Hawaii Hiking

Hiking Oahu: Lanikai Pillbox Trail

On our last day on the island, Logan and I decided to squeeze in one more hike; the Lanikai Pillbox trail, or otherwise known as the Kaiwa Ridge trail. Despite the overcast skies and threatening rain clouds, our guide Reid from Wanderlustyle, led us up the mountain just before sunrise.

The Lanikai Pillbox trail is one of the most famous and Insta-worthy picturesque hikes on the island. It’s located on the windward side of Oahu, above the stunning town of Kailua, and when you reach the top you will be welcomed by the best views of Lanikai beach, Kailua beach, and the Mokulua Islands.


This trail can also be tailored to beginners or more advanced hikers, depending on how far along the trail you go. It’s probably a short 30 minutes to the first pillbox and another 5-10 to the second pillbox. Most people turn around at the second pillbox and head back, however you can continue about another 30 minutes down the trail, which will take you further down the coast and lead you down to a residential area. You’ll then have to walk back to the beginning of the trail to get back to your car and what not.


Comparing the Lanikai trail to the other hikes we did on this trip, I’d have to say it’s tougher than Koko Head in terms of terrain and steep drop offs, but significantly easier than Crouching Lion. The Lanikai trail doesn’t contain any steep drop offs or sharp cliffs, so it really is perfect for all ages. The beginning of this trail is the toughest part because it’s a steep incline with a lot of loose rocks and gravel to slip on. As long as you have a buddy to help each other get over this part, you shouldn’t have too much trouble. It might seem a little intimidating at first, but rest assured, once you’re past these first 10 yards or so, it’s smooth sailing to the top; plus the trail will open up to some incredible views!


We continued on as far as the second pillbox and enjoyed the sunrise from there. It did start to rain when we got up there, so we hid from weather inside the pillbox for a bit. The second pillbox is sitting in front of the two Mokulua islands which made for some incredible sunrise photos. It’s too bad it was such a cloudy day, but it was beautiful nonetheless!

This trail wasn’t as busy as Koko Head at sunrise; I’m not too sure if the weather played a factor in that at all, but it’s something to keep in mind if you’re looking for less crowded hikes.


Time to top: 1 hour
(As I said above, to the first pillbox it’s probably about 30 minutes and an additional 10 to the second pillbox. I say one hour to give yourself enough time to get to the second pillbox as this is where most people usually end the hike. If you do decide to continue on past the second pillbox, I would add another 30-40 minutes and then keep in mind the time it will take you to walk back to your car from the residential area.)

Tips for Lanikai Pillbox Trail

  • Pack a light rain jacket. While the rain storms are never bad and never last too long, it does get windy at the top of the mountain, so you might want to have a light jacket for when it gets a little chilly.
  • Bring lots of water. Regardless of what time you go, it’s important to stay hydrated.
  • Wear sun protection. Sunscreen, a hat; make sure to protect yourself from the sun’s harmful rays!
  • Bring a flashlight. If you’re planning to hike at sunrise, definitely be sure to bring a flashlight, especially if it’s your first time. It’ll be a bit dark at the beginning of the hike, so you want to make sure you can see where you’re going, especially on those slippery rocks!
  • Don’t forget your camera! You’re going to want to make sure you can capture these views!

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