Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Hikes
United States
Honolulu County

Kailua

The best walks and hikes around Kailua

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.

Best hiking trails around Kailua

  • The most popular hiking route is Lanikai Pillbox No. 2 Viewpoint – Lanikai Pillbox 1 loop from Puʻuhalo, an easy 1.8 miles (2.9 km) trail that takes 56…

Last updated: April 27, 2026

4.9

(15)

531

hikers

#1.

Lanikai Pillbox No. 2 Viewpoint – Lanikai Pillbox 1 loop from Lanikai

2.54km

00:52

130m

130m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Navigate with device

Send to Phone

Save

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
Sign up for free to see 16 more hikes around Kailua.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Close

Loading

Popular around Kailua

Running Trails around Kailua

Road Cycling Routes around Kailua

Cycling around Kailua

MTB Trails around Kailua

Tips from the Community

Christopher
October 16, 2023, Alālā Point

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.

0

0

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.

0

1

Christopher
October 8, 2023, Alālā Point

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.

0

0

Meitapu
July 4, 2023, Lanikai Beach

The public parking lots are closed on the weekends

Translated by Google

0

0

This is the official Trailhead. There is no parking nearby. Best bet is to park a mile away at Kailua Beach Park.

0

0

There is a marker up here to mark the highest point on the ridge.

0

0

a short hike past the first.

0

0

Short steep hike to first pillbox

0

0

Frequently Asked Questions

How many hiking trails are available around Kailua?

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.

Are there any easy, family-friendly hikes in Kailua?

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.

Which trails offer the best viewpoints in Kailua?

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.

Are there any hikes in Kailua that lead to waterfalls?

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.

What are some challenging hikes for experienced adventurers in Kailua?

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.

What do other hikers enjoy most about the trails in Kailua?

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.

Are there any circular hiking routes in Kailua?

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.

What kind of natural features or landmarks can I expect to see while hiking in Kailua?

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.

What is the best time of year to go hiking in Kailua?

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.

Are there any trails in Kailua that are less crowded than the popular spots?

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.

Are there any specific permits required for hiking certain trails in Kailua?

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.

Most popular routes around Kailua

Running Trails around Kailua

Most popular attractions around Kailua

Places to see

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Explore more

Browse the best Hikes in other regions.

Urban HonoluluRound Top Forest ReserveEast HonoluluHanauma Bay State ParkKoko Head Regional ParkWaimaluHickam HousingWaimanalo BeachHickam Air Force BaseWaipioWaimanaloWaikeleWaipahuRoyal KuniaMililani TownWaipio AcresMililani MaukaAieaHalawaHonolulu Forest ReserveJoint Base Pearl Harbor-HickamMaunawiliPearl CityDiamond Head State MonumentOʻAhu Forest National Wildlife RefugeMokuleiaKaena Point State Park - Keawaula SectionMokuleia Forest ReserveEwa GentryMakua Keaau Forest ReserveNanakuliKaneoheMailiMakakiloMakaha ValleyNanakuli Forest ReserveWaiahole Forest ReserveWest Loch EstateWaianae Kai Forest ReserveKahaluuKaneohe BaseSchofield BarracksAhuimanuEast KapoleiEwa VillagesOcean PointeMakahaWaianaeWheeler AfbWahiawaWheeler Army AirfieldKo OlinaHeeiaKapoleiKalaeloaHauula Forest ReserveKaipapau Forest ReservePupukeaKawela BayPupukea-Paumalu Forest ReserveWaiahole-WaikaneKahukuWaialuaLaieHaleiwa

Nearby adventure guides

Things to Do around Maunawili

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy