Oahu Hikes

I like hiking.  Not so much mountain climbing, like my flight attendant friend Nicole, who dreams and plans on climbing the biggest mountains in the world, but I prefer leisure hikes that don’t take pick axes or Sherpas (although I wouldn’t be opposed to a personal assistant during an afternoon stroll up a hill).  I climbed Mt. Shasta, one of the higher peaks in California, once.  I was supposed to be a leader for a group of high schoolers, but the only problem was that I really had no idea what I was getting myself into.  I’m still alive, along with all the under-agers, thankfully.  That’s even after altitude sickness and a lightning storm that commenced upon descent (awesome, in a scary, my-life-is-in-danger way).

Mt. Shasta

Mt. Shasta

I’ve been trading thousands of feet of snow climbing for warm and sunny Hawaii hikes.  Many people avoid Oahu if they want a more relaxing, less crowded vacation experience, opting for the beauty and quiet paradise of Kauai or Maui, which both are known for having many great hikes.  But, for those of you outdoor adventurers that do find yourself on the most populated of the Hawaiian islands and want to avoid the bustle of Waikiki, you will find more than enough outdoor pursuits to keep your soul happy and heart pumping.

Living there just a couple of months, leaves much for my friends and I to still do, an activity of which is hiking.  Here are some that, if you are visiting Oahu, you can check out.  Some of them I have done, and some are still I’m my Hawaii Tourist To-Do List.

Oahu Hikes

Diamond Head– Within walking distance from Waikiki’s resorts and hotels, the easy 1.5 miles up Diamond Head is crowded with tourists, but worth going once to see views of Honolulu and Waikiki.  I honestly like the hike, although many don’t because it’s so “touristy” (a phrase I mostly dislike, because when you travel, just embrace the fact that you are NOT a local).  I still consider myself a tourist in Hawaii, so Diamond Head should be part of a to-do itinerary.  Prepare to pay $1 entrance fee as a foot pedestrian, and $5 for vehicles, and only cash is accepted.  You can hike in flip-flops.  It’s more of an upward stroll.

Diamond Head, Oahu

Koko HeadFree, and only a short 20-min drive from Waikiki, Koko Head is our go-to hike.  It’s quick, ends in a pretty view, and with enough trips, your end will end in a pretty view.  True story (no photos to keep content appropriate).  The hike steps, train trestle, wood 4 x 4’s.  And lots of them.  I don’t know how many steps, but it is enough for you to hate your life for a solid 15 mins, and that’s if your quick.  Great for a morning cardio workout.  Put your headphones in and go.

Koko Head Hike

Koko head hike Oahu

Makapu’u– An the Eastern point of Oahu, this stroll is one you can take the baby stroller on.  Easy!  The two-mile round-trip walk, has a slight increase, but is all paved.  Boasts incredible views. Keep you eyes open, and if it’s the right season, you will most likely see some whales.

Pillbox– On the Kailua side of the island, and overlooking Lanikai, Pillbox is a short hike, but is a fairly steep and constant increase of elevation.  Takes about 45-60 minutes round-trip to complete.  Check out this website which has directions and amazing photos.

Hiking Pillboxes

Hiking Pillboxes



Waimea Falls– So let’s just say, this is NOT worth your time, or your money.  Crowded and it shouldn’t even be categorized as a hike.  It’s more of a walk, or you can ride a golf cart I do believe.  Too many other tourists, and I’m not a tourist hater.  I’m a tourist!  The walk or ride ends with a small waterfall and swimming hole, that is watched over by lifeguards, and not even stunningly good-looking ones!  I’m just being honest.  If you’re gonna spend $15 to get into the park, which you will if you decide to go, you can’t say I didn’t warn you.  The only reason you may want to check out Waimea Canyon and Falls, is because the botanical gardens are beautiful.

Waimea Falls

Olomana/3 Peaks–  This hike is definitely worth a trip, or a couple.  The views and amazing beauty from one end of the island to another can be more fully appreciated from the vantage point of any one of the three peaks.  I loved it and was in quiet awe.  The hike takes about 2-3 hours round-trip.  It’s off of the Pali Hwy, towards the Kailua side of Oahu.  The steep and narrow ascents and descents are decorated with ropes, placed strategically to assist in the climbing.  If you are scared of heights, know that you probably will be a little scared during this hike, but don’t worry.  It’s almost completely safe:)


olomana hike

Hiking Olomana

And yet to do…

Stairway to Heaven:  It’s kind of illegal to climb Stairway to Heaven, also known as Haiku Stairs, so you must start the hike before the guards show up, which means about 2a or definitely before 3a.  One of my flight attendant co-workers is rad and does all these cool hikes and looks really cool doing it.  I want to be cool like her someday, too.

Stairway to Heaven

(photo compliments of Jessica)

Haiku stairs

(Photos; compliments of Leighton)

Sunrise from Haiku Stairs

Seven FallsThe only reason I know about Seven Falls is thanks to four passengers on one of my flights.  These college guys were enthusiastic, fun, and outgoing, which made it easy for me to ask about their week vacation in Hawaii.  I jealously looked through the photos they snapped of some of their hiking adventures, one of which was this place.  I was told not to go unless I had someone who knew the area and had been before.  Anyone want to volunteer as my tour guide?

And they were supposed to give me a really cool photo of hiking Seven Falls, but the boys didn’t.  But apparently, they are skilled Sand Castle Ar-teasts!

Sandcastles in Hawaii


About the Author Kara

Curious. Bubbly. Creative. Curating a life I don't need an escape from and inspiring you to do the same.

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1 comment
LiveYourAloha says June 7, 2017

I love your photos! I have been to this places and I can say this places are really beautiful! Thanks for sharing!

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