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7 Best Hikes in Oahu, Hawaii

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7 Best Hikes in Oahu, Hawaii

Planning out all the best hikes to go on while you’re exploring the beautiful island of Oahu?

Hawaii was the first tropical destination Adam and I ever visited together, and it totally made us fall in love.

From the palm trees lining the shores of the clear blue ocean to the vibrant and exciting food scene, there’s just so much to love about Hawaii.

We managed to get in quite a bit of hiking during our trip to Oahu, and I’ll be sharing some of the best ones we went on (or wished we went on!)

Here are the best hikes to go on in Oahu, ranked from the easiest to the most difficult!

The best hikes on Oahu

Mauniwili Falls

Mauniwili Falls isn’t the craziest waterfall we’ve ever seen, but it’s still a nice hike that’s very family-friendly.

Being beneath the trees makes it a lot cooler even if it’s still hot out.

The beginning of the trail is the most beautiful in my opinion, and it really makes you feel like you’re standing in the middle of a fairytale paradise.

Don’t go in the water once you get to the end – apparently there’s a disease in there that gives you similar symptoms to the flu.

We cringed hard when we saw a dude fully jump in and rub the water all over his face. *vomits*

LOCATION: 965P+JH Maunawili, HI

The Mauniwili Falls hike is one of the best hikes to add to your Oahu itinerary
Mauniwili Falls in Oahu, Hawaii
Somewhere along the Mauniwili Falls trail.

Makapu’u Lighthouse Trail

While the Makapu’u Lighthouse Trail is completely paved, it’s actually a bit difficult because it’s an uphill walk the whole way through.

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There were quite a few families and people with strollers on the trail, so it’s totally doable if you’re visiting with family or kids!

You can’t go inside the actual Makapu’u Lighthouse, but even just looking at it from afar along the trail is cool.

You can hike up past the trail to a pillbox and even higher views, but I’d recommend hiking shoes for this (like the Columbia Newton Hiking Boots) because it’s a little difficult in just sneakers.

LOCATION: Makapuu Lighthouse Rd, Honolulu, HI

Makapu'u Lighthouse Trail in Oahu, Hawaii
A view of the Makapu’u Lighthouse.
Makapu'u Lighthouse Trail in Oahu, Hawaii
The Makapu'u Lighthouse Trail hike is one of the best hikes to add to your Oahu itinerary
Makapu'u Lighthouse Trail in Oahu, Hawaii
Just look at that view!

Diamond Head Crater

Diamond Head Crater is probably my favourite hike in all of Oahu.

It was fun, challenging, and the view at the top was fantastic!

We went a bit later in the morning, and it was pretty packed, but not completely unbearable.

There were a lot of families and older people on the trail, but we were able to pass them easily.

There’s a pillbox people hike to at the end of the trail, but do it at your own risk – it’s a bit dangerous to get to!

LOCATION: Kapahulu, Honolulu, HI

Diamond Head Crater Hike in Oahu, Hawaii
A view of the pillbox from the end of the Diamond Head Crater trail.
Diamond Head Crater Hike in Oahu, Hawaii
Diamond Head Crater Hike in Oahu, Hawaii
Inside the pillbox.
The Diamond Head Crater hike is one of the best hikes to add to your Oahu itinerary

Pillbox Hike

The Pillbox Hike was actually the first hike we did while in Oahu, and phew, it was a tough one.

We weren’t prepared for how unbelievably hot it would be hiking underneath the Hawaiian sun, and I didn’t wear proper hiking shoes!

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The uphill walk is pretty tough and the sandy trail makes it a bit difficult to get back down, but the stunning views at the top of the trail are totally worth it.

Just be prepared with proper hiking shoes and plenty of water when you go on the Pillbox Hike!

LOCATION: 265 Kaelepulu Dr, Kailua, HI

The Pillbox Hikes is one of the best hikes to add to your Oahu itinerary
Pillbox Hike in Oahu, Hawaii
Pillbox Hike in Oahu, Hawaii

Koko Head Crater

We really wanted to hike Koko Head Crater while we were in Oahu, but we didn’t manage to fit it into our schedule.

