Kaiwa Ridge (Lanikai Pillbox) Trail

The Kaiwa Ridge (Lanikai Pillbox) Trail: Historic Monuments & Stunning Views Near Oahu's Lanikai Beach
Local Expert's Rating:
5.0 / 5
The Bottom Line:

Treat yourself to some of the best views on Oahu via the Lanikai Pillbox Trail, also known as the Kaiwa Ridge Trail. The most popular, short-but-steep version of this out-and-back hike brings you to some stunning ridge-top vantages overlooking the gorgeous windward coast of Oahu around Lanikai Beach.

- The HawaiianIslands.com Local Expert Team

Military bunkers, or pillboxes—many of them installed during the Second World War following Japan’s attack on Pearl Harbor—come scattered throughout the ridge crests of Oahu. In addition to provoking reflections on history, these landmarks also commonly serve up some grand views—and those available from the so-called Lanikai Pillbox Trail rank among the very best on the island!

Also known as the Kaiwa Ridge Trail, this moderately challenging, 1.6-mile (round-trip) hike shows off several historical pillboxes as well as absolutely sweeping vistas above Kailua’s celebrated Lahaina Beach. No surprise that it ranks among Oahu’s signature—and most popular—day hikes.

Separating Lahaina Beach from Keolu Hills, Kaiwa (“frigatebird”) Ridge looms sharply to above 600 feet overlooking the windward Oahu coast. The trail to the Lanikai Pillboxes takes you from residential streets up a huff-and-puff ascent to the ridgetop involving some 625 feet of elevation gain. Quite short as it is, the hike isn’t exactly easy, given its steep uphill grade and a sometimes slightly treacherous substrate. 

Speaking of, the Lanikai Pillbox/Kaiwa Ridge Trail is best tackled in dry conditions. Portions of the trail, including the main climbing portion, are quite eroded, and during or shortly after rain it can be quite slippery.

Furthermore, Kaiwa Ridge doesn’t offer much in the way of shade, so the trail gets rather brutally sun-exposed. It’s best to tackle it early in the morning or later in the afternoon or early evening.

While you can access the ridgetop pillboxes a couple of different ways, we’re describing the standard version of the hike: the out-and-back approach from the north via Kaelepulu Drive. Parking can be tricky, given the residential environment and strict parking rules. Many hikers opt to park near Lanikai Park and walk to the trailhead, which lies near the Mid Pacific Country Club. 

After the hard climb that kicks things off, the grade eases some as you come to the first bunker. Although the Lanikai Pillboxes were built in 1943, they apparently were primarily intended as observation stations rather than for armed defense. The second pillbox lies just a short way to the south of the first. Expect company at these pillboxes: people basking in the views, sure, but also posing for photos.

Those views are indeed wow-worthy, stretching from Lanikai Beach below and westward along the grooved, jagged spine of the Koolau Range offshore to the pointy twin islets of Na Mokulua, Kaneohe Bay and its toothy Mokolii islet, and, in clear conditions, Maui and Molokai.

Many turn around at the second pillbox, but there is a third one farther to the southwest along Kaiwa Ridge. It’s not necessarily as impressive a site or a viewpoint, though.

A bit demanding—and often thronged—though it is, the Lanikai Pillbox/Kaiwa Ridge Trail is certainly worth experiencing for its iconic views of windward Oahu, and, with careful supervision and caution, it’s one many young children can tackle. It’s certainly hard to beat the selfie opportunities from those pillbox vantages!

Insider Tips:
-Kaiwa Ridge offers stunning views of sunrise over Lanikai Beach. Check the current sunrise time, account for a half-hour, maybe slightly less, to reach the first pillbox, and consider scheduling an early start to experience the magic!
-If you feel like a longer trek taking in the pillboxes, it’s possible to arrange a shuttle hike traversing Kaiwa Ridge by hiking between Kaelepulu and Kamahelestreets.