Posted in Island Life

Pillboxes Hike – Kailua, HI.


Since the waves on the island are still flat (grrrr) my day off became another hiking day. Most of the more jungle-y paths were rained out, so we decided to ascend Pillboxes. Nestled in the Lanikai neighborhood of the super-wealthy, Pillboxes is a short, steep little trail that leads up to ridge-like peaks with cool, island breezes.

It’s called ‘Pillboxes’ because it was used as a defense point back in the day, so the ridge is dotted with little bunkers (a.k.a., pillboxes) Now, the bunkers are covered with bright graffiti that constantly changes – some days it’s painted completely blue or red, only to be tagged over in a few weeks. My local friend told me that he used to go to parties up in the pillboxes, since it had a crazy-good view of the stars and the moon reflecting on the beach. And probably because cops aren’t really going to catch a bunch of kids partying on top of a mountain.

I know a lot of people hate graffiti, but I’ve always loved it. And somehow, the bright colors and varied scrawl fits in perfectly with nature’s backdrop. I don’t think anyone who hasn’t been here can understand, but in Hawaii, it just makes sense.

Hike-wise, Pillboxes is unique because its 360-degree view of the eastern side of the island. You can see Lanikai Beach and the Mokes (islands) in front, the curve of the bay by Bellow’s to the right, jurassic-like Koolau mountains behind, and the span of Kailua, the North Beach Peninsula, and Chinaman’s hat to the left. And today, we could see clouds gently hovering on top of the Koolau’s casting their shadows on the housing tracs below. The turqouise water was so clear we could see the deep blue reef underneath its surface. Rumor has it that you can even see Lanikai’s resident tiger shark – estimated to be about 12-14 feet – from this vantage point on a lucky day.

Let me tell you – this hike is frickin beautiful. I truly couldn’t be any more in love with the island that I call home.














Aloha and welcome! I'm a small business owner, athlete, and mom-to-be in Honolulu, Hawaii, seeking to live the kindest and most compassionate life I can. From plant-based recipes to low-waste beauty to business lessons to travel, this blog is all things real life.

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