike to the pillboxes, consider the bathroom situation … or rather … the lack thereof! There are no bathrooms along the trail.

The closest public bathrooms to the Lanikai Pillbox trailhead are at Kailua Beach Park (1.3 miles away) and the Kailua Information Visitors Center (2.2 miles away). 

So, plan ahead, and use the bathroom before you set off on the hike. 

You’ll be fine in shorts and a tee-shirt on this hike. If you’re planning to get a few hikes in on Oahu, these are the things I always pack:

• Lightweight Hiking Pants (Men/ Women) – Good to have in addition to shorts, depending on the time of year.
• Waterproof Jacket (Men/ Women) Rainfall in Hawaii can be unpredictable. A little rain is fine on a hike, but you don’t want to be drenched all day.
• Hiking Shoes (Men / Women) – These boots/hiking sneaks have good treads.
• Cell phone charger– In case your phone dies from searching for a signal, or using the flashlight after sunset.
• Hiking/Rock climbing gloves – I scoffed at this at first, then ended up using my friend’s gardening gloves on a hike! Now, I bring my own 😀
• Backpack & Bladder – Always good to bring one of these.
• Waistpack & Bladder – On longer hikes, I wear a second pack around my waist, carrying more water and a first aid kit.
• First Aid Kit – Cheap & handy.

What Were the Lanikai Pillboxes Used For?

The two main pillboxes along Kaiwa Ridge were used in WW2 as military outposts. These pillboxes were not meant to house weapons or machine guns, but instead served as lookout points. 

They were officially commissioned as Coast Artillery Observation Stations, and provided an alternative route into the mountains in case the main roads were blocked. 

The pillboxes are basically concrete bunkers constructed to provide a 360-degree view, which is still enjoyed today by hikers. Artists have spray-painted the concrete, so they’re a bit more colorful these days.

There are two pillboxes at the top of the Lanikai Pillbox hike, roughly 400 feet from one another and decorated with art and graffiti.

Each box is built into the mountain, instead of on top of it. So, you have to climb down a ladder to get inside the bunker. Most tourists just hang out on top for the best vantage point on the coastline. Xander and Tae loved the breeze and the view!

Kaiwa Ridge Trail is a beautiful and popular trail, but with increased use comes the concern of trail erosion and wear. To help protect the state’s environment and natural resources, the Department of Land and Natural Resources (DLNR) has proposed a new management plan for the trail in 2022 to improve its condition.

The plan includes surface treatments, erosion control measures, fencing or other barriers, and trail signage throughout the corridor to make it safer for visitors and healthier for the land. 

The DLNR also encourages visitors to follow Leave No Trace principles and be mindful of the impact your presence has on the environment.

You’ll definitely notice the wear constant hiking has on the trail.

Hiking Lanikai Pillbox is one of the best hikes on Oahu, but many hikers have similar questions before they visit for themselves. Here are some of the most frequently asked questions.

Is the Lanikai Pillbox hike Legal?

Yes, the trail is completely legal, even though there are no bathrooms or signs for the trailhead.

This is a valid question, since Oahu’s famous “Stairway to Heaven” has been off-limits for years. Granted, people still break the local ordinance and hike the old staircase, but you run the risk of encounters with guards, and fines from police.

🌎 Jared’s Detours BLOG: Hike Stairway to Heaven the *Legal Way*

There are no laws against bringing your drone to Hawaii and flying it recreationally.

However, drones are not permitted to fly from the Lanikai Pillbox trail. There’s a law against flying drones less than 400 feet from private property.

If you’d like to get a birds-eye view of the Lanikai area, you can fly your drone from the beach all the way out to the Mokes!

Are Dogs and Pets Allowed?

Yes, pets are allowed on the Kaiwa Ridge trail, but your dogs must be kept on a leash.

Is there a Cost to Hike / Do you Need a Permit for Lanikai Pillbox?

Technically, you are supposed to purchase a permit from the state parks website for $2.50, but this requirement is not enforced.

So, the hike is almost entirely free, unless you get a fine for parking in a “no parking zone.” 

What is Kailua Known For?

Kailua is a famous beach town on the windward side of Oahu. It’s known for its laid-back vibe, beautiful beaches, and stunning scenery, making it a great day trip from Waikiki.

Is Lanikai Beach Open to the Public?

Yes, Lanikai Beach is open to the public and free to access for both tourists and locals.  Be courteous as you drive around the neighborhood looking for a spot to park.

Xander and Tae are regulars at Lanikai:

Post Lanikai Hike Activities

After hiking the Lanikai Pillbox Trail, there are plenty of other activities and attractions in Kailua.

a Nalu Bowl!

There are lots of great restaurants and shops near the Lanikai Pillbox trailhead, but one of the best spots to get a bite to eat is Nalu. 

They specialize in Açaí bowls, smoothies, salads, Hawaiian coffee, and other healthy dishes to help you refuel from the hike.  I’d recommend a bowl, plus the turkey sandwich 😋

Visit Lanikai Beach

At the top of the Lanikai Pillbox hike, you’ll get a view of one of the most beautiful beaches in Hawaii. Lanikai beach is a great spot for swimming and sunbathing. Plus, it’s much less touristy and far less crowded than other beaches closer to Waikiki.

Hike Diamond Head

Diamond Head is another short hike on Oahu, right next to Waikiki Beach. It’s probably the most popular hike on the island and easy to complete in a short time.  I like the view from Lanikai Pillbox better, but Diamond Head delivers views of Honolulu and Waikiki:

Where to Stay on Oahu

The Waikiki area, depending on traffic, is about a 40 to 45 minute drive to Kailua. You can use this interactive map to plug in your dates and search around for rentals and hotels: