Best Hikes on Oahu| Lanikai Pillboxes


The Challenges of Hiking with Kids

“I’m dying! I can’t take another step. You have to (dramatic pause) carry me.” Does hiking bring out the drama in your kids? Usually, it’s my youngest, but today she charged ahead powered by her “super hiking pants”. Meanwhile, “the good hiker” dragged and moped as the gusty wind had snatched his new hat and deposited it somewhere on the other side of the mountain. Fortunately, the views were good enough to tolerate the excess whining.

One of the Best Hikes on Oahu

The Lanikai Pillbox hike (aka Kaiwi Ridge trail) is a bit of a unicorn. It’s a super short hike with stunning views – a rare and unbeatable combination. To top it off, it’s a kid-friendly hike. We’ve done this hike with babies in carriers, with toddlers, with a pack of preschoolers, and at night with headlamps. No, it’s not super easy, more of an intermediate hike. There is a bit of a scramble in the beginning and some spots are crumbly. Just watch your footing, keep the kids close, and it’s very do-able. It is a ridge hike though so if you have a runner, maybe choose to stay at sea level. That drop off is no joke.

Beauty in every direction. Now that’s a good hike.

best hikes on oahu for kids lanikai pillbox
easy hikes on oahu for kids
view from the first pillbox of lanikai pillbox trail
having a snack at the first pillbox on the lanikai pillbox trail
views from lanikai pillbox trail
Best hikes on Oahu

Don’t forget your swimsuit! Head to the beach below to jump into all that blue you were gawking at from the trail. It feels like this –

best beaches on oahu lanikai

Lanikai Pillbox Hike: Getting There

After a quick ascent through the trees, you’re instantly rewarded with ocean views. Slowly make your way up the wind-blown ridgeline to the first pillbox and take in the sweeping panorama from the Koolau mountains to the deepest blue of Kailua and Waimanalo Bays. After the first pillbox you can continue on to the nearby second, but most chose to turn around. Total hiking time is typically 40 minutes.

Want to go further? The hike continues on over rolling hills towards Waimanalo and loops back into the Lanikai neighborhood (you can see the trail line in the last hike image). The trail becomes narrower and the descent into the neighborhood is steep and tricky.

Trail Notes: The trail is exposed along its length so prepare for strong sun and wind. There is limited neighborhood parking, especially on weekends and no parking is allowed on holiday weekends. This hike is currently closed for repairs (summer 2018). Don’t fret! You can find another lovely pillbox hike with great ocean views on the north shore.

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