I’ve written about how much I love The Pillbox Trail in Kailua here and again here. It’s a short, steep hike that brings you high enough to take in 360-degree views of the windward side of Oahu and the Koolau Mountain Range. The perfect place to watch the sunrise, I always bring my friends and family up here when they come to visit. By no means “off the beaten path,” you’ll find locals walking their dogs as well as tourists along this trail. I feel like when something in a place like Hawaii is really good, there is a good mix of tourists and locals, and that’s what you get here.
So when my brother told me he wanted to do the Pillbox Trail, even though we had already hiked it together the last time he was here, I was so happy. So we got up early, got some good coffee, hiked up to the top, and spent some time just enjoying the view.
My brother decided that this is his favorite spot, too.
Some tips for the Pillbox Trail:
1. Parking is hard. The trail is in a residential neighborhood, and it starts literally behind someone’s house. There are a lot of places where parking is not allowed. You will be able to park along some of the neighboring streets. Your best bet to find parking easily is to go early in the morning.
2. There is no shade so wear sunscreen and bring plenty of water.
3. There are two pillboxes. It is worth it to get to the second hike — the views are a lot better!
4. The trail is very steep and very slippery at parts. Wear hiking shoes and be very careful.
5. Type “Pillbox Trail” into Google Maps, and you will get there without a problem.