What makes the Lanikai Pillbox Hike one of the Best Hikes on Oahu?
Tackle the Lanikai Pillbox hike (aka Kaiwa Ridge trail), one of Oahu’s most spectacular treks! Picture this: you trek with your family along the slopes of the Kaiwa Ridge trail, immersing yourselves in glorious panoramic views of Oahu’s eastern coastline, including the turquoise waters of Lanikai Beach, the Mokulua Islands (also known as “The Mokes”), and the surrounding lush green landscape. The vantage points from the pillboxes provide some of the most picturesque views on the island, especially during sunrise and sunset.
The Lanikai Pillbox hike is a bit of a unicorn. It’s a super short ridge hike with stunning views – a rare and unbeatable combination. While not the easiest hike—some parts require extra caution—it’s manageable for kids who can stay close and be mindful of their steps. We’ve done this hike with babies in carriers, with toddlers, with a pack of preschoolers, and even at night to catch the moon rise.
Beauty in every direction. Now that’s a good hike.
A bit of history
The “pillboxes” themselves are World War II-era bunkers that were used by the military for observation and defense.
The Challenges of Hiking with Kids
“I’m dying! I can’t take another step! You have to (dramatic pause) carry me.” Does hiking bring out the drama in your kids? Usually, it’s my youngest, but today she charged ahead powered by her “super hiking pants”. Meanwhile, “the good hiker” dragged and moped as the gusty wind had snatched his new hat and deposited it somewhere on the other side of the mountain. Fortunately, the views were good enough to shake them out of their excessive whining.
Do your kids transform into drama kings and queens while hiking too? This Oahu gem has a way of rekindling their adventurous spirit. With manageable trails and breathtaking vistas, the Lanikai Pillbox hike is perfect for families and firmly on the list of best hikes on Oahu.
Preparing for your Lanikai Pillbox Hike
The trailhead for the Lanikai pillbox hike is located in windward Oahu about a 45 minute drive from Waikiki. Limited street parking is available in the Lanikai neighborhood (don’t park along the bike lane or block driveways and pay attention to signs because they will tow you!). The closest bathrooms are located at Kailua Beach Park.
It’s important to note that while the Lanikai Pillbox hike offers many rewards, it can get crowded, especially during peak tourist seasons. To fully enjoy the experience, it’s recommended to arrive early in the morning or later in the afternoon to avoid the heat and crowds. An early morning hike (don’t forget headlamps!) will reward you with a breathtaking sunrise over the Pacific Ocean. Similarly, the trail is popular for sunset views, offering a quieter, picturesque setting.
On the Trail – What to Expect
Begin your hike among the trees, quickly emerging to sweeping ocean views. Follow the wind-swept ridge to the first pillbox for a stunning panorama from the Koolau mountains to the deepest blue of Kailua and Waimanalo Bays. Most adventurers turn around after the second pillbox, clocking a hiking time of around 30-40 minutes.
Want to go further? The hike continues on over rolling hills towards Waimanalo and loops back into the Lanikai neighborhood (you can see the trail line in the last hike image). The trail becomes narrower and the descent into the neighborhood is steep and tricky. You can also follow the trail towards the mountains and end in the Enchanted Lake neighborhood.
A Word of Caution
The trail is exposed along its length, so prepare for strong sun and wind. And remember, this is a ridge hike, so watch out for drop-offs! There is limited neighborhood parking, especially on weekends, and no parking is allowed on holiday weekends.
Other Family Activities near the Lanikai Pillbox Hike
Local eateries nearby to fill your belly
Kailua town is the perfect stop for breakfast or lunch after your hike. There are lots of local boutiques too if you want to spend an afternoon shopping.
Over Easy. Cheery spot for creative breakfast & lunch made using local ingredients, plus cocktails. Closed Monday and Tuesday.
Kalapawai Market. A laid-back local eatery with tasty breakfast, lunch, and espresso drinks.
Best beach nears the Lanikai Pillbox Hike for a refreshing swim
Don’t forget your swimsuit! Head to the beach below to jump into all that blue you were gawking at from the trail.
Lanikai Beach. You don’t have to go far to get from the trailhead to this world-famous beach. A refresing dip is only a short walk away.
Kailua Beach. If you’re looking for a Lanikai Beach alternative, neighboring Kailua beach is just as majestic and you will find showers and bathrooms. Kalama Beach Park – in the middle of the bay – usuallally has fun waves to play in Castles Beach at the north end of Kailua Bay sometimes has surf.
Waimanalo Beach. For a wilder, bigger beach, head the opposite directions to find Waimanalo Bay Beach Park. This direction takes you the scenic way back to Waikiki.
3 Must-do Post-hike Activities
Manoa Chocolate. Stop by for a free, guided chocolate tasting with knowledgeable sommeliers.
Family Photos! Lanikai and Kailua beaches are some of my favorite spots for family photo sessions. Sometimes, families like to combine the pillbox hike with a visit tot he beach. Let me plan a fun morning so you can enjoy yourselves and take home beautiful images. Check out some favorite photo sessions in Lanikai here, here, and here.
Hey, I'm Heather
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