Lanikai Pill Boxes

Overlooking Lanikai from box 1


The ridge hugging the now upscale Lanikai district of the Windward side of Oahu owns a short but pleasant hike to abandoned pill-boxes that dot its summits.


  • Historical hike to World War II era bunkers used for observation of the Windward coastline front against possible Japanese invasion.
  • Short roped beginning then a dusty scramble to the ridgeline and pill boxes.
  • Ample street parking near trailhead.
  • Hot & dry: Best for overcast days. Bring lots of water.
  • Out and back style trail though continuing thru the ridgeline means ending in private property.
  • Dry and crumbly sections eventually leading to overgrown trailway.
  • FANTASTIC views of Lanikai Beach, Mount Olomana, Koolau range and other notable landmarks.
  • Family friendly hike. Continuing past the second pillbox makes the hike a bit harder.
  • 1-3 hours based on your fitness level, time spent at the top and if you continue along the ridgeline past the second bunker.


  • On hot days you can bake in the sun. Bring sunscreen and water.
  • Certain sections of this climb have steep drop offs with little vegetation to cling to though most of the trail is relatively safe.
  • Do not go into the bunkers. The ladders facilitating your entry are old and unmaintained and may not hold during your exit!
  • Proceed with caution past the second pill box and onto the ridge. The trail becomes overgrown and splits several times before meandering into confusing sections. Do not attempt to exit the end of the trail in private property.
Lanikai pillbox 1

Pill Box 1

Hiking the Lanikai Pill Box Trail

A pillbox, or military bunker, is a structure used primarily for defensive attack in warfare though the strategically positioned structures on this ridge were most definitely constructed here, high up overlooking the ocean, as posts for observation.

Several other pillbox installations are scattered throughout Hawaii with some of the more popular examples readily accessible by short, relatively easy hikes. Unquestionably the most widely known structures reside at the summit of Diamond Head Crater, a popular hike by tourists and visitors to the islands.

The Lanikai Pillbox hike begins in a somewhat rural area of Kailua, near the entrance of Mid Pacific Country club on Kaelepulu Drive.  The trailhead is well marked and beginning stretch roped with makeshift nylon roping. The hike begins up a rather eroded steep section and footing is tricky though not very dangerous.

Trailhead post

Trailhead post

The majority of this hike is very dry, unless an overnight downpour precedes your journey.  Trekking should be left for overcast and cloudy days, or in the early morning or late afternoon.

After only a short, albeit rather hefty scramble up the initial hill, the first bunker is in view.  These particular pillboxes, historically named so as they resembled the boxes used to in pill transport in the early Twentieth Century, arrive early in the hike.  Picture taking from the roof of either structure is fantastic!  ridge at Lanikai overlooks the now infamous Lanikai Beach and spreads to the southeastern head of Makapu’u, all the way eastward to China man’s hat.

Behind you is the Ko’olau Mountain Range with views from Waimanalo to Kuuloa Ranch.

roped trailhead section

roped beginning

The hike continues beyond the second pillbox but there are several options.  You can continue down the the ridge line trail and fork left to end at the other end of Lanikai, or venture right along a secondary trail and continue down thru a quiet neighborhood.  Use caution if using the latter route. The trail becomes overgrown and easy to lose. Residents are more than likely not welcoming to lost hikers, judging by the many no tresspassing signs posted.

A native cactus


  1. Tom Dwyer says:

    Street parking nearby has been limited to four vehicles, TOW AWAY Program is now in effect. If you illegally park, you will be towed!!

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