Your first Oahu hike

So, you finally made to Hawaii. Magic. And you want to go hiking on Oahu. There’s a surprising number of options. As someone who’s been hiking the island for decades, here’s my guide to deciding on your first hike, whether you are a beginner or a seasoned mountain climber. It (somewhat) assumes you are a tourist or visitor, and you’re staying in Honolulu. And I’ve left out a lot of details, you can Google the details of any of these trails for directions and the like.

Easy/Kids: Lanikai Pillbox Trail, Diamond Head, or Makapu’u Lighthouse.
Intermediate: Lulumahu Falls, Aiea Loop Trail, or 
Advanced: Kuli’ou’ou or Olomana.

Easy Trails

Are you a relative beginner as a hiker? Want some great views without too much work?

  1. Get yourself to the Lanikai Pillbox Trail. A short, 30 minute climb to some WWII pillboxes, concrete bunkers used for lookouts.

If you’re not staying on the windward side (few do), then make a day of it, combine it with a trip to Kailua Beach and a meal in downtown Kailua.

Pros: Short (30 min), Views (out of this world), Safe (wear real shoes though, don’t hike in your flip-flops (or “slippas”, as the locals would say — a friend broke an ankle as the trail is very eroded in spots). 
Cons: You will be on this trail with a hundred new friends. Seriously. About 1000 people a day hit this. Don’t go on a weekend.

2. Hit Diamond Head. Another short (but steep) climb. Much of the “trail” is really concrete stairs leading to the lookout. But the views of downtown Honolulu are hard to beat.

Pros: Easy access from Honolulu, Awesome views. Doesn’t take long.
Cons: Crowded. Lots of concrete and stairs.

3. Makapuu Lighthouse trail

The Makapu’u area is awesome. Makapu’u beach is one of our favorite beaches on the island. Mostly a locals beach, great waves for bodysurfing, and not too crowded. The Lighthouse hike is an easy stroll with amazing views. It’s easily accessible from Honolulu (30 minutes from downtown), or from the Windward side. The trail is mostly paved, and you’ll get a amazing views of the famous Lighthouse as well as the entire windward shore. Do yourself a favor and combine this with a stop at Makapu’u beach and lunch at Keneke’s, a local plate lunch shop.

Pros: Quick & easy, awesome views, only “moderately” crowded.
Cons: Mostly paved. Somewhat crowded.


  1. Lulumahu Falls

Lulumahu falls are also easily accessed from both downtown Honolulu and and the Windward side.

Head up the Pali Highway, near the top you will see a bunch of cars parked in a dirt area, right where Nuuanu Pali Drive runs into the Pali Highway. There’s an entrance there to the trail. Just follow the people :). The trail to the falls will take you maybe 45 minutes (assuming no wrong turns — the trail is not extremely well marked). The trail is ok for smaller kids who like to hike. If you have a bit of extra time the bamboo forest and the ruins of Kamehameha III make for an Indiana Jones style experience.

Pros: Indiana Jones. Waterfalls. Nuff Said.

Cons: Can be crowded. Not hard to get off the trail. Not a sanctioned state trail, but tons of people on it.

2. Aiea Loop Trail.

Pros: An ancient Hawaiian heiau (religious temple built from rocks). Gorgeous hawaiian Ohia flowers. A commanding view of the H3 highway and Halawa valley. A lost WWII bomber (I’ve not found it — yet — but it’s there). Relatively flat, 5m round trip hike.
Cons: It’s not much of a workout, pretty flat. But fun


  1. Kuli’ou-’ou Ridge Trail

This trail is a workout. You start in a Honolulu neighborhood and end at the top of the Koolau mountain range, looking down into Waimanalo, with commanding views in all directions. Along the way you’ll go through a number of different “zones” of differing vegetation.

Pros: Great workout, amazing views, high quality trail.
Cons: A stairmaster section at the end. But it’s worth it.

2. Olomana

Probably the best known Windward side hike. It’s not for the faint hearted. You’ll climb 1600 feet up a knife edge ridge, climbing with the assistance of ropes for 10–15' in a few places. There are three peaks. The first is a workout but doable. The 2nd peak is not too much further, but you don’t get that much extra out of it, so I’d skip it. Don’t go to the 3rd peak. People die there. About once a year. Including experienced hikers. Just don’t.

Pros: Great workout, Amazing views, easily accessible.
Cons: Ropes. Mild danger. Extreme danger on 3rd peak. Just don’t.


  1. You will have heard of Stairway to Heaven, aka Haiku Stairs. I don’t advise it. The stairs have been heavily damaged by recent storms, and you’ll expose yourself to tresspassing charges and a fine. Not fun.
  2. The definitive guide to Oahu hiking is David Ball’s book, highly recommended.

3. If you are a deeply experienced hiker and into extreme hiking, check out this site for (dangerous) adventures. (what I call “advanced” here, they call “easy” or “intermediate”. You have been warned.)