Diamond Head is probably the most iconic hike on Oahu, and that’s partially because of how accessible it is but mostly because of the views. 

It’s a fairly mild hike for such a big payoff. Yes, it’s all uphill, but it only takes 30-40 minutes to climb to the top and once you do, you’ll have fabulous views of Waikiki and Honolulu. 

Here’s everything you need to know…

Hiking Diamond Head

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The entire trail is very well marked, maintained and well traveled so there’s no big “risk” factor. The most dramatic part of the hike is the tunnel you have to walk through once you get towards the top (maybe 30 seconds or so) and then…the stairs. 

Once you come out of the tunnel, you’ve got two options. Turn right and you’ll go up the largest staircase you’ve ever seen ; ) 

There’s a sign suggesting that you go left instead. If you go left, you still have to climb some stairs, but they’re more broken up so it seems easier. Either way you go, it’s a loop. 

The first time I hiked Diamond Head, we went to the left and then once we were at the top we just retraced our steps back down (most people do this). 

But if you want to do the full “loop” and come DOWN that massive staircase you saw when you came out of the tunnel