Hiking Oahu, Hawaii

While a Hawaiian vacation brings beaches and surfing to mind, I was pleasantly surprised to find endless trails to hike and explore on my trip. The island of Oahu is incredibly lush, with everything from fir trees to palms lining the trails. The trails themselves are diverse, ranging from steep abandoned-railroad “stairways” up mountains, to ridge hikes, shaded forested paths, and rocky beach paths.

The ridge trail to the first Pillbox in Lanikai

Here are my three favorite hikes, as well as links to extensive information about each.

  • Koko Head Crater Hike (Koko Head Stairs):  By far my favorite of all, this evoked the same steep, railway-staircase feeling that Stairway to Heaven promised (unlike Stairway to Heaven/Haiku Stairs, Koko head is not illegal or closed). It was steep, so expect a hike that feels more like two hours on a stairmaster than a leisurely stroll. The view from the top is absolutely breathtaking, and the fact that you’re climbing an abandoned railroad from WWI makes it pretty damn cool.
  • Lanikai Pillboxes: Another steep one, with another set of rewarding views at the top. This hike is super short in comparison to the others, clocking only a mile and a half round trip. The reviews I read definitely downplayed how steep and rocky this short trail was. The reward was exploring the two “pillboxes” at the top; basically old WWI cement bunkers that have since been covered in pretty graffiti. The view of the Mokulua islands off the coast makes you feel like you could be in a postcard.

At the first pillbox at Lanikai, with the Mokulua islands in the background and a Furious Chicken of a doggers in the foreground. 


  • Ka’ena Point Trail: This one might be one of my favorites partly because of the circumstances (it was a sunset hike on a first date) but that’s also why I highly recommend it. While the first two hikes were crowded during the day and offered spectacular views, the Ka’ena Point trail walks along the rocky shore towards the setting sun. It’s easy to be the only people on the trail at that time, and wish a flashlight, it’s easy enough to get back after sunset. Pro tip: bring a couple of beers or a bottle of wine to enjoy on the rocks – major points winner.


    Photos don’t even do the view at the summit of Koko Head justice…. it’s perfect.


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