I’ll bet you’re in Hawaii for the beaches, the poke bowls, and the sunsets that melt your stress into the Pacific. But somewhere between your third shave ice and that same beachside view along the shore, you’ll start craving an even better view.
Your next thought? Go on a hike!
Here’s the good news: You don’t need to be a hardcore hiker (or own a single piece of “hiking gear”) to score Oahu’s most iconic panoramas. I’ve trekked many trails on this island—sometimes in sneakers, once in sandals (do not recommend unless you like the dusty toes look)—so I have a good idea of which paths deliver the biggest bang for your buck.
These are the hikes for people who want adventure without the asterisks. No 4 a.m. alarms, no calf-burning marathons, and definitely no $200 hiking boots. Just straightforward trails where “easy” doesn’t mean “boring,” and “short” doesn’t mean “meh.”
Below is a quick list of the best hikes in Oahu, suitable for every type of traveler, from novice hikers to extreme adventurers, so you have no excuse to not get out there!
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Table of Contents
DIAMOND HEAD TRAIL
Honolulu
This hike is for you if: You’re looking for a quick and relatively easy hike to see a panoramic view of the island; you have no car to get to any other hike on the island.
- 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.
Let’s talk about Oahu’s iconic hike: Diamond Head. Yes, that volcanic crater you’ve seen plastered on every Hawaii postcard. The view from the top? Undeniably epic—a 360° punch of turquoise ocean, Waikiki’s skyline, and lush ridges that’ll make your friends back home jealous.
I’ll be honest though, it took me quite a few trips to Hawaii before actually doing this hike for myself. Why? Between the parking fee and the per-person entry charge (since when do we pay admission for Mother Nature?!), I avoided it for years. Yes, the views are great, but I’m not a fan of paying to hike.
These days, the government’s cracked down with a reservation system just to park. Yep, you read that right—you need a slot to access the trailhead. Check their website for updates, because rules here change from time to time.
That said, Diamond Head is still the MVP for a reason. It’s short (2 miles round-trip), steep but manageable (you’ll feel the burn, but even the most gym-averse travelers should be able to do it). It’s also great for tourists staying in Waikiki without access to a car.
Want to avoid the headache of finding parking and all that mumbo jumbo? There are various guided excursions and self-guided ones that handle all the Diamond Head hike logistics for you, including admission fees, round-trip transportation from your hotel, water, and maps.
Along the way, you’ll dodge tour groups, sweat through your tank top, and fight for a spot at the lookout without strangers photobombing you in the background. But when you finally lock eyes with that coastline, it’ll be pretty dang sweet.
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 $10 per vehicle AND $5 per walk-in visitor.
LANIKAI PILLBOX HIKE
East Shore
This hike is for you if: you are an early riser who 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
- AllTrails: Kaiwa Ridge Trail (Lanikai Pillbox)
The Lanikai Pillbox Hike is also known as the Kaiwa Ridge Trail. The hike itself is quite steep but very short, which means it’s great for people who have other plans for the day and want to fit in a hike with a quick payoff.
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 rises over the horizon.
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 for hikers, but this is a popular trail, so get here early or later in the day.
KOKO HEAD HIKE
South Shore
This hike is for you if: You are a fit person 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. We like the sunrises here.
- AllTrails: Koko Head Trail
A popular one for the athletic crowd, this hike features over 1,000 “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.
Be aware that there are two small sections where the railroad slats don’t have solid ground underneath them, which can be terrifying if you’re not comfortable walking across gaps with no solid ground beneath you. In the two spots where this happens, there are alternate paths you can take to avoid the exposed slats.
I can get up Koko Head pretty quickly (for reference, it takes me 20-23 minutes to ascend without stopping), and my next goal is to complete it twice in one day. Sunrise is also my favorite time to hike it because it gets way too hot during the day for all these stairs!
👉 Pro Tip: Come dressed appropriately. This is not a walk in the park kind of hike. On our last Koko Head hike, we saw a couple who had Starbucks cups in hand. The girl was also wearing jean shorts. They clearly did not know about the physical demands of Koko Head!
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!
‘EHUKAI PILLBOX HIKE
North Shore
This hike is for you if: you’re looking for a quick hike during your North Shore day trip.
- Difficulty: Moderate
- Length: 45 minutes to 1 hour roundtrip
- Best time to hike: Any time of the day (it’s surprisingly shaded along the way), or during sunset.
- AllTrails: ʻEhukai Pillbox Trail
The ʻEhukai Pillbox Trail is a short but steep 1.4-mile (2.3 km) round-trip hike on Oʻahu’s North Shore, leading to two WWII-era bunkers with sweeping coastline views. The trail starts with a flat section before climbing 300 feet (91 m) up a steep hill, which can be muddy after rain.
If it does happen to be muddy, you can use the ropes to guide your way up. They’re only available at the steep parts of the hike.
At 0.6 miles (1.0 km), you’ll reach the first (Upper) pillbox, but many hikers prefer continuing to the second (Lower) pillbox for even better views. From here, you’ll get a panoramic look at Pūpūkea, the North Shore, and Kaʻena Point to the west. If the waves are high, you’ll have a prime vantage point to watch world-class surfers at Banzai Pipeline.
I definitely recommend you walk through the tunnel into the pillbox itself rather than just looking out at the top. You get super cool bunker views in there!
This is one of the best effort-to-reward sunset hikes on the island. Trekking poles may help on the descent, and as always, bring water and prepare for muddy conditions if it has rained.
How To Get There:
Address: 59-178 Kamehameha Hwy. Haleiwa, HI 96712
Parking available at Sunset Beach Neighborhood Park or ʻEhukai Beach Park (avoid the school lot).
OLOMANA RIDGE TRAIL
East Shore
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
- AllTrails: Mt. Olomana Trail (Three Peaks)
Also known as the Three Peaks Trail, this is one of the more dangerous hikes on the island. The first peak is relatively straightforward despite being a steep incline. Once you pass this first peak, 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 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:
Address: 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.
MOANALUA VALLEY TRAIL (HAIKU STAIRS, THE LEGAL WAY)
Honolulu
This hike is for you if: you’re relatively fit, want to experience something similar to Haiku Stairs, and are 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
- AllTrails: Moanalua Valley and Tripler Ridge Trail Loop
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.
If you want reviews of the most recent trail conditions, check out AllTrails.
How to get there:
Address: Moanalua Valley Trail Start (Kulana’ahane) 1849 Ala Aolani St, Honolulu, HI 96819.
There is free parking at 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.
Planning your trip to Oahu? Here are a few other guides that may be of use to you:
- Oahu For First Timers: 35+ Things You Need To Know
- 15 Can’t-Miss Activities At The Polynesian Cultural Center
- The Ultimate Oahu 4-Day Itinerary For Budget Travelers
- 125 Bucket List Things To Do In Oahu, Hawaii
- The North Shore: 15 Stops For A Perfect Day Trip
- 33 Fun + Totally Free Family Activities On Oahu
- Hawaii Outfit Ideas: Beaches, Luaus, and Beyond
