Lanikai Pillbox Hike: Where to Park, When to Go, What to Expect

Lanikai Pillbox HIke
Hawaii Aloha Travel > Blog > Lanikai Pillbox Hike: Where to Park, When to Go, What to Expect

The Pillbox Trail in Lanikai (or Kaiwa Ridge Trail) is my absolute favorite hike on Oahu. Today, I’m going to tell you why you should consider taking on this trek and what you need to know before you go.

The Pillbox Trail was one of the first trails I did when I moved here. When I got to the top of the mountain for the first time, the panoramic views of the island’s windward side and the Koolau Mountain Range were like nothing I had ever seen before.

I love taking visitors and new residents on this trail because it blows everyone away.

Lanikai Pillbox Hike at a Glance

Wondering if this is the right activity for you? Here are our quick facts for this fan-favorite hike:

  • Distance: 1.5 Miles Round Trip (plus additional distance to your parking spot)
  • Elevation Gain: 615 Feet
  • Difficulty: Moderate (mostly because of a steep incline and uneven terrain)
  • Location: Kailua, Oahu
Lanikai Pillbo Hike views
You can see the Koolau Mountain Range from the top of the Pillbox Trail.

Breathtaking Views

When you reach the top of the Lanikai Pillbox hike, your eyes will be drawn to the beautiful Mokulua Islands glistening in the Pacific Ocean. But don’t forget that you’ve actually got a 360-degree view. 

On a clear day, you can also see Kaneohe Bay, Waimanalo Bay, and the Makapuu Lighthouse. Turn around, and you will see the Koolau Mountain Range.

There aren’t many hikes like this, where you get breathtaking views from every angle in such a short time. This makes the Pillbox Trail a must-do for anyone who loves hiking.

The views you get along the way are pretty amazing, too. They encourage you to keep going up the mountain to see what else is in store.

Going the Distance

What I also like about this trail is that it is short enough to leave you free for the rest of your day. It’s just a few minutes from Lanikai Beach, so after you’re done, you can grab coffee and breakfast at Kalapawai Market and then head to the beach. But since the views are so stunning, you feel like you’ve done a big hike.

Along the trail, you’ll see locals with their dogs, plus tourists from all over. You know something in Hawaii is really good when you see both tourists and locals enjoying the same place.

History of Lanikai Pillbox Hike

A pillbox is a small concrete fort built partially underground. The pillboxes in Lanikai were used as observation stations during World War II. Although pillboxes are usually armed with weapons and used as defensive stations, the ones you’ll find in Lanikai held observing instruments used to determine the position of other boats.

Lanikai Pillbox Hike

Hikes in Hawaii are different from mainland hikes. They are often not paved, can get muddy from all of the rain, and are sometimes very steep as you get to the top. 

Because of this, I wanted to share my top tips for hiking the Lanikai Pillbox trail to make it enjoyable and as safe as possible. I always like to know exactly what I am getting into when I go hiking, so here are all of my tips for hiking the Pillbox Trail.

7 Things to Know Before Hiking the Lanikai Pillbox Trail

1. Go early in the morning

The trail starts out in the shade. This is deceiving because after you get to the first lookout point, the rest of the path is not shaded. So go in the morning before the sun gets super hot.
Pro tip: wear sunscreen, even early in the morning. You might not realize it, but the sun in Hawaii is intense, no matter what time of day it is.

2. There are no amenities.
Lanikai Pillbox trail is not equipped with amenities like you find in Waimea Falls, Diamond Head, or other, more touristy hikes. There is no water fountain, no bathroom, and no trash cans. Make sure you bring more water than you think you need because it gets so hot and sunny. Carry your trash out of the trail with you.
And, know that the closest public bathrooms are at Kailua Beach Park. 

Be mindful of the residents who live near the trailhead. As always, don’t leave valuables in your car.

4. Be ready for a challenge.

The short distance of this hike sometimes misleads hikers. Even though it’s only about 30 minutes to get to the top, those 30 minutes are challenging. You begin the walk with a steep climb before reaching the first lookout point. From there, the hike gets a little easier, but it is still steep.
Lanikai Pillbox is considered a moderate hike, harder than Diamond Head. If you are up for the challenge, this hike is worth doing.

5. There are two pillboxes.

After reaching the first one, stop and take it all in. It’s not much further to get to the second pillbox. From there, turn around and head back the way you came.

6. Wear sneakers or hiking boots.
I always see people trying to do this trail in flip flops, and it’s not a good idea. The unpaved path gets slippery when it’s dry and muddy when it’s been raining. I always wear my hiking boots on this trail.

7. It’s also a great place to watch the sunrise.

It’s a challenge to hike this trail in the dark before sunrise. But if you want to go, just bring a headlamp, flashlight, and a long-sleeved shirt for cooler temperatures. 

Choosing the Best Oahu Hikes

If you are considering doing the Pillbox Trail or other hikes in Hawaii, consult a local Hawaii travel agent. Our Hawaii Aloha advisors live in Hawaii and have done many of these hikes themselves. They can give you a better understanding of what the hikes entail and if they are right for you.