We were also just exhausted from all the hiking we did on the other trails, on top of all the other activities we had planned!

Koko Head is known as one of the best hikes on Oahu, and we’ll definitely hike it ourselves someday.

The trail goes along an abandoned railroad track, which is pretty cool.

It’s also known to be a stair master workout, so do plenty of stretching and get ready for an uphill battle!

LOCATION: 7604 Koko Head Park Rd #7602, Honolulu, HI | Website

Maili Pillbox

I was most excited to hike the Maili Pillbox trail (also known as the Pink Pillbox hike), and it turned out to be the toughest one.

It’s not an official trail, and you’re pretty much climbing up a sandy hill in direct sunlight for 30 minutes one way.

We had just come from a filling brunch where we shared a pitcher of mimosas, which probably wasn’t the best idea.

Do bring plenty of water while you’re here – we took tons of water breaks along the way!

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Maili Pillbox hike in Oahu, Hawaii
We made it to the top of the trail!
Maili Pillbox hike in Oahu, Hawaii
The pink pillbox!
The Maili Pillbox hike is one of the best hikes to add to your Oahu itinerary
Maili Pillbox hike in Oahu, Hawaii

Stairway to Heaven

Okay, so the main trail leading up to the Stairway to Heaven is actually illegal, and the police can fine you up to $1000 if they catch you there.

It was built during WWII for soldiers to access the radio antenna at the top, and since it’s abandoned, the stairs are rickety and not maintained at all.

There is however a legal route from the opposite side, but it’s an 8 hour roundtrip hike.

We weren’t fit enough to do the Stairway to Heaven hike this time around, but we’ll hopefully do it someday!

You can find full on YouTube videos showing you how to take the legal route if you’re interested.

Travel blogger Journey Era also has a blog post all about both the illegal and legal routes to the Stairway to Heaven (also known as the Haiku Stairs).

LOCATION: Moanalua Valley Trail, HI

Hawaii flights & accommodations

Looking to book your flights and accommodations for Hawaii?

I love booking all of my flights and hotels on Expedia and collecting points towards free rewards.

As most hotels were out of our budget, we opted for an Airbnb (and even got a weekly discount on it).

We stayed at an Airbnb near Waikiki Beach, and it was the perfect location.

Waikiki is the main touristy part of Oahu, and you could really spend all your time here if you wanted to.

There are tons of amazing restaurants, great shopping, and fun beach activities all within walking distance!

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The great thing about Oahu is that you can basically drive from one end of the island to the other in an hour (without traffic).

We usually stay in multiple accommodations in areas we’ll be visiting, but we were able to stay in one place the entire time!

I also have a separate blog post all about how to find the best Airbnbs.

If you’re willing to spend a bit on accommodations, the Royal Hawaiian and Moana Surfrider are both gorgeous hotels right on Waikiki Beach.

The Hilton Hawaiian Village has a great outdoor shopping centre within it, and they have free fireworks every Friday evening (open to the public).

Best hikes on Oahu:

  1. Mauniwili Falls
  2. Makapu’u Lighthouse Trail
  3. Diamond Head Crater
  4. Koko Head Crater
  5. Pillbox Hike
  6. Maili Pillbox Hike
  7. Stairway to Heaven

Hawaii has some of the best hiking trails in the world, and we can’t wait to check out the hikes on the other islands.

We had so much fun doing hikes on Oahu during our trip!

You can check out my Oahu vlog on YouTube to see more of our trip.

If you’re looking for things to do in Honolulu, check out these tours!

Have you been on any of these Oahu hikes? What are some of the best hikes in Hawaii in your opinion? Let me know on Twitter or Instagram!

If you’re planning a trip to Hawaii, here are some other posts to help you plan your perfect trip:

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Be sure to keep up with me on InstagramTwitter, Facebook, and Pinterest if you aren’t already!

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Jessica Lam | Toronto lifestyle, fashion, beauty, and travel blogger | Diary of a Toronto Girl, a Canadian lifestyle blog

Best hikes on Oahu
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