Scattered across the island of Oahu you’ll find a number of WWII military bunkers, known as pillboxes.
These concrete bunkers are frequently painted with colourful designs both inside and out and situated on mountains overlooking the ocean, which makes them the perfect hiking destination for an amazing view.
1. Lanikai Pillbox Hike (Kaiwa Ridge / The Pillbox Hike)
🚗 Distance: 1.1km
🛣 Difficulty: Moderate
The Lanikai Pillbox Hike (also known as Kaiwa Ridge Trail and The Pillbox Hike) is one of the best hikes in Oahu.
The trail is short at 1.1km out and back, taking around 30 minutes in total – depending on your fitness level.
Despite the distance, hiking to the Lanikai Pillboxes is still moderately challenging which in our opinion makes it unsuitable for younger children given the lack of shade combined with the steep and rocky terrain in certain parts.
Given the Hawaii heat and humidity, we recommend going out on this hike early morning to watch the sunrise.
The elevation gain on this hike is around 70m and once you reach the top you’ll be rewarded with panoramic views of Lanikai Beach and the North Pacific Ocean.
2. Kaena Point Pillbox Hike
🚗 Distance: 9.5 km
🛣 Difficulty: Easy/Moderate
If you’re looking for a less popular trail in Oahu, consider hiking 9.5km to the Kaena Point Pillbox.
This easy-to-moderate hike takes you along the rugged coastline and a stunning natural landscape that is almost untouched by humankind in certain places.
Expect this hike to take around two and a half hours, with some steep elevation gain and rough ground in some areas.
There is great potential to see some fantastic wildlife and marine life on this trail, including many different birds, and if you are lucky, you may spot some Hawain monk seals basking in the sun.
3. Pu’u Ma’eli’eli Trail (Pink Pillbox Hike)
🚗 Distance: 2.5 km
🛣 Difficulty: Moderate
Pu’u Ma’eli’eli (also known as the Pink Pillbox Hike), is found on the west side of Oahu just north of Waikiki.
This is one of the most popular pillbox hikes on Oahu given its iconic design, location and distance.
However, it’s still moderately difficult given the 207m elevation. As such we recommend going either early morning or late evening when the heat and humidity are lower.
There are three pillboxes along this trail, however, the second one which has been painted pink is the most iconic.
The pink colour was incepted in October 2015 as a dedication to Breast Cancer Awareness and on a clear day boasts views all the way out to Kaena Point.
It takes around 45 minutes to reach the top of the ridge, where you are rewarded with incredible views of the island and ocean below.
4. Ehukai Pillbox Hike (Peace Sign Pillbox)
🚗 Distance: 3.7 km
🛣 Difficulty: Easy/Moderate
The Peace Sign Pillbox is one of the only pillboxes which can be hiked to on the north shore of Oahu which makes it popular with tourists visiting this region of the island.
This 3.7-km loop trail starts in a residential neighbourhood with plenty of parking available and is generally considered suitable for families with children.
However, be sure to watch out for the mud as the nature of the terrain here can mean that it gets incredibly muddy and slippy after heavy rain.
You’ll find a number of walking sticks at the beginning of the trail which have been left by previous hikers.
At around the halfway point of this hike, you’ll find a picnic table, and from there it’s just a ten-minute or so stretch further to the first pillbox.
While there is a second pillbox on this trail, it’s situated on private property and therefore visiting is not recommended.
5. Makapu’u Pillbox Hike
🚗 Distance: 4 km
🛣 Difficulty: Easy
The Makapu’u Pillbox Hike is one of the most popular hikes in Oahu given both its distance and difficulty.
The trail is paved all the way to Makapuu Lighthouse and has a reasonably spread 154m incline which makes it an easy hike compared to some of the others on the island.
On the observation deck near the lighthouse, you will find the perfect spot for taking in breathtaking views.
This is a great place to visit in the winter with a chance of seeing migrating humpback whales – However, sadly during our most recent trip (January), we didn’t see any.
From the lighthouse, it’s just a short distance up a dirt path to the left of the paved trail to the pillboxes above.
Given the higher elevation of the pillboxes relative to the lighthouse, you’ll find significantly better ocean views.
Sadly there is no shade along this route, as such we highly recommend sensible clothing, sunscreen, and plenty of water.
Oahu Travel Planning Guide
🏥 Should I Buy Travel Insurance for a Trip to Oahu?
Yes, you should definitely buy travel insurance for any vacation to Oahu. Basic travel insurance coverage with Safety Wing averages between $5 – $10 per day and offers peace of mind.
🚘 Do I Need to Rent a Car for a Trip to Oahu?
I would recommend hiring a car for a trip to Oahu. Even if it’s only for a couple of days of your vacation. I personally use Discover Cars to find the best car rental deals.
However, if you are on a tight budget or you don’t plan to explore much of the island then you, then you may want to consider comparing the cost and convenience of Uber and rental cars in Oahu instead.
🏨 Where to Stay in Oahu?
The vast majority of accommodation in Oahu is located in Waikiki. If you enjoy shopping, then you may want to stay further north by the Ala Moana Shopping Mall.
Alternatively, if you’re looking to spend your vacation at the beach, then consider staying as close to Waikiki Beach as possible.