6 Best Hikes In Oahu For Every Type of Traveler

The natural beauty of the Hawaiian Islands is undeniable. Oahu has it all– good food, kind people, and amazing hikes. All over the island you can find beautiful vistas, gushing waterfalls, and steep ridgelines boasting the most phenomenal views. If you’re planning a trip to Oahu, you definitely need to squeeze in a hike. I’ve compiled a list of the best hikes in Oahu, suitable for every type of person, from novice hikers to extreme adventurers, so you have no excuse to not get out there!

Best Hikes On Oahu - www.travelswithelle.com



This hike is for you if: You’re looking for a quick hike to see a panoramic view of the island; you have no car
Difficulty: Easy to Moderate
Length: 1.5 to 2 hours roundtrip
Best time to hike: Anytime – The trail is open 6am until 6pm, although last entry is 4.30pm.

Diamond Head Hike - www.travelswithelle.com

Diamond Head Hike - www.travelswithelle.com

This trail is named after Oahu’s most widely known landmark, Diamond Head, a massive chunk of volcanic rock situated on the Southwestern coast of the island. This is the most touristy hike as it is very close to Waikiki, but has a great view. It’s is also simple enough for most people of all ages with minimal hiking experience to enjoy. The climb up to the top is roughly two miles, yet there is a lot of incline. Once you are at the top, however, you’ll realize your efforts have paid off as you come face to face with one of the most spectacular views of the Hawaiian coast.

How to get there:

The trailhead is adjacent to the parking lot within Diamond Head State Monument. The entrance is off Diamond Head Road between Makapu’u Avenue and 18th Avenue, Honolulu. Entry fee of $5 per vehicle or $1 per walk-in visitor.


This hike is for you if: you are an early riser that wants to experience an epic sunrise; you are short on time but still want to hike.
Difficulty: Easy to Moderate, but short
Length: 1 hour roundtrip to the first pillbox, 3 hours roundtrip for all 3 pillboxes
Best time to hike: Anytime, but some people come for the sunrise specifically

Oahu, Hawaii - www.travelswithelle.com

Lanikai Pillbox Hike - www.travelswithelle.com

Also known as The Kaiwa Ridge Trail. The hike itself is quite steep but very short. I was able to complete the hike to the first pillbox effortlessly in sports sandals, but I would recommend actual shoes. You can continue on to reach the other 2 pillboxes if you want to extend the hike. There is no defined trail but because it is so popular, there is an unofficial trail that is very easy to follow. When in doubt, just follow all the people in workout clothes.

This hike is highly recommended for sunrises. Since it’s pretty short, you won’t need to wake up too many hours before the sunrise. To catch the sunrise from start to finish it would be best to begin hiking 30-40 minutes before the sun emerges.

How to get there:

Easy to find. It is directly across from the Mid-Pacific Country Club parking lot. Unlike many hikes on the island, there is signage. Look out for the “Lanikai Pillbox Hike” sign. There is ample parking in the neighborhood hikers, but this is a popular trail so get here early or later in the day.

Read More: The Packing List for Hawaii and Other Tropical Beach Destinations


This hike is for you if: You are a fitness enthusiast looking to get in a good sweat and a good leg burn
Difficulty: Strenuous
Length: 45 minutes to 2 hours roundtrip
Best time to hike: As early as possible since it gets so hot

Oahu, Hawaii - www.travelswithelle.com
Oahu, Hawaii - www.travelswithelle.com

36 Hours On Oahu, Hawaii - www.travelswithelle.com

A popular one for the athletic crowd, this hike features over 1000 “stairs” up to the top where you’ll be greeted with incredible 360 degree views. It can take anywhere from 15 minutes to an hour to reach the top, depending on your pace. Make sure to bring lots of water because you will be sweating a lot. This is a great workout that will make your legs feel like jello and get you drenched in your own sweat— but hey, you can enjoy that plate lunch or Dole whip later on guilt-free. I can get up Koko Head pretty quickly, and my next goal is to complete it twice in one day.

How to get there:

After parking in the Koko Head District Park parking lot, you will find an easily identifiable trail a bit past the lot that leads to the start of the climb up the mountainside. If you’re lost, ask others around you or follow everyone else!

36 Hours On Oahu, Hawaii - www.travelswithelle.com


This hike is for you if: you’re adventurous, not afraid of heights, and looking for a real challenge
Difficulty: Strenuous
Length: 1.5 hours to get to first peak; 6 miles total, allocate up to half a day for this depending on how far you go
Best time to hike: recommended to go during dry conditions

Also known as Three Peaks Trail, this is one of the more dangerous hikes on the island. The first peak is relatively straight-forward despite being a steep incline. Once you pass this guy, the real challenge begins. I’ve heard of a lot of people turning back after either the first peak or second peak because things get a bit sketchier after this, depending on your level of confidence and sure-footedness. The first peak is known to have the best views, anyway. On a drier day you should be fine, just bring sturdy shoes with traction. I would probably not attempt this on a windy or rainy day. Once you become comfortable with what you’ve gotten yourself into, you can really enjoy this breathtaking trail.

