The Best of Oahu Hikes
Hands down, without a doubt, bar none: Oahu is the best place to hike. The views are incredible. The hikes range from easy (and gorgeous) to intense (and gratifying). You can always find a great mix of locals and tourists on the trails, and some of the lesser-known trails or rock faces give Oahu a “treasure hunt” vibe.
Most of the hikes are near the water. Perfect for a nice swim to cool off afterward, right?
Olomana Trail Hike
Situated on the windward side of the island, the Olomana trailhead lies on the side of Pali HWY just inside Kailua. The views are supreme, and the first peak (of 3) is by far the best view. I personally think the 3rd peak should only be attempted by serious hikers. It’s dangerous.
Up to the first peak will set you back about 1.5 hours, and you get a sweet rope-climbing experience up the scraggly rock face. Not for the faint of heart!! Don’t look down if you are scared of heights!
Dead Man’s Catwalk (“permanently closed”)
It seems that the private company that owns this area of land tore out the iconic “Dead Man’s Catwalk” concrete plank, but I didn’t let that stop me from having a good time looking out with this awesome view.
Bonus Points if you can get a para-glider to wave at you!!
The Stairway to Heaven/Haiku Stairs (“illegal”)
Be warned that you can accrue a $1000 citation for climbing this hike. Please see this post for more details.
Coming soon: How to climb the Haiku Stairs covertly
If it might rain or did rather recently, please proceed with extreme caution. I hiked this with my uncle, and we both bit the dust a few times on our way down. The trail is slippery wet or dry, but I can imagine it being more dangerous with cascading waters as you ascend or descend. The views at the top certainly are worth it, though.
Diamond Head Volcanic Crater
This was certainly the most touristy hike I did while in Oahu. its heavily trafficked, takes around 45 minutes to the top, and has some of the coolest views of the crater bowl and surrounding water. I would recommend if you are here on a very short vacation.
BONUS: shorter, easier hikes that didn’t make the cut:
Ehukai Pillboxes (North Shore)
Rather touristy, occasionally muddy, but quite a nice view as you ascend through the banyon trees.
Koko Head Arch and Queens Bath