Oahu Things to do: 5 of the Best Hikes on Oahu - Updated 2022

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The beaches on Oahu are such great place to spend some time relaxing and enjoying the salty tropical air, but when you want to get out and enjoy the lush landscape, beautiful waterfalls and spectacular views around Oahu one of the hikes on this list is just what you need.  

The following Oahu Travel Blog article, ‘Oahu Things to do: 5 of the Best Hikes on Oahu,’ features tips and information to enjoy some of the great hikes on Oahu, from short and easy hikes to longer, more challenging hikes with rewarding views of the island and the amazing Oahu coastline below.

So, kick off those flip flops, and lace up your hiking boots, grab your sunscreen, bottle of water, snacks and camera and let’s hike Oahu:

1. Diamond Head Crater
Length of Hike: 1.5 Miles
Location: Kapahulu
Level of Difficulty: Moderate

This is easily the most popular of all the Oahu hikes, simply because you can see Diamond Head from almost any spot in Waikiki including out the window of most arriving airplanes a to Oahu.

Diamond Head is an easy hike, only 45 – 70 minutes or so to complete depending on your fitness level and depending on how much time you spend taking photos and enjoying the views.

Speaking of the views, they are amazing as you reach about 750 feet above sea level at the highest point. Depending on the weather of a clear day, you can see far past Waikiki and along the coastline.

Diamond Head was originally named by early Hawaiian’s as ‘Le’ahi’ which means, ‘Tuna Ridge’, and the term Diamond Head came in 1825 when British sailors saw the Calcite Crystals sparkling in the sunlight on the sides of the crater and named the mountain ‘Diamond Hill’ which later became Diamond Head.

2. Pink Pillbox Hike
Location: Nanakui 
Length of Hike: 1.2 Miles
Level of Difficulty: Moderate

Located on the west side of Oahu, the Pink Pillbox Hike, or Pu’u O Hulu Hike, gives views of the beautiful stretches of coastline and beaches of Oahu and the surrounding homes below.  The Pink Pillbox Hike ridge splits the neighborhoods of Maili and Nanakuli. 

One of the features that makes the Pink Pillbox Hike an interesting option for hikers is that there are several route options to take you to the top of the trail to see the 5 Pillboxes.  One of the routes is longer, easier and more ‘kid friendly’ option compared to the shorter, steeper route for more fit hikers.

This is a great short hike that is close to Waikiki and rewards your efforts with great views.  If you go early in the day, the morning light is beautiful. Conversely if you choose to go later in the day you can enjoy some amazing sunsets, although you will want to be coming down the trial before you lose daylight.

3. Crouching Lion Hike
Location: Koolaulloa
Length of Hike:  .4 Miles
Level of Difficulty: Moderate

Do not let the short length of this hike fool you, the trail is short but challenging…take care. The reward for this short and steep hike is amazing views of Kahana Bay below and the cliffs of Pu’u Manamana.

As the trail begins there are no ‘warmups’ – the trail is steep from the beginning.  The vegetation will be thick and the branches from the trees are low in spots.  If the ground is wet or right after a rain, the ground can be quite slippery so be sure to take notice of your footing and wear good hiking shoes.

Crouching Lion Hike is considered by many as one of the top, if not the top hikes on Oahu as far as rewarding views goes.  Hikers will enjoy the view of the Kahana Bay below.  Depending on the time of day, the light reflecting on the water in the Bay and the ridges on the far side of the Bay make for a great photo opp.

4. Koko Head Trail
Location: Honolulu
Length of Hike: 1.8 Miles
Level of Difficulty: Hard

You will get in your cardio workout for the day after completing the Koko Head Trail!  The trail includes 1,048 stairs made up of old railroad ties/beams that lead up the side of the Koko Head Crater.  The ‘steps’ are uneven and spaced in varying distances, so each step is a bit different from the last.  

Hikers often step off the old wooden beams that are too far apart or missing altogether and use the dirt trail to either side of the railroad track.

The steepness of the trail increases as you ascend to the top of the trail. This is a very challenging hike and it will put your quads, glutes and ankles through a workout.  As challenging as this hike is there are several local hikers who will do this hike twice and sometimes 3 times in a row.

I mention this only because of how unique it was; on one visit to the top of the Koko Head Trail I saw a very it man in his early 30’s wrestling around with his two young sons who were about 4 and 5 years old. I couldn’t believe that 2 small, young boys could make their way up this trail.  But the man called his boys over to him saying it was time to go back down. The boys stood on either side of the man, who reached down, grabbed each boy by the by the top of their jeans like buckets of water and he began trotting down the trail hitting each railroad beam as the two young boys screamed with delight.  

I must have had a shocked look on my face because a nice young lady walked past me and smiled, ‘It’s my husband…he’s a S.E.A.L.  He’s showing off.’  He sure was!

The views from the top of the trail include Hanauma Bay, a bit of Waikiki and Diamond Head.

5. Seven Falls Hike
Length of Hike:  2.1 Miles
Location: Honolulu
Level of Difficulty: Moderate to Difficult

The Seven Falls Hike can be very challenging should you choose to take on the entire trail, but it is an enjoyable hike if you choose to do only the first parts, but know that you will get wet, the trail can also be quite muddy especially if after a rain.

During parts of the hike you will need to swim a bit so be sure to bring a dry bag for your phone, camera, etc.  The hike also requires a  bit of navigating over rocks, around trees and along a narrow trail at times.

At part of the Seven Falls Hike you will need to climb up waterfalls with secured ropes – a very thrilling waterfall hike to be sure.  Past the 3rd or 4th peak you should be a very fit and adventurous hiker…but the effort is worth it.

If you love to hike and if you love the payoff of a beautiful waterfall, then Oahu has many options for you to choose from.

This Oahu Travel Blog article, ‘Oahu Things to do: 5 Top Hikes on Oahu’ details just 5 of the great hikes you can enjoy during your visit to Oahu.  Look for a future Oahu Travel Blog article that will feature more Oahu Hikes!

Be sure to visit our Oahu Travel Blog and Oahu Visitors Guide for more articles on things to do, see and experience during your next visit to the island.

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