After reading this Exploration Hawaii post about 5 Great Kid Friendly Trails on Oahu, our family decided to hike the Lanikai Pillboxes of Kaiwa Ridge. Though we’ve been Windward residents for years, we never hiked the Pillboxes with our young kids, instead sticking to the paved ways of Diamond Head and Makapuu Lighthouse.

Parking is tight since you’re in the cramped Lanikai area. There are a few parking stalls nearby the trail entrance, and we lucked out with a spot as hikers continually come and go. The trail entrance is nondescript, just looking like an opening between fences. Going up the Pillbox entryway is what you can expect from the rest of the hike. No paved walkways, no handrails, just dirt, rocks, and trees. Kids have a little bit of difficulty making it up, but it is very doable. Once you make it up to the landing, you’re greeted with an open view of Lanikai and the Mokulua Islands.

After admiring your first visual vista, it’s time to go up. There’s no real main path, just a general direction that all the hikers take. Some parts are wide enough for groups to pass. Other places are narrow with one lane of traffic in each direction.

On the way to the first pillbox, you have two great views. On one side, you see the Mid Pacific Country Club and on the other, Lanikai, its beaches, and the blues of the Pacific Ocean.

A word of caution. It can rain on your hike and with the wear and tear of the trail, it’ll get slick and easy to lose your footing. There was a passing drizzle on our morning hike that brought some heat relief and of course, a rainbow.

At the first pillbox, the Mokulua Islands are in clear view as well as the neighborhood of Lanikai.

The path to the second pillbox seemed more craggy and closer to ridge lines. While general caution will keep you safe, you can definitely injure yourself if you don’t respect the terrain and cooperate with fellow hikers.

From the second pillbox, you can see the entire stretch of Bellows in Waimanalo.

Sitting atop the pillbox is a great place to snack, rest, and reflect.

And of course, the panorama of the Windward coastline is just awesome.

While there are more pillboxes, the general public turns around at the second one since hiking to the others is more challenging. All in all, the hike with kids and stops along the way took under 90 minutes. After this workout, don’t forget to head to the nearby Island Snow shop for a cool, refreshing snack.

Then share your Lanikai Pillbox hike experience online with Dwellable’s #GetYourGlassOutside contest.

The Mokulua Islands while hiking Lanikai Pillboxes @Dwellable #GetYourGlassOutside pic.twitter.com/PIJbcPo0wl

— Gee Why (@geewhy) July 10, 2014

Please retweet the above tweet to help my contest entry. For a few more pictures, check out my Flickr album.

Lanikai on Dwellable