The Pillbox Trail in Lanikai is my absolute favorite trail on Oahu. Today, I’m going to tell you why you should consider hiking this trail 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 windward side of the island and the stunning Koolau Mountain Range were like nothing I had ever seen before.

I love taking my friends who come to visit and people who are new to the island on this trail because it blows everyone away.

About the Pillbox Trail

You will be so excited by the beautiful views of the Mokulua Islands as you look out to the water that you might forget that this trial gives you 360-degree views. Aside from the Mokulua Islands and Kailua beach, 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.

You can see the Koolau Mountain Range from the top of the Pillbox Trail.

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 that you get along the way as you climb higher and higher are pretty amazing, too. They encourage you to keep going up the mountain to see what else is in store.

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 go straight to the beach. But since the views that you get are so stunning, you feel like you’ve done a big hike.

You’ll find locals with their dogs alongside tourists along this trail. You know something in Hawaii is really good when you see both tourists and locals.

History of the Pillbox Trail

The pillboxes in Lanikai were used as observation stations in 1943. Although pillboxes are usually armed with weapons and used as defensive stations, these concrete platforms held observing instruments, which were used to determine the position of other boats.

Views of the Mokulua Islands from the top of the Pillbox Trail.

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, today I wanted to share my top tips for hiking the pillbox trail to make it enjoyable and safe. 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.

  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 trail is not shaded. This means that after the sun comes up, the trail gets very hot. The earlier in the morning you go, the less hot you will be.

    Pro tip: wear sunscreen, no matter how early in the morning it is. You might not realize it, but the sun in Hawaii is strong, no matter what time of day it is.

  2. There are no amenities.

    This 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. There is also a public restroom at the Kailua Information Center on Kailua Road.

  3. It is located in a residential neighborhood.

    Because the Pillbox Trail is located in a residential neighborhood, parking can be difficult.There is no set parking for the trail, so you have to park along the street. Be sure to respect all of the posted parking signs to avoid getting a ticket. This is another great reason to get there early in the morning.

    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 shortness 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 hike with a steep climb before reaching the first lookout point. From there, the hike gets a little easier, but it is still a steep hike.

    It is considered an intermediate hike, and it’s 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 trail gets slippery when it’s dry, and it gets 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 the sun comes up. But if you want to go, just bring a headlamp, flashlight, and a long sleeve shirt for the top. If hiking in the dark to watch the sunrise doesn’t appeal to you, check out our list of the top places to watch the Sunrise on Oahu.

If you are thinking about doing the Pillbox Trail or other hikes in Hawaii, call us. Our travel agents 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.


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