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United States
Honolulu County

Maili

The best walks and hikes around Maili

4.6

(30)

741

hikers

7

hikes

Hiking around Maili, located on the leeward side of Oahu, Hawaii, offers diverse landscapes for outdoor enthusiasts. The region is characterized by its rugged Waianae Mountains meeting the Pacific Ocean, providing both coastal and mountain vistas. Trails often feature varied terrain, from hard-packed dirt paths to rocky sections, showcasing the natural beauty of the island's western coast.

Best hiking trails around Maili

  • The most popular hiking route is Pink Pillbox Hike/Puʻu O Hulu Trail to PuʻUʻOhulu Kai — Oʻahu,…

Last updated: May 28, 2026

4.8

(12)

233

hikers

#1.

Pink Pillbox Hike/Puʻu O Hulu Trail to PuʻUʻOhulu Kai — Oʻahu

2.22km

00:53

170m

170m

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

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Easy

4.6

(8)

69

hikers

10.9km

05:57

1,040m

1,040m

Hard hike. Very good fitness required. Sure-footedness, sturdy shoes and alpine experience required.

Hard
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9

hikers

4.40km

02:00

320m

320m

Hard hike. Good fitness required. Sure-footedness, sturdy shoes and alpine experience required.

Hard

4.9

(9)

175

hikers

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
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Popular around Maili

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Tips from the Community

Christopher
October 18, 2023, PuʻUʻOhulu Kai

This secondpillbox is an old WWII observatory point that feels like it's on the edge of the world. Being that this point is on the west coast, the sunsets are absolutely ludicrusly amazing!

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Once you reach the summit with its helipad, it's finally time to have a break and appreciate what you have achieved. Enjoy the picturesque views of the surrounding landscape.

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At the top of this trail is a pink pillbox that provides scenic views in real life, and some instagram worthy content. The pillbox provides some of the best views on this side of the island and being that it is west facing, is ideal at sunset.

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Puʻu Hapapa Summit Trail is the challenging part of your hike to Puʻu Hapapa Summit. It includes many tough inclines, rock scrambling and drop-offs that are not for you if you are afraid of heights. But on the other hand, this trail also offers great views, especially once you reach the ridge.

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Kolekole Trail is the first section of the hike to Puʻu Hapapa. It's a relatively easy hike without big inclines, and you don't need to have any experience in hiking (if you however want to continue to the summit, we're talking about much more inclines and more demanding trails!). As the trail is located on military land, make sure that you need a valid DOD card or a visitor pass to access the trail.

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Before attempting to hike along Mount Kaʻala Trail, please be aware that this might be one of the toughest hikes on the island. The hike includes almost 3,600 feet in altitude and there are many sections where you have to scramble over muddy boulders with the help of attached ropes (gloves might be useful). But if you're up for the challenge, you will love the views along your way, so get ready for a great adventure!

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With an elevation of 4,026 feet, Mount Kaʻala is the highest point on Oʻahu. As you might imagine, that means spectacular views to the north-shore and even to the city of Honolulu. Give yourself a break and enjoy the beauty of this place.

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Puʻu O Hulu Trail is known by many people under its unofficial name 'Pink Pillbox Hike'. The last section of the trail, leading up the mountain of PuʻUʻOhulu Kai, includes multiple pillboxes (old military bunkers). One of them is painted pink to raise awareness for breast cancer and became the unofficial namesake of the trail.

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Frequently Asked Questions

What kind of terrain can I expect on hiking trails in Maili?

Hiking trails in Maili offer a diverse range of terrain. You'll find everything from hard-packed dirt paths and switchbacks, particularly on ascents like the Pink Pillbox Hike, to rocky sections and even sand dunes along coastal routes such as the Ka'ena Point Trail. This variety provides different challenges and scenic experiences.

Are there any easy hiking trails suitable for beginners in Maili?

Yes, Maili offers several easy hiking options. For instance, the Pink Pillbox Hike/Puʻu O Hulu Trail is considered easy, taking about 53 minutes to complete. Other easy routes include the View of Ko Olina Lagoon – Koi Pond loop from Kīpuka Lawn and the View of Ko Olina Lagoon loop from Laniwai – A Disney Spa, both offering pleasant, less strenuous walks.

What are some notable landmarks or viewpoints I can see while hiking in Maili?

Maili's trails are rich with landmarks and stunning viewpoints. The Pink Pillbox Hike leads to historical military pillboxes and offers incredible views of the Waianae coast and the PuʻUʻOhulu Kai summit. For panoramic island views, the challenging Mount Ka'ala Trail ascends to Oahu's highest peak. You can also visit the historical site of Kaneaki Heiau nearby.

Are there any challenging hikes in Maili for experienced hikers?

Yes, for experienced hikers seeking a challenge, Maili offers difficult trails. The Mount Ka'ala Trail is a difficult 6.8-mile path leading to Oahu's highest peak, providing extensive panoramic views. Another challenging option is the Pu'u Hapapa Summit Trail, a 2.7-mile route through mountainous terrain.

What do other hikers say about the trails in Maili?

The hiking routes in Maili are highly regarded by the komoot community, holding an average score of 4.5 stars from over 19 reviews. Hikers often praise the adventurous ascents, the rewarding coastal and mountain vistas, and the unique historical elements like the military pillboxes.

Can I find coastal walks or trails with ocean views in Maili?

Absolutely. Maili is known for its stunning coastal and mountain views. Trails like the Ka'ena Point Trail, located near Maili, offer spectacular ocean vistas as you traverse sand dunes and jagged reefs. Many routes provide glimpses of the rugged beauty where the Waianae Mountains meet the Pacific Ocean.

Are there any historical sites or unique features to explore on Maili's trails?

Yes, Maili's trails offer unique historical and natural features. The Pink Pillbox Hike is famous for its military pillboxes, adding a historical element to the trek. You can also find the ancient Hawaiian temple of Kaneaki Heiau nearby, offering insight into the region's cultural past.

What kind of wildlife or flora can I expect to see while hiking in Maili?

The Maili area is home to diverse flora and fauna. The Maili Pillbox Hike, for example, is known for various bird species, giving it a feel akin to a bird sanctuary. While hiking, you might encounter native Hawaiian plants and potentially cultural significant flora like the Maile vine, which was historically found in the island's native forests.

How many hiking routes are available in the Maili area?

There are approximately 6 hiking routes available in the Maili area, catering to various skill levels. These include easy loops and more challenging summit trails, ensuring there's something for everyone.

What are the typical durations for hikes in Maili?

Hike durations in Maili vary significantly depending on the trail's difficulty and length. Easy routes like the Pink Pillbox Hike can be completed in under an hour, while more difficult trails such as the Mount Ka'ala Trail can take nearly six hours to complete.

Are there any family-friendly hiking options in Maili?

While specific family-friendly designations are not always explicit, the easier routes in Maili are generally suitable for families. The View of Ko Olina Lagoon loop from Laniwai – A Disney Spa, for instance, is a shorter, easy walk that could be enjoyable for families.

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