Hiking the Lanikai Pillboxes


Quite busy, and for good reason, this easy-ish 2-mile hike on the Windward side of Oahu starts under a canopy of purple flowers and leads you to not one, but TWO, pillboxes that offer sweeping views of the world-famous Mokes and bright blue waters of Kailua.

Our reason for calling this hike easy-ish?

It’s accessible and fun for the whole family, but will require a wee bit of scrambling during the steep 600 feet of elevation gain.

Don’t worry, YOU GOT THIS.

Just make sure to throw a water bottle in your pack, wear actual shoes and load up on sunscreen, because it gets hot and sunny on the unprotected ridge line.

Oh, and do me favor and treat these trails like you would the ones at home.

Scratch that.

Treat them better.

The impact the crowds have had is clear, and we want to keep this neat trail accessible for everyone in future years.

Pro Tip: Beat the crowds by continuing past the second pillbox to more single track where you’re free to frolic and sing without rubbing elbows with… well, everybody.

When To Go

You can hike this trail any time of year, though it’s recommended you get an early start to avoid crowds and find parking close by.

Getting There

This hike is located in Lanikai, near Kailua, on the Windward side of Oahu. This link in the onX Backcountry app will show you exactly how to get there. 


There’s no parking at the trailhead, so neighborhood street parking is a must – though it can be difficult to find with the popular Lanikai Beach nearby.

Click here to view a video!