Oahu has plenty of famous, jaw dropping hikes. While Kauai usually gets the buzz for being the hiker’s paradise, most of those epic drone shots you see plastered on social media by YouTubers and influencers are actually on Oahu. 

Well, here’s the deal, like more than half of them are flat out illegal or genuinely described as “extremely dangerous” by people that have hiked them. I was reading a post about hiking on Oahu by some big time travel influencers and I kid you not, they described half of the hikes on their list as either illegal or very dangerous. 

Well, I specialize in a different niche of hikes…I like to call them “breathtakingly beautiful but very low risk of death” hikes ; )

Easy Hikes on Oahu

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So I’ve labeled this post “easy” hikes, but what exactly does that mean? Well I’ll be honest…when you’re in the middle of some of these hikes you might be thinking “this is NOT easy” but in general they’re all either very well marked and maintained trails (some completely paved), or at least fairly short distances. Most of the hikes on this list are under two miles which I think makes them “easy” even if they feel challenging for a bit. 

Here we go!

Diamond Head

Diamond Head is probably the most iconic hike on Oahu, and that’s partially because of how accessible it is but mostly because of the views. 

It’s a fairly mild hike for such a big payoff. Yes, it’s all uphill, but it only takes 30-40 minutes to climb to the top and once you do, you’ll have fabulous views of Waikiki and Honolulu. 

The entire trail is very well marked, maintained and well traveled so there’s no big “risk” factor.

The most dramatic part of the hike is the tunnel you have to walk through once you get towards the top (maybe 30 seconds or so) and then…the stairs. 

Once you come out of the tunnel, you’ve got two options. Turn right and you’ll go up the largest staircase you’ve ever seen ; ) 

There’s a sign suggesting that you go left instead. If you go left, you still have to climb some stairs, but they’re more broken up so it seems easier. Either way you go, it’s a loop. 

The first time I hiked Diamond Head, we went to the left and then once we were at the top we just retraced our steps back down (most people do this). 

But if you want to do the full “loop” and come DOWN that massive staircase you saw when you came out of the tunnel, then once you’re at the very top, you climb into the pillbox (concrete bunker) and go down the metal spiral staircase to get to it. 

Either way works. 

So here are the logistics…

Increasing popularity has triggered a new reservation system, so you’ll need to plan this one in advance. 

Reservations can be made 30 days in advance here for either just entry or parking and entry. 

If you’re booking the entry and parking options (what I would recommend if you have a car), reservations are made in 2 hour increments starting at 6AM (6AM-8AM, 8AM-10AM, 10AM-12PM, etc.) and you’re asked to arrive within the first 30 minutes of your time slot. 

If you’re just booking entry, reservations are made in hour increments starting at 6AM.

Entry is $5/person (whether you park, Uber, or hike in) plus $10/car for parking. 

If you take the bus/trolley or park in the free spots, you’re going to have to walk pretty far before you get to the actual trailhead. But I believe Uber/Lyft drops you off right at the parking area. 

Either way, you still need reservations. 

I highly recommend booking an early time slot as there is NO SHADE on this hike. 

And if you’re a hesitant hiker and need a little incentive to push you over the edge, here it is…Diamond Head has a line of EXCLUSIVE HELLO KITTY MERCHANDISE. So hike Diamond Head and then you can buy an array of swag with Hello Kitty on it that says “I hiked Diamond Head.” What could be more fun?

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Lanikai Pillbox Hike

There are so many great hikes on Oahu, but I think this is my favorite! 

It’s fairly short, but it’s got a good pay off. 

You’ll find the trailhead on Kaelepulu Drive in Lanikai. All of the parking is on the road and it’s super limited. Be sure to respect the signs of where you’re allowed to be and where you’re not and don’t go traipsing through people’s yards. Because of limited parking, you’re going to want to get an early start on this one. 

Because the view faces east, some people like to go for sunrise, but you’ll definitely need headlamps if you go that route. 

This hike only took me about an hour up and back, but you really have to scramble in some places. The first part is by far the steepest. Most people stop when they reach the first pillbox, but you can keep going if you want to see them all. 

I wouldn’t say this is a “hard” hike at all, but the trail is a lot less defined and cleared than Diamond Head so you have to do a bit of negotiating. 

Makapu’u Point and Trail

The Makapu’u Lighthouse Trail is a 2-mile out-and-back hike. This is just the kind of hike I like. It’s short and sweet with a big payoff of great views at the top. 

From the top, you’ll see Makapu’u Lighthouse down below and spectacular views of the Waimanolo coastline and offshore islands. 

Yes, it’s only a mile to the top and it’s completely paved, but it is fairly steep so I recommend wearing sneakers or strap on sandals. 

Also, there is NO SHADE on this hike so go early in the day and take plenty of water and wear sunscreen. 

Located on the southeastern side of the island, you’ll find the trailhead on the right (ocean) side of the road after you pass Sandy Beach Park and come around the point. The road you turn off on is usually lined with cars and there’s a small parking lot at the bottom. If you come to the Sea Life Park you’ve gone too far.

Last time I did this hike in January, I saw soooo many spouts and whales breaching in the ocean below so be sure to keep an eye out. 

There are plenty of places along the path to stop and take in the view so don’t be in too big of a hurry to make it to the top.

And once you do make it to the top, be sure to go to all of the viewing platforms because they all have different angles. 

The one at the very top is where you’ll look down and see the lighthouse.

Manoa Falls

This is a popular hike because it’s quick (1.6 miles round trip), pretty flat, and rewarding (hello waterfall!). This may be your easiest chance for waterfall gazing. 

Unlike a lot of the shorter hikes on this list that are pretty wide open or arid before leading to ocean views, the trail to Manoa Falls is through a lush, tropical rainforest. 

Also, I would classify this one as more of a “walk” than a hike which makes it great for kids, older people or those who can’t or don’t want to push for a strenuous hike. 

Besides the beautiful scenery along the trail, you’ll be rewarded with views of the 100 foot Manoa Falls at the end. This isn’t a place that you can swim underneath a waterfall though, this one breaks over rocks. 

And just remember…how impressive the waterfall is depends on the amount of recent rainfall. 

Koko Head Crater

Sometimes overshadowed by Diamond Head, the hike up this extinct volcanic crater is still pretty popular, but it’s waaaaay more strenuous than Diamond Head. 

I have included it on this list of “easy” hikes though because the trailhead is pretty easily accessed and it’s a relatively straightforward (and not terribly long) hike. 

But here’s the deal…it’s 1000 steps up railroad ties straight to the top. Talk about a leg burner!

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Ehukai Pillbox

Oahu has a series of pillbox hikes (bunkers from WWII posted in various lookouts around the island) and while the Lanikai Pillbox is definitely the most famous one, I think the Ehukai Pillbox on the north shore is a close second. 

The Ehukai Pillbox Trail is located just off the famous Sunset Beach on Oahu’s North Shore, right behind Sunset Elementary School. 

You’ll turn into the parking lot and there’s a row of parking in front of the park (don’t go through the gates into the school yard). 

The trailhead is just behind where you park. There’s only a dozen or so parking spots here, but there’s plenty more across the road. 

The trailhead is easy to find. From the parking lot, it’s a well-trodden path that quickly starts to ascend through the forest. 

The hike is about 1.5-miles round-trip (about a 30 minute climb to the top) and leads you to two military pillboxes (or bunkers) built during World War II. 

These structures were originally used to defend the island from potential attacks. Today, they serve as historic landmarks and provide an epic vantage point for hikers. 

From the top you’ll be treated to sweeping views of the North Shore’s golden beaches, lush hillsides, and turquoise waters. 

And the pillbox itself is a fun spot for photos. It’s covered with colorful graffiti art from local artists. 

About the trail itself…The hike is a moderately strenuous climb at the beginning, with some steep sections and rocky terrain and plenty of tree roots, but there are ropes to help you out in the tricky places. If you’re in decent shape, you won’t have any trouble, especially because it’s a pretty short distance. 

That all changes though if it’s been raining. Even a slight drizzle and the trail gets SUPER slick to that point that I would not advise attempting (ask me how I know ; ) 

But if it’s the only time it fits into your schedule and you’re determined to make it work, just go slow…use the ropes, and plan to get a little bit muddy. When descending through the tricky bits where there are no ropes, sometimes I opt to use my hands and “crab walk” instead of risking a fall. 

And it’s good to know…there are restrooms at the park at the trailhead with running water so you can wash up after. 

Maili Pillbox Hike

If you’re staying in Ko Olina (Aulani, the Four Seasons, Marriott Beach Club, etc.) this hike isn’t too far away. 

Besides beautiful ocean views, what sits this one apart is that the pillbox was painted PINK to celebrate Breast Cancer Awareness Month several years ago. 

Kaena Point Trail

This is probably one of the less traveled options on this list, but if you’re spending time on the west side, then you may want to check it out. 

It’s at the absolute end of the road on the west side, and the trail is dry, rugged, and pretty isolated. 

There just aren’t too many people that make it out there. It’s mostly because the road doesn’t connect around the island. 

The trail goes about 2.5 miles out and it offers great views of the coast, but it’s very arid so bring plenty of water. The tide pools below may look enticing, but it’s just so isolated that I recommend staying out of the water. If anything should happen, there’s just no one around to help.

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P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable. 

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan. 

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too. 
Get that info >> HERE