The Best Pillbox Hikes on Oahu With Amazing Views

Want to do a pillbox hike on Oahu?

Oahu is full of history, including old WWII military bunkers, known as pillboxes.

Across the island Pillboxes are scattered. Many are painted with colorful designs both on the exterior and interior.

Since many of the pillboxes are in the mountains and overlook the ocean, there are quite a few great pillbox hikes.

If you want to do a pillbox hike on Oahu, here are my top picks! I was a traveling therapist who had taken assignments on Oahu for over 7 years. Hiking has been a massive passion of mine while living and working in Hawaii.

Learn More About Hawaii Travel Here: The Ultimate Hawaii Travel Guide

Lanikai Pillbox aka Kaiwa Ridge aka “The Pillbox Hike”

This hike has multiple names: Lanikai Pillbox hikes, Kaiwa Ridge, and is also informally known as The Pillbox hike.

This hike is arguably one of the most popular on Oahu for it’s beautiful views of the ocean and relatively easy trail. The views of Lanikai beach and the islands, known as mokes, are absolutely breathtaking. If you do 1 pillbox hike on Oahu, make it this one.

There are two pillboxes on the trail and they are both fairly easy to access.

While the whole ridge trail is listed as a 3.2-mile hike, you can reach the first two pillboxes in under a mile.

However, the trail is rated moderate. It has some more difficult parts to climb. When you ascend to the first pillbox, there is a steep incline that can be challenging.

There is no shade, so on hot days, it can be particularly brutal. While dogs are allowed on leash on this trail, I recommend only bringing your dog if you’re hiking at dawn or dusk and not when it’s sunny.

Sunrise is a great time to do this hike and catch a glimpse of the rising sun. You can reach the first pillbox in 20-30 minutes and the second pillbox is only a small distance away on the ridge.

Puu o Hulu or Pink Pillbox

On the west side of Oahu, the Puu o Hulu, also known as the Pink Pillbox hike, has some incredibly beautiful vistas.

This is my favorite of the pillbox hikes!

The summit of this trail overlooks the stunning blue ocean of Waianae and Electric Beach.

While there are three pillboxes on this hike, it is most known for (you guessed it) the hot pink pillbox.

The pink pillbox trail is less trafficked than the hike in Lanikai, although the trail itself is a bit more narrow and you have to be careful of your footing.

This hike is 1.6 miles and also ranked as a moderate intensity. The trek to the top could take around 30 minutes to climb.

At the top of the hike, there are three pillboxes and a thin ridgeline at the top that connects all of the pillboxes.

The trail is completely exposed to the sun and is on the hotter and drier side of the island.

Definitely prepare with adequate water and sun protection. Sunset would be the perfect time to do this hike and watch the sunset over the ocean.

Also, ensure your car has nothing visible in it while you are hiking this trail. The street parking for this trail is notorious for car break ins.

Ehukai Pillboxes

Located on the North Shore of Oahu, this pillbox hike is famous for the painted peace signs on top of the pillboxes.

There are two pillboxes on this 2.1 mile trail.

Similar to the other trails, this trail is rated moderate and is fairly easy to hike. There are a few harder sections that require steady footing.

The ground can get very muddy if it rains, so be mindful of the weather.

Different from other pillbox hikes, this trail does have shade.

The top of the trail overlooks the Banzai Pipeline on the North Shore. The breathtaking blue ocean views are photo-worthy. And the pillbox is the perfect resting place to enjoy that view.

Diamond Head

Diamond Head is the iconic mountain that sits next to Waikiki. Getting to the top of the mountain and back down is a fairly brief 1.5 mile round trip hike.

At the summit of Diamond Head, there are pillboxes and amazing views of Honolulu and the Pacific.

As of the writing of this post, you need reservations to hike Diamond Head and there’s an entry fee to get in the park/parking lot. You can learn more here.

Koko Head Crater Stairs

Koko Crater Tramway, also known as Koko Head, Koko Head Stairs, or just The Stairs, is a 1048 step climb to the top of Kokohead Lookout.

This is a challenging hike where you ascend over 1000 railroad tie stairs to the top of a mountain. By far, this is the most physically challenging hike on this list.

At the top, you’ll find multiple pillboxes with utterly breathtaking views of the Pacific and Hawaii Kai.

Read More: Koko Head Hike Hawaii: Hiking the Crater Stairs

Recap: Best Pillbox Hikes on Oahu

If you want to experience a beautiful and fun hike, check out these amazing pillbox hikes. The trails are all relatively easy, compared to other hikes on Oahu, and the views are worth the hike!