When In Hawaii, Conquering Oahu’s Most Parking-Challenged Sunrise Hike Is A Must
The Kaiwa Ridge Trail, commonly called the Lanikai Pillbox trail, spans 0.8 miles each way with 636 feet of elevation gain to reach World War II observation posts built in 1943.
The round trip takes 60-90 minutes, with steep sections that become slippery after rain earning it an intermediate rating.
Two concrete bunkers sit 600 feet above Lanikai Beach, offering panoramic views of the Mokulua Islands and Oahu’s windward coast.
1. The Parking Challenge
Finding parking represents the trail’s biggest obstacle. Residential streets have restricted visitor parking, with no designated spots near the trailhead.
The most reliable option involves parking at Kailua Beach’s free lot and walking 15-20 minutes to the trailhead, or attempting to secure one of seven spaces near the Mid-Pacific Country Club entrance gate. Local restrictions mean parking along private residential streets creates friction with residents.
2. Trail Location and Access
The trailhead sits between private residences on Ka’elepulu Drive, directly across from Mid-Pacific Country Club. Hikers step through brush and immediately climb about 10 feet to reach the ridge trail proper.
Signage remains inconsistent, though the location becomes obvious once identified. The path consists of worn dirt, loose rocks, and mud depending on weather, with ropes installed on steeper sections that should be tested before trusting.
3. Timing and Conditions
Sunrise hikes combine cooler temperatures, smaller crowds, and optimal lighting as sun hits the Mokulua Islands.
Starting 30-40 minutes before sunrise allows time to reach viewpoints for the full experience. The trail begins in shade but offers virtually no cover after the first lookout, making early morning preferable to midday heat. Weekend mornings bring heaviest traffic, while weekday sunrise hikes provide more solitude.
4. The Two Main Pillboxes
The first observation post appears after 20-30 minutes of climbing, with the second requiring an additional 5-10 minutes.
Both structures offer photo opportunities and different perspectives on the coastline, though technically they’re observation posts rather than defensive pillboxes. The second bunker draws fewer visitors as some hikers turn back after the first. Wind along the ridge can be surprisingly strong, particularly when climbing atop the structures.
5. Safety and Preparation
Steep cliff edges lack guardrails entirely, requiring attention to footing on loose rocks and gravel. A fatality occurred on this trail, emphasizing the need for proper hiking shoes with good traction and awareness of edges.
Essential items include excessive water (more than seems necessary), sunscreen, hat, sturdy footwear, camera, and potentially a change of clothes for muddy conditions. The fully exposed trail becomes hot and humid even shortly after sunrise.
6. Alternative Transportation Methods
Forget the parking headache completely by embracing alternative ways to reach the trailhead. Ride-sharing services like Uber and Lyft operate even in early morning hours, dropping you right at the starting point without circling for parking spots.
Renting bikes from nearby Kailua town offers another fantastic option. The gentle 15-minute pedal through quiet streets provides a perfect warm-up before your climb. Plus, you’ll have no trouble securing your bike near the entrance.
For the budget-conscious, Oahu’s public bus system (TheBus) runs routes that stop within walking distance of the trailhead. Just check the schedule in advance as early morning service can be limited.
7. Pre-Hike Preparation Checklist
Packing a headlamp ranks as absolute necessity when starting this journey in darkness. The trail begins with uneven terrain and tree roots that become invisible hazards without proper lighting.
Smart hikers bring a small cushion or towel to sit on while waiting for sunrise at the top. Those concrete pillboxes get uncomfortably cold before dawn! Your camera needs protection too – the morning dew and occasional mist can damage electronics.
Water bottles might seem obvious, but many underestimate how quickly the Hawaiian sun dehydrates after it rises. Pack more than you think necessary, along with high-protein snacks to fuel your return journey.
8. Post-Hike Reward Stops
Kalapawai Market sits just minutes from the trailhead, offering the perfect celebratory breakfast after your summit adventure. Their freshly baked pastries and robust coffee provide exactly what tired hikers crave after an early morning expedition.
Lanikai Beach awaits those seeking refreshment of a different kind. Wade into the crystal-clear waters to cool off while admiring the same Mokulua Islands you just viewed from above. The perspective shift creates a satisfying completion to your morning journey.
For something more substantial, Moke’s Bread and Breakfast serves legendary lilikoi pancakes worth any wait. Their hearty portions fuel recovery and provide the perfect opportunity to relive your sunrise experience with fellow hikers.
