The Pillbox Hike, also known as the Kaiwa Ridge Trail, is one of the most picturesque and rewarding hikes in Oahu, Hawaii. This intermediate hike rises just above the beautiful Lanikai Beach, providing hikers with some of the best vistas of Oahu’s windward side.
Quick Stats
- Distance: 1 mile (1.6 km) roundtrip
- Elevation Gain: 450 feet (140 m)
- Duration: 45 – 60 mins roundtrip
- Difficulty: Easy / Moderate
What To Expect
The Pillbox Hike in Hawaii takes you on a dirt path up the Kaiwa ridge until you reach some old World War II-era concrete bunkers with panoramic views. The trail is very popular and busy, even at sunrise. There’s also very little shade, so a hat and sunscreen can be helpful.
The dirt trail has lots of sand and loose rocks that can be slippery, especially on the way down. This can get muddy after a big rain, so you’ll want to keep an eye on weather conditions before you go.
At the top of the ridge, there are amazing 360-degree views of windward Oahu. To the east, you can see Lanikai Beach and the little Mokulua islands (the ‘Mokes’), while to the west you can see the Ko’olau mountains and parts of Kailua!
How To Get To The Pillbox Hike
The trailhead for the Pillbox Hike starts in an upper-class residential neighborhood in Lanikai (a community in Kailua). It’s located on a dead-end road by a private drive, across the street from the Mid-Pacific Country Club, which is a scenic golf course in Lanikai.
Parking
There’s no dedicated parking lot for the Pillbox Hike, and it’s located in a residential area, so finding parking can be a bit tricky. It’s generally best to park somewhere in Kailua and go to the trail by walking or taking TheBus, although this does add a bit of time and the nearest bus stop is still a 5-10 minutes’ walk from the trailhead.
Safety
There’s plenty of room on this trail for kids, but make sure to steer clear of the edges because the drop-offs are pretty significant later in the hike. Hiking shoes are a much better option if you have them. There have been a few cases of people hurting their ankles on this hike and calling in an airlift.
Sunrise and Sunset Hikes: Lanikai Pillbox
The Pillbox Hike is one of the best sunrise and sunset spots on the whole island. In the morning, you’ll be watching the sun rise over the ocean (and behind the ‘Mokes’). For the sunset hike, watching the sun set behind the Ko’olau mountains is a great way to wrap up a day at Lanikai Beach.
Cost
The Pillbox Hike is FREE. There’s no ticket cost or entrance fee to do this hike.
The Pillbox Hike in Oahu, Hawaii is a must-do for any hiking enthusiast. With its stunning views, historical significance, and accessibility, it’s no wonder why it’s one of the most popular hikes in Hawaii.
Pillbox Hike Trail Guide
- Arrival: Arrive at the trailhead located in the Lanikai neighborhood. The trailhead is on a dead-end road by a private drive, across the street from the Mid-Pacific Country Club.
- Start of the Trail: The trail begins with a steep climb. You’ll notice a sign indicating the start of the Pillbox Hike. The initial climb can be a bit challenging due to the steep grade and loose dirt, but it’s short and manageable.
- First Stretch: As you ascend, you’ll be rewarded with views of the Mokulua Islands, Kailua Beach, Lanikai Beach, and the surrounding residential neighborhoods. Take your time and enjoy the scenery.
- First Pillbox: After about 20 to 30 minutes of hiking, you’ll reach the first old military pillbox bunker. This is a great spot to rest, take photos, and enjoy the panoramic views.
- Second Pillbox: From the first pillbox, continue along the ridge for another 10 minutes to reach the second pillbox. This is the usual turnaround point for most hikers.
- Optional Extended Hike: If you’re up for more adventure, you can continue along the Kaiwa Ridge Trail for about an hour. This will take you around the coast a bit farther, and finally lead you down to the residential houses located on A’alapapa Street. From there, you’ll need to walk approximately a mile back to Ka’elepupu Drive, where you first started.
- Return: Most hikers choose to return the way they came after reaching the second pillbox. Be careful as you descend, as the trail can be slippery due to loose rocks and dirt.
- Post-Hike: After your hike, consider spending some time at Lanikai Beach or Kailua Beach, both located nearby. These are some of the most beautiful beaches on Oahu and offer a great way to relax after your hike.
Remember to wear appropriate hiking shoes, bring plenty of water, and apply sunscreen. The trail can be quite exposed, and the Hawaiian sun can be intense. Enjoy your hike and the stunning views it offers!
Scott Sweeney is the creator of Virtual Hawaii 360. Scott is a professional marketer and a lifelong Hawaii enthusiast. Scott splits time between Oahu and Dayton, Ohio. In addition to his marketing endevours, he is also a published Ukulele musician.
