Pillboxes Hike



  • Wear closed toe shoes. (This hike can be done in slippers, but it’s easier in real shoes!)
  • Wear sunscreen if you’re going any time after sunrise
  • Visit on a weekday instead of a weekend to avoid heavy traffic

The pillboxes hike is a great choice if you’re looking to get a short workout, with an awesome rewarding view. The pillbox trail is located in Kailua, HI. In order to get to the hike, you’re going to want to park as close as you can to Kaelepulu Dr. This is a residential area so please be mindful of yards and posted signs regarding parking. After you park, follow Kaelepulu Dr on foot alongside the Mid- Pacific Country Club and turn left on the only opportunity you will have before the dead end!

The entrance to the hike will be straight ahead and posted. The beginning of the pillboxes hike is a steep dirt incline. Use the trees as much as you can to keep balance and avoid slipping! This part of the hike is the most difficult, and isn’t very long! After you pass this portion, the rest of the hike is a little bit of uphill hiking. You will get your heart rate up, but there aren’t any obstacles that will make this hike too difficult.

There are two pillboxes on the top that are overlooking Kailua. The first pillbox has a great view of the Mokes, and then once you venture to the second pillbox you will get a more 360 view from the top of the little pillbox hills. The trail continues downs and around the country club if wanted, or you will go back down the way that you came!

Pillbox Hike
Photo by @mlreinert24

Pillboxes is rated as medium difficulty because it is unpaved, and uphill climbing. It doesn’t take any athleticism, but   This hike doesn’t have very much coverage from the sun so bring a lot of water and apply sunscreen before you go! Sunrise from the top of pillboxes is beautiful, but I recommend that if you are going at sunrise, go on a weekday if possible! Weekends are pretty crowded as this hike is pretty easy and well known/accessible. That will give you a little more of a chance to enjoy the view in peace! This is a great morning hike, then a quick walk over to Lanikai Beach to relax.

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Note – If you’re a patient on Ideal Protein make sure bring water along with some IP friendly snacks during your hike. Also, Mangosteen or Tangerine enhancers in your water bottle will ensure that you replace any electrolytes from sweating.

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