The Lanikai Pillboxes, or Ka’iwa Ridge Trail, is in my list of Top 3 hikes in Hawaii; the other two being Koko Head and the Kuli’ou’ou Ridge Trail. This trail has amazingly beautiful views and yet most people only hike the first portion of the trail. The “pillboxes” are old military bunkers built up on the mountain.
It starts off with a pretty steep climb up a dirt covered hill – there is no “warm-up” section on this trail, you’re just thrown right in and start sweating. At the top of the initial climb things mellow out… a little. It opens up to a nice rocky path, but has pretty much no shade, so bring your water. It’s only about 25 minutes to the first pillbox from the start of the trail.
The trail continues on, with a couple different paths to choose from. They all lead to the same location, but some paths are more difficult than others. It’s pretty easy to tell which way is easier and which way is harder, choose whatever you want depending on how much physical activity you are desiring that day. Eventually you will come to the first pillbox. The second pillbox is not that far away and is where most people stop before turning around – don’t turn around! The trail continues on and almost no one goes beyond the second pillbox so you’ll have the trail to yourself or just a few other people.
Beyond the pillboxes, the trail itself becomes even more stunning. I love the rolling green hillsides, the lone path that follows the ridge, and the peaceful tranquility. I will caution you that it does get a bit toasty as there is little shade and you’re going up and down the ridge line.
Keep following the trail until you reach the last hill. Now, it is time for the climb down. I’ve done this trail a few times and I still don’t like the climb down. For the first half, it’s fairly steep and there’s a lot of loose gravel, but there are plenty of small trees to grab onto – I recommend doing so. After about halfway down, the gravel becomes much more rocky and it’s easier to maintain your balance.
It exits about a mile from where it starts. It takes about 15 minutes to walk back, but it’s totally worth it.
Length of hike: Depends how far you go. If you stop at the second pillbox, maybe 30-40 minutes and a little less than a mile, one way. If you go all the way to the end, expect it to take about an hour and a half, plus the walk back to the car; that’s around three miles total.
Best time to go: Early in the morning, before the sun gets too high, or late afternoon. It gets pretty hot during the middle of the day since there is little shade. You can try to avoid some of the crowd by going during the week.
Worst time to go: The closer it is to noon, the hotter it gets. If it’s a holiday or weekend, expect there to be a few more people there.