Hiking Around the Island of Oahu

July 20, 2016

Guest post from our summer intern, Taylor.

What I love about Hawaii is that there’s never a shortage of things to do.

From the mountains to the ocean, Hawaii is truly a playground.

As I mentioned in my intro post, I enjoy being outdoors and active.

In this blog post, I wanted to share some of my favorite hikes around the island of Oahu.

If you’re itching to do something besides the typical tourist activities and you’re up for the challenge, take on one (or all!) of these hikes.

Ehukai Pillbox Hike – North

Up until a few summers ago, I had no idea that this hike existed – let alone that there were any hikes up North.

If you’ve heard of the Lanikai Pillboxes hike, this one is comparable in the sense that it’s fairly short/easy and leads to a pillbox with a view.

But, the one advantage of this hike is its way less crowded – I consider it a North Shore gem.

For those visiting Oahu, a trip to the North Shore is a popular attraction.

From the Sheraton Waikiki, Haleiwa is about an hour drive.

Stopping in this cute, little town is a must – wander around the shops, grab some local food, and enjoy the laidback lifestyle.


After Haleiwa, continue driving north for another 15 minutes and you’ll reach the location of the Ehukai Pillbox hike.

You can park in the Sunset Elementary School parking lot located right across of Pipeline Beach.

A sign near the front of the lot marks the entrance to the trail.

The hike is about 2 miles and only takes about 30-40 minutes to get to the top, however it can be steep and challenging at some points.

After some hiking and a few ropes to help you up, you’ll come to a midway point where there is a picnic bench – perfect for a quick breather and water break! From this point on the hike becomes more manageable and flat.

In less than 10 minutes you’ll reach the first pillbox, offering panoramic views of Oahu’s North Shore.


Pillboxes are somewhat common on Oahu hikes, as they were used as military bunkers in the past.

Now, you’ll see them covered in colorful graffiti artwork.

After cooling down and enjoying the views, hiking back down will be a breeze.

If you’re planning to head to the North Shore for the day, think about squeezing in this fairly do-able hike as it’s on the way to many beaches like Ke Ikis or Sunset Beach.

Crouching Lion Mini Hike – East


The Crouching Lion hike is probably one of my all-time favorite hikes on the island.

It’s short and offers an amazing 360 view of the island’s east side and Kahana Bay.

The catch? It’s a lengthy drive from Waikiki (about 60 min. from the Sheraton Waikiki) and is an uphill hike for a majority of the way.

However, in my opinion it’s totally worthwhile every time.

Although the journey to get to the hike is long, you’ll be treated to beautiful views and scenery as you drive alongside the ocean.

Just around the bend from the Crouching Lion Inn in Kaa’awa you can park on the side of the road and there you’ll see the opening to the hike on the mountainside across the street.

On the plus side, the hike is almost entirely shaded by trees so you don’t get as tired out from the heat.

You’ll also find a few ropes along the mountain to help you up as some sections are mostly dirt and crumbly.

Within 30-40 minutes you’ll reach the top of the mountain and have the choice of going to the left or right.

The left leads you to the top of the “lion” while the right continues onto the Pu’u Manamana trail.


Amazing view from the top of the “lion”

Of all the times I’ve hiked Crouching Lion, I was completely satisfied with just going left and doing the mini hike.

I’d recommend packing a lunch to eat at the top, as I’m certain you’ll want to spend a good chunk of time admiring the views. 

Upper Makua Cave – West

upper makua cave1

Although there aren’t as many tourist attractions on the west side, there are a few hikes (and beaches) that are worth driving out for including this one.

From our Waikiki properties, it will take you just over 1 hour to arrive in Waianae.

Pack a cooler and some snacks for the road!

Just past the popular Makua Cave on Farrington Highway, is where the trail begins.

There’s a small gravel parking area on the left side of the road that some hikers choose to park their car at.

Through the tall grass you’ll come across a clear and defined pathway up the mountain, although it is a little steep and rocky.

The hike up is fairly short, but with the incline and no shade it becomes a workout.

Follow the trail up and then you’ll come to another trail that leads towards back towards the cliff side and ocean which will bring you to the Upper Makua Cave, nestled in the mountain.

On a clear day, the view from the cave is breathtaking.

You’ll be able to see the road continuing west to Ka’ena Point, the lush mountainside, and the deep blues of the Pacific Ocean all at once. 

upper makua cave2

I did this hike with a group of friends and we spent a good 20 minutes at the cave – there isn’t much to explore inside, so we were taking pictures and soaking it all in.

Koko Head Stairs Hike – South

The first thing I must say about this hike is that I have a love/hate relationship with it.

Love it because the view can’t be beat and makes it worth the effort. Hate it because it’s like a never-ending Stairmaster with the sun beaming down on you.

This hike is the closest to Waikiki of the four, and will take you about 30 minutes to drive there.

For those who are up for a challenge, I would suggest this hike.

It’s a 1.8 mile hike on the tracks of an abandoned railway that leads up the side of Koko Head Crater – 1,106 steps to be exact.

The railway was for a tram used by the military to transport supplies to a lookout post at the summit.

My friend, Sheena, and I at the top of the stairs – we did it!

It starts off fairly flat, but as you continue to hike up the crater, it gets rapidly steeper.

On this trail, you’ll find a variety of hikers from tourists, to locals, to young children and dogs, to super fit athletes running up and back down the stairs before you even reach the halfway point.

Bring extra bottles of water and sunscreen! You may have to carry a heavier backpack, but you’ll be thankful later when it’s the middle of the afternoon and you’re exposed to the scorching sun with very little shade.

Once you reach the top, gusts of wind will hit your face and all that hard work and sweat will have paid off when you have a bird’s eye view of Hawaii Kai and the south side of the island.


The view that awaits you at the top! To the left is Hanauma Bay and to the right is Koko Marina.

What’s nice about being on an island is that no place is too far to get to.

Even if you’re staying in Waikiki, you can travel to the other side of the island in about an hour and a half.

So if you feel like venturing out and exploring other parts of the island, know that there are countless options available!


Follow #travellingwithtayhawaii on social media for all of Taylor’s adventures this summer!

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