This Iconic Trail Leads Hikers To Some Of The Best Views In All Of Oahu

Oahu might just be the closest one can get to heaven on this planet, given its extraordinary lush vistas, whispering coconut palms, and turquoise waves gently lapping at the shoreline. Home to the state capital, Honolulu, Oahu is commonly called "The Gathering Place," with a blend of Eastern and Western cultures and a hybrid lifestyle that reflects a sleepy surf town and a bustling island metropolis. Locals on the island spend most of their time outdoors — part of the typical Hawaiian lifestyle, marked by surfing, fishing, and hiking.

The Lanikai Pillbox Hike is a true hidden gem in Hawaii that only locals know on Oahu's Windward side. Also known as the Kaiwa Ridge Trail, it received its moniker, "The Pillbox Trail," from the military pillbox huts scattered atop the bluffs. Perfectly situated in the town of Kailua and perched right above Lanikai Beach, this trail rewards hikers with captivating views of Oahu's entire windward side, Mokulua Islands, Kailua Beach, and beyond! 

The Kaiwa Ridge Trail is one of the most popular beach hikes on the whole island. This route stands out because of its family-friendly nature and stunning panoramic views. It's a moderate-level hike, spanning 1½ miles along the coastline, and takes approximately 60 to 90 minutes to complete. Oahu is equally split between a tropical urban center and a lush, remote coastal oasis. Fortunately, the Pillbox Trail is spaced along one of the most picturesque and remote regions on Oahu.

Trailblazing the Pillbox Trail

Situated on the west side of Oahu, the Pillbox Trail promises a taste of wild, untamed wilderness away from the crowds permeating Ala Moana Center in Honolulu. Just 40 minutes from Waikiki, heading west from the center of activity on Oahu is much like entering a gateway into paradise. Life moves at a slower pace on this side of the island, and what better way to immerse yourself in island culture than in the fresh air and serenity of nature? 

The Pillbox Trail is every traveler's perfect morning outing to enjoy this spectacular island's fresh air and sunshine. For an even more exquisite experience, plan your morning workout around the sunrise and watch the first rays of the morning light soak the island in its warmth. In the summer, the sun rises as early as 5:40 a.m. If you're not an early morning person, the first light of dawn settles between 6 and 6:45 a.m. during the winter. 

The majority of the Pillbox Trail guides hikers along a gentle, consistent incline, ascending 400 feet above sea level. Hikers will reach the first pillbox after about 10 to 20 minutes and can turn around after the second pillbox, about 30 to 40 minutes into the hike. Alternatively, you can extend the route along the Kaiwa Ridge Trail, leading farther up the coastline and into residential districts along A'alapapa Street, before circling back on the back half of the loop. 

Planning the route

This pristine patch of paradise should be expected to be hard to come across without careful direction. The road to the Pillbox Trailhead is easily missed, with no street name directing visitors. Hikers beginning this trek from Waikiki will want to head east on Pali Hwy, exit at Ka'elepupu Drive, and head towards the Mid-Pacific Country Club, which this trail is directly across. When it comes to parking, hikers may want to consider parking outside the Lanikai neighborhood, as parking is limited and closely monitored by the city of Honolulu. Kailua Beach Park is an excellent alternative that only adds 20 minutes to reach the trailhead. Nearby bus routes are also available from the beach park to the start of the trail.

Although the Pillbox Trail is a short and sweet hike and encountering difficulties is rare, it's always best to know what to expect. You're almost guaranteed to leave more bronzed than before on this hike, as little shade covers the path, exposing hikers to a brilliant hazy warmth. While touring this gravel path, keep an eye out for the flourishing indigenous fauna paralleling the trail. Native koa trees, Maiapilo, and Naupaka plants add a vibrancy to the scenic landscape found only on the Hawaiian islands. If you're in the mood for a post-hike beach day, the Pillbox Trail is conveniently located next to two of Oahu's most coveted beaches: Lanikai Beach and Kailua Beach!