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Hiking Diamond Head, A Must Do While On Oahu

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Even in the rain it’s a spectacular hike.

Riding your bike on the Seawall in Vancouver and hiking Diamond Head on Oahu, worlds apart but both are iconic experiences that you must do when you visit either place. Ask anyone who’s ever been to Hawaii and they’ll tell if you are spending anytime on Oahu that you must hike Diamond Head. Well I am no different and besides after all the great food, Mai Tai’s and Longboard Lagers I’ve been drinking I could use a little exercise. I put on my hiking shoes, socks, and I’m raring to go. 30 Days In Hawaii is about to to combine 30 Days To A Better Me, a vacation and a work out all at once. Let the hike begin.

Diamond Head State Monument

Under The Covers by Dawn Chubai

I’m up at the crack of dawn for this hike, partly because I’m up anyway and party because I’m hoping the crowds won’t be too busy. Diamond Head is only a 10 minute drive from the Hyatt Regency Waikiki Beach which is great but unfortunately as I head out the sky is over cast with a bit of rain. No rain is going to stop me though, after all I’m from Vancouver and rain in Hawaii is way better than rain back home.

A rainy wet drive to Diamond Head

I've arrived at Diamond Head State Park

At the base of the Diamond Head is my chance to do a quick review to make sure I’m ready for the hike. I’m guessing many tourists come unprepared and no one wants an accident half way up the hike. I’m ready to go. A quick time check as I want to see how long it takes me to get from the bottom to the top of the crater and back. It’s 8am time to start.

Am I ready for the climb

It's 8am let the hike begin

It starts off pretty nice, a paved walk way among tropical trees and only a slight incline. Easy. Not so fast Marc, this is a crater I’m hiking not the seawall. Soon the real hike begins. The path appears to be carved straight from the crater and even though it is raining out it’s not too slippery. It may not be slippery but it is steep, I start to feel the burn in my recently unused thighs and my breathing is a little Huff & Puff.

an easy start to the hike

the real hike begins

at the early part of the hike

If I look up I can see how the trail winds it’s way up the side of the crater. If you look closely you can even see some of the people ahead of my on the trail far above. Believe it or not I’m passed by many people coming up and down who are jogging this hike. It’s obviously not their first time.

look at the winding trail with people above me on Diamond Head

look at how steep the trail is at Diamond Head

Along the trail there are tons of spots to stop and look out and back on the crater. It’s majestic and I can only imagine how spectacular it would look on a clear sunny day. So far my knee is doing great and I’m having no trouble navigating this hike at all. oops I may have spoken too soon. Stairs and lots of them. Almost straight up and at the top I walk through a tunnel cut out from the crater through to the other side. If you are claustrophobic this is a bit scary but also kinda cool at the same time. It’s not a long tunnel and you become friends quickly with others on the trail working their way down if you know what I mean, it’s close quarters Smile

lookout point about half way up Diamond Head

Stairs up the trail on Diamond Head

a tunnel cut through the crater at Diamond Head

One more big set up stairs and then I’m near the top. 1 spiral staircase and then I squeeze though a peek a boo slit at the top to emerge at the peak of Diamond Head.

more stairs

spiralling staircase up to the top

a crawl through portal and I'm up top

Amazing. Unfortunately the clouds are blocking the iconic views I was hoping for but it’s stunning non the less. Looking out to the right I can see Waikiki and if I turn left I can look back at the inside of crater. If you look closely at these pics I think you can make it out.

below me is Waikiki beach

inside the Diamond Head crater

It only took me just over 30 minutes from base to peak. That’s not bad at all for a guy with a bad knee about 50 Mai Tai’s in me over the past few days Smile After taking in the beauty it’s time to head back down to the base. If you don’t believe me that it’s steep watch this quick little video.

I can now check off hiking Diamond Head from my bucket list! If you time your visits to Oahu just right you can also check out one of the many Farmers Markets that take place. The KCC Farmer’s Market is the largest one and is actually on Diamond Head Road so you can stop in after your hike on a Saturday morning. I just missed the turn off for the market and traffic was pretty backed up so I wasn’t able to turn around but next time I will pay better attention and get me some fresh fruit after my hike up Diamond Head.

returning back to to base

What a great morning and it’s only 9:30am. I still have the entire day ahead of me to explore Waikiki and the rest of Oahu. Bring it on!

Thank you to my friends at the Hawaii Visitor’s Bureau for helping make this adventure possible. If you want to have your own Hawaiian adventure there is no better place to start than Go Hawaii, after you read this blog series though first.


Dining Out For Life

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About Author

Marc Smith is a former event planner turned vagabond adventurer. He loves strong Americano's, great wine, cold beer and zip lining over tree tops. Formerly of Vancouver, most of Marc's time when not travelling is in Canada's largest city, Toronto. Follow along on his nomad adventures and discover places to stay, things to do and where to eat & drink as he explores the world one city and region at a time.


  1. I see they have the dark areas lite up. When I did the hike, many of the tunnels and dark areas were not lite and you had to “rent” a flashlight at the base. There were several very claustrophobic areas for me. Glad it’s much better now than it was 15 years ago.

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