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Best Oahu Hiking Trails

Updated: Jun 12, 2023

The best Oahu hiking trails offer you scenic vistas to soak in the beauty of the island.


Check out the best Oahu hiking trails below to find easy hiking trails or trails for the more experienced hiker. The hikes are organized by region so you can make the most of your vacation.


A woman and man are at the top of a mountain taking a selfie with views of the ocean in the distance. The woman is wearing a blue hat and aviator sunglasses. The man is wearing a Hurley hat and sunglasses.
Views from Lanikai Pillbox


Best Oahu Hiking Trails in Waikiki/Honolulu


Diamond Head

Diamond Head is a crater that was formed over 300,000 years ago during a volcanic explosion. The hike is only 0.8 miles one way, but you'll gain 500 feet in elevation. The views from Diamond Head are very beautiful. Diamond Head is open 6 days a week (closed on Wednesdays) from 6am-6pm, although you can't arrive after 4pm. The hike is really popular trail as it's very close to Waikiki. You can Uber there or drive a rental vehicle. It's $10 to park if you drive and $5 per person to hike. Kids under 3 are free.


Aiea Loop Trail

Aiea Loop Trail is a beautiful hike. It's one of the few hikes that does have shade. The views from the hike are amazing. You'll get to experience walking in the trees, but you'll also have great views of the mountain ranges. The hike is 5 miles long and is a loop. The elevation gain is 1309ft but it doesn't feel that bad as you have a longer time to reach that elevation unlike some of the shorter hikes. There is parking available and the hike is free.



Best Oahu Hiking Trails on the East Side of Oahu


Koko Head Crater

Koko Head is a trail for more advanced hikers due to the trail having no shade and the need to hike uphill over 1000 stair steps. The steps are actually old railroad ties. They are not easy to climb. The trail is around 1.6 miles but remember half of that is uphill. The elevation gain is around 885ft. The views from the top are beautiful! I'd suggest going early in the morning as there's no shade and it can get very hot. There is parking available and the hike is free.


Makapu'u Lighthouse

Makapu'u Lighthouse is an easier paved trail. Like most hikes in Hawaii, there isn't shade. The hike is 2.5 miles long with an elevation gain of 505 ft. The view from the hike is very beautiful. During the winter months, you can often see whales from the hike. There is parking available and the hike is free.


Lanikai Pillbox

Lanikai Pillbox is a short hike. It's not too difficult but also isn't easy as you need to climb the ridge which can be slippery, muddy and difficult. Bring shoes with good grip. The hike is only 0.9 miles but the elevation gain is 406ft. When you get to the top you'll see the old pillbox which is a WWII bunker. You'll also be able to see Lanikai beach and the Mokulua islands. Lots of people like doing this hike early in the morning to experience the sunrise. We like to hike it and then eat breakfast at Cinnamon's afterwards. There is parking available although it can be difficult to find and the hike is free.



Best Oahu Hiking Trails on the West Side of Oahu


Ma'ili Pillbox

The Ma'ili Pillbox hike is an intermediate hike as there is no shade, and you'll have to hike uphill. The hike is only 1.6 miles with half of that being uphill, but the elevation gain is 679 feet. The views from the top are beautiful. During the winter months, this hike is a great place to spot whales. You'll also get to see the old WWII bunkers at the top. There is parking available and the hike is free.


Kaena Point

Kaena point can be accessed from the West side/Waianae or from the North Shore/Wailua. The hike is around 5 miles and is pretty flat. There is no shade and it sometimes rain due to the mountain range being right there. In the winter the hike is great for spotting whales. At the end of the hike there are tidepools where 99.9% of the time I've seen an endangered Hawaiian Monk Seal. There are only 1000+ left in Hawaii. Bring lots of water for this hike. There is parking available and the hike is free.


Best Oahu Hiking Trails on the North Shore


Kaena Point

Kaena point can be accessed from the West side/Waianae or from the North Shore/Wailua. The hike is around 5 miles and is pretty flat. There is no shade and it sometimes rain due to the mountain range being right there. In the winter the hike is great for spotting whales. At the end of the hike there are tide pools where 99.9% of the time I've seen an endangered Hawaiian Monk Seal. There are only 1000+ left in Hawaii. Bring lots of water for this hike. There is parking available and the hike is free.

A woman is standing at the top of a mountain with views of the ocean behind her. The ocean is bright blue. She is wearing black shorts and shirt and a blue hat.
Lanikai Pillbox

Safety Tips---Remember to…

  • bring lots of water

  • start your hike early (many hikes are not shaded)

  • bring good shoes (rain may occur and the trails can become slippery)

  • never leave anything valuable in your vehicle.

Unfortunately, break-ins occur regularly at the best Oahu hiking trails. If you must leave things in your vehicle, put them in your trunk and do this before you get to your final destination as people will watch you and see you put stuff in your trunk at the trailhead. I lived there and never had my vehicle broken into, but I also never left a thing in my car. We also left our car unlocked to avoid a broken window. With a few safety steps, you'll enjoy the beauty of an island hike. Hope to see you on the trails!


If you've been dreaming of a Hawaiian vacation, but don't know where to start to plan your vacation, book your zoom consultation with The Gypsea Traveller to learn more. Libbi can help you book a vacation package that includes your flight, the perfect resort for you, car rental or airport transfers and insurance. She can also custom design an itinerary for you based on excursion and restaurant recommendations.


Libbi lives in Hawaii and has visited all of the Hawaiian Islands. She loves helping clients book their dream vacation to the Hawaiian Islands. You can visit www.thegypseatraveller.com and click on "Schedule Consult" to choose a date/time to zoom with Libbi, The Gypsea Traveller


A white banner with turqoise stripes that lists Libbi, The Gypsea Traveller contact information. There is also a picture of Libbi at a beach in Hawaii with a colorful dress on and a yellow flower behind her ear.

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