4.6
(354)
5,498
hikers
20
hikes
Hiking around Kailua, located on O'ahu's Windward side, offers diverse landscapes for outdoor enthusiasts. The region is characterized by the dramatic Ko'olau bluffs, turquoise Pacific waters, and lush rainforest interiors. Trails range from coastal paths with ocean views to challenging mountain ascents and tranquil wetland routes.
Last updated: April 27, 2026
4.9
(15)
531
hikers
2.54km
00:52
130m
130m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.9
(9)
460
hikers
2.86km
00:57
130m
130m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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4.7
(9)
72
hikers
6.69km
01:59
170m
170m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.7
(3)
66
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.7
(9)
65
hikers
6.56km
01:56
170m
170m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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The point takes its name from the fishing shrine, a natural stone formation, on the ridge above. Alāla means 'awakening' since for decades, beach houses in Lanikai were mainly used as a retreat/return to nature spot from Honolulu. However, in the 1950s, the area began to develop into a more suburban residential area.
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TRhe Lanikai Pillbox located on Ka'iwa Ridge have expansive views of the eastern coast line, Lanikai Beach down below, and Mokolua Islands just off the coast.
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The point takes its name from the fishing shrine, a natural stone formation, on the ridge above. Alāla means 'awakening' as for decades, beach houses in Lanikai were mainly used as a retreat from Honolulu. However, in the 1950s, the area began to develop into a more suburban residential area.
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The public parking lots are closed on the weekends
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This is the official Trailhead. There is no parking nearby. Best bet is to park a mile away at Kailua Beach Park.
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There is a marker up here to mark the highest point on the ridge.
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Kailua offers a diverse selection of over 20 hiking routes. These trails cater to various skill levels, from easy coastal walks to challenging mountain ascents, allowing you to explore the region's unique landscapes.
Yes, Kailua has several easy trails suitable for families. The Lanikai Pillbox No. 2 Viewpoint – Lanikai Pillbox 1 loop from Puʻuhalo is an easy 1.8-mile route known for its panoramic views. Another excellent option is the Kawainui Marsh Trail, a flat 3.5-mile path perfect for birdwatching and observing native Hawaiian wetbirds in their natural habitat.
For breathtaking vistas, the Lanikai Pillbox Hike (Kaiwa Ridge) is highly recommended, offering expansive views of the eastern coastline, Lanikai Beach, and the Mokolua Islands. The Keolu Hills Trail also provides panoramic views of the entire Kailua basin, often with fewer crowds.
Yes, the Maunawili Falls Trail is a lush rainforest trek that culminates in a hidden waterfall and a natural swimming hole. This trail offers an immersive experience into the island's verdant interior, showcasing the conservation efforts in the Maunawili Valley ecosystem.
The Olomana Three Peaks Trail, often called the 'Everest of Kailua,' is a strenuous and technical hike reserved for experienced adventurers. The Rope Scramble on Olomana Trail – Mount Olomana Summit View loop from Maunawili involves steep inclines and requires climbing with ropes in some sections, offering significant challenge and rewarding views.
The trails in Kailua are highly rated by the komoot community, with an average score of 4.7 stars from over 280 reviews. Hikers frequently praise the diverse landscapes, from stunning coastal views to lush rainforests, and the variety of trails suitable for all abilities.
Yes, many trails in Kailua are designed as loops. For instance, the popular Lanikai Pillbox 1 – Lanikai Pillbox No. 2 Viewpoint loop from Kailua is a 4.1-mile coastal ridge walk. Another option is the Lanikai Pillbox No. 2 Viewpoint – Lanikai Pillbox 1 loop from Keolu Drive + Iana Street, which is an easy 2.7-mile loop.
Kailua's trails offer a rich array of natural features. You can expect dramatic Ko'olau bluffs, turquoise Pacific waters, and the Mokolua Islands from coastal trails like the Lanikai Pillbox Hike. Inland, you'll find lush rainforests leading to waterfalls, and the Kawainui Marsh provides opportunities to observe native Hawaiian wetbirds. Notable viewpoints include Nu'uanu Pali Lookout and Tantalus Lookout.
Kailua offers pleasant hiking conditions year-round due to its tropical climate. However, the drier months from April to October generally provide more comfortable temperatures and less rain, making them ideal for exploring the trails. Even in winter, trails remain open and enjoyable, though you might encounter more rain.
While the Lanikai Pillbox Hike is very popular, the Keolu Hills Trail offers a moderate ridge hike with panoramic views of the Kailua basin, often providing a less crowded experience. The Kawainui Marsh Trail is another tranquil escape, popular with birdwatchers but generally less frequented by hikers seeking strenuous climbs.
Most public hiking trails in Kailua do not require specific permits for general access. However, it's always advisable to check local regulations or specific trail websites, especially for more remote or protected areas, as rules can change. For instance, conservation efforts in the Maunawili Valley ecosystem aim to preserve the natural corridor, and respecting trail guidelines is crucial.
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