How to get there:

770 Auloa Road, Kailua
Park in the Maunawili neighborhood just outside the golf course entrance on Auloa Road. There’s usually street parking near the intersection. Watch out for tow-away zones, and be respectful of the neighborhood. Once you’ve parked, walk down the road through Luana Hills until it turns into the Royal Hawaiian Golf Club. Pass the guard shack and, after about half a mile, you’ll see the white sign for Olomana Trail on the left.

Read More: Oahu Hawaii: Top Tips For First Timers


This hike is for you if: you’re adventurous, not afraid of heights or of potentially getting fined by the police, and looking for a real challenge
Difficulty: Strenuous
Length: 4-6 hours
Best time to hike: Start before sunrise to catch it, or when the security guard is not there.

Oahu, Hawaii - www.travelswithelle.com

Oahu, Hawaii - www.travelswithelle.comThe infamous Haiku Stairs. Popularly known as the Stairway to Heaven, this illegal hike consisted of 3,922 stairs leading up the imposing mountain ridge, often at a vertical incline, with only a hand-rail to catch you from slipping. This is possibly one of the most famous and/or best hikes in Hawaii. As stated previously, this hike is actually illegal—the path was shut down after some damage occurred in 2015. Hikers to this day still attempt it (some successfully completing it unscathed, some getting fined by police if the security guard onsite isn’t bluffing about calling them).

How to get there:

Park around 46-24 Kuneki Pl, Kaneohe, HI 96744, a residential neighborhood with ample parking. Walk towards the entrance, near 46-490 Kuneki St, where you’ll see a gate. Get to the other side— crawl under, climb, whatever.

It’s a lot of work to explain how to get to the trailhead, plus the method of getting to the trailhead is always changing so I’d recommend going on All Trails or Yelp and reading other people’s most recent accounts on how they’re getting in these days. By doing this, you will also get insight on the latest trail and weather conditions, how much fines are costing people, and latest tips on how to bypass the security guard.

Oahu, Hawaii - www.travelswithelle.com

Oahu, Hawaii - www.travelswithelle.com
Alternative: There is a back way up the Stairway to Heaven. This route is much longer, but it’s legal and you get to reach the viewpoint of the Haiku Stairs without fearing for your life or wallet. You don’t actually use the stairs to reach the viewpoint but you can still make contact with the stairs for some photos before returning down the legal route. (Note: Being on the stairs is still considered illegal, so that part is up to you.) If you want to experience a portion of the Haiku Stairs but also rest easy and avoid any chance of a being fined by the police, try this route. See details below.


This hike is for you if: you’rerelatively fit, want to experience something similar to Haiku Stairs, and looking for a day-long adventure
Difficulty: Strenuous
Length: 5-7 hours roundtrip (9.2 miles total)
Best time to hike: Moanalua Valley Trail is open 7am – 7pm, recommended to go during dry conditions

Oahu, Hawaii - www.travelswithelle.com
The only way to legally hike to the Haiku Stairs (Stairway to Heaven) starts at the Moanalua Valley Trail. Though it is by far the easiest way up, it still has some sections of nearly vertical, rope and muddy sections. Try to go during drier conditions, as this is a steep and sometimes very muddy hike that has led to injuries. This is an out-and-back trail.

The Outbound Collective has a good tutorial on how to hike this— check it out here. If you want reviews of most recent trail conditions, check out All Trails.

How to get there:

Address: Moanalua Valley Trail Start (Kulana’ahane) 1849 Ala Aolani St, Honolulu, HI 96819.

There is free parking a the start of the trailhead, toilets and a water fountain.
You’ll see a trail leading up into the bushes. Follow that and you will come to a green metal barricade-looking gate. Go through this and continue down the wide trail to begin.

And there you have it, our list of the top hikes in Oahu, Hawaii! Hopefully at least one of them piqued your interest because there’s so much natural beauty in Hawaii that should not be missed. Safe and happy travels in Hawaii!

Read More: 

The Packing List for Hawaii and Other Tropical Beach Destinations

Oahu Hawaii: Top Tips For First Timers

36 Hours In Oahu, Hawaii

In Photos: Oahu, Hawaii


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Elle Leung

My name is Elle and I'm a travel blogger and adventurer based in California. I love helping people plan trips and create unique itineraries based on their interests and their budgets. I'm a huge fan of outdoor adventures and doing off-the-beaten-path things in my state (and all around the world too)!

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