Kailua Pillbox Hike: Breathtaking Beauty

Come to See the Beauty

The Kailua Pillbox Hike is perfect for seeing a beautiful view of Kailua Town and the beaches of both Kailua and Waimanalo. Be sure to take the time to hike it. You will get to see different types of plantlife, a very pretty view of the Mokulua Islands, and a taste of history with the pillboxes.

Who Can Hike the Trail?

I would give the hike a 2 out of 5 for difficulty, 1 being the easiest and 5 being the hardest. The hardest part is on the makai side (ocean side) in the beginning of the hike. There is a pretty steep incline there but conveniently a rope is placed around trees to help you up the trail. So pretty much anybody can hike the trail.
 

What is significant about the trail?

At the top of the Kailua Pillbox Hike, lies the pillboxes. These were built during WWII as observation points to keep an eye out for a Japanese attack. The pillboxes are left on top of the trail as reminders of the past. You can actually climb onto the top of the pillboxes and go inside! The tops of the pillboxes make a perfect place to do Yoga during the dawn of the breaking day.

Where is the trail?

You can get to the trail two ways. You can enter on Kaelepulu street next to Mid-Pacific Golf Course or Kamahele Street right before Bluestone residential area.

Kaelepulu and Aalapapa

Keolu and Kamahele

Map of the Trail


View kailua pillbox hike in a larger map

When is the Best Time to Hike the Trail?

The best time to hike the trail is dawn before the sun and midday to sunset. During the period of time between 8 a.m. and 11 a.m. the sun is directly in front of you and too strong. The sun will ruin the view of the Mokulua Islands if there are no clouds in the sky. Of course if it rains it can get dangerously muddy so exercise extra caution if there are wet weather conditions. It takes about 45 minutes to walk straight through from beginning to end. You might want to take a while to enjoy the scenery though, so plan on taking a total of one and a half to two hours to finish the whole hike.

360 View From the Top of the Pillbox

Other Pictures of the Hike

See the Koolau Mountain Range in the Distance

The Mokulua Islands... photo taken at around 8 a.m.




Notice the difference at noon




View of Enchanted Lakes (I can see my house from here)




One of the pillboxes




Earthen stairway to heaven




Trailing toward Kamahele Street




Cool plantlife. Does anyone know the name of this plant?

Hike the Trail!

Next time you're in Kailua Town make sure to hike this trail. It is an absolute must for people visiting Kailua. The hike is easy and the scenery is fantastic. So relax, clear your mind, and enjoy the nature. Oh and by the way, you will burn approximately 330 calories if you complete the whole trail. All the more reason to hike!

Also Recommended: Hiking Olomana: Three Steep Peaks