• Bring a backpack to hold your water bottle and gear. You’ll want to keep your hand free for the steep part. 

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• Wear sneakers. It’s a dirt trail with loose gravel that can get slippery, especially on the steep portion when you’re coming back downhill. 

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• It gets really hot midday.

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• There’s not much shade on this hike and it gets hot. Bring a hat and wear lots of sunscreen. There’s a nice breeze when you get to the top. 

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• There are no trash cans. Please take your trash out with you.

Parking

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• There is no parking lot. All of the nearby parking is in residential neighborhoods. Follow all the parking rules or you’ll definitely get a parking ticket. (No parking in the opposite direction of traffic: No parking within 4 feet of a driveway. No parking too far from the curb. No parking in the bike lane. No parking 30 feet before a stop sign, 10 feet from a fire hydrant, or 10 feet from a corner.

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• Parking will fill up during the day. If you can’t find a spot, you’ll probably end up circling for about 15-20 minutes until someone leaves. 

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• You can also park at Lanikai Beach (10 min walk away). Not a bad idea if you want to spend some time in the ocean afterwards. FYI: Lanikai has been voted one of the most beautiful beaches in the world, so needless to say, it can get crowded. Kailua Beach nearby is equally beautiful and a tad less crowded. (It’s about a 25 minute walk to the Lanikai Pillbox Hike trailhead.)

When to hike

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• Hike early in the morning to avoid the crowds and the heat. And bonus, there are some good breakfast spots nearby (Cinnamon’s, Boots & Kimo’s, Moke’s Bread & Breakfast, etc) for an after hike meal. 

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• This is one of the most beautiful sunrise hikes on the island. To make it to the pillboxes in time, you should start your hike at least 45 minutes before sunrise and bring a headlamp to find your way. You’ll want your hands to free on the hike, especially at the steep part.

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• Sunset hikes tend to be a little less crowded than daytime too. The sun sets on the other side (not over the ocean), but it’s still pretty.

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• Don’t attempt this hike after it’s rained. The trail can get muddy and slippery

Navigating the trail

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• Finding the trailhead. It’s on Kaelepulu Drive, directly across from the Mid-Pacific Country Club parking lot. There’s a handmade “Pillbox Trail” sign that marks the start of the hike. 

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• The trail entrance runs through private property. Stay on the trail or you might find yourself trespassing. 

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• This hike is short, but steep. The first part (about 10-15 minutes) is the steepest. There’s a rope tied to trees that you can use to help you up (or even more so on your way back down). 

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• There are 2 pillboxes. The 2nd one has the most impressive view. It only takes about 30 minutes to get to the 1st pillbox and another 10 minutes to reach the second one. From either pillbox, you can see the Mokulua Islands (The Mokes), Kailua Bay, Lanikai Beach, and Chinaman’s Hat.

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• After the 2nd pillbox, if you’d like to get a great view of the Koolau Mountain Range, continue hiking around the corner for another 20-30 minutes. There’s no incline so it’s more of a walk, than a hike.