4 Awesome Oahu Hikes

Our last SAST trip to Oahu was very hiking-centric.  It’s one of my favorite things to do in Hawaii, since the terrain is so awesome and every hike is so different.   I tend to enjoy hikes with a good ocean-view payoff at the end (or during) and with some solid elevation gain.  There are a few hikes that look AMAZING on Oahu (Haiku Stairs–but it’s illegal to climb) that I still want to do.  These are (mostly) easy to get to, and if you don’t have a car, The Bus can drop you nearby.

The Hikes

Diamond Head:  Yes, it’s crowded with tourists from everywhere, wearing flip flops and having no idea what they were getting themselves in for.  But Diamond Head certainly delivers an amazing view of Waikiki and the ocean.  Granted, you’re crowded at the top with all of your closest friends taking selfies, but it’s worth it.  It takes about 30-45 minutes to go up, with a few spots that are narrow and dark, as well as a good number of staircases toward the top.   There’s 2 ways to get to the top at the “Y” in the trail–if you go left, you hike outside up staircases.  To the right is a darker path up a spiral staircase and through the old lookout buildings.  It’s a fun loop and a good value at $1 for walk-ins (recommended) or $5 for cars, but the parking lot is ALWAYS packed.

Diamond Head View
Diamond Head Stairs

Koko Head Crater:  Across from Hanauma Bay snorkeling reserve, Koko Head Crater looms large.  From a distance, you can make out a thin string of people hiking straight up the side of this 1,000 foot crater on a series of railroad ties.  It’s steep, crowded, slippery, and difficult, but the view at the top is absolutely worth the slog.  The trail has some sketchy spots, including a bridge that requires some careful stepping, but you can find side paths.  For some, it can be more difficult going down than going up!  The reward is a 360 degree view of the island that is unbeatable.  Hiking in the morning or later in the day when it’s cooler is recommended.  What isn’t recommended is hiking after eating a giant bowl of Poke (which one of our friends re-visited at the top…ew).  It takes 20-40 minutes, depending on your fitness level.

Koko Head Stairs

Lanikai Pillbox Hike:  Near one of the best beaches in the world (it is!), Lanikai, the pillbox hike is easy and scenic.  You can’t beat it for a little exercise before plunking yourself on the beach for the rest of the day!  You’ll need a car to access it and parking can be challenging–finding a spot in Kailua and walking is a good bet.  The pillboxes are old watch stations and don’t take too long to reach.  The incline isn’t near as strenuous as Koko Head and the hike through the grasses are really nice.   It’s another 30 minute hike to get to the pillbox.

Pillbox Hike

Olomana 3 Peaks Trail:  I suppose I didn’t really know what I was getting into when I first hiked this one, recommended by a friend who once got us lost in Italy on a 10 hour rainy hike.  I should have known…but this is a cool hike, not for the faint of heart.   If you are afraid of heights or steep drop offs, just don’t even think about this hike.  It consists of 3 peaks (obvs) and you do a fair amount of hoisting yourself up steep rocky outcrops with fixed rope lines.  Admittedly, I made it to the 2nd peak before turning back because it was pouring rain and there was no way I was going to be able to get down.  The views are amazing.  Parking is challenging.  But the views are incredible.  It takes a good 1.5-2 hours to get to the first peak.  And then you can decide from there…


What to pack/bring

  • Hawaii is hot.  Bring more water than you think you need, even on a smaller hike.
  • Shoes with grip/traction.  I bring trail running shoes or hiking boots.  I see LOTS of people hiking in flip flops (slippahs).  Leave that to the locals.
  • Snacks for longer/difficult hikes.  I know Koko wipes me out and a small snack at the top is good for the trip down.
  • Sunscreen.  Most hikes are full exposure, and you’ll sweat it off.
  • A fresh shirt/towel/swimsuit, since most hikes are near the beach you can reward yourself with a good swim afterwards!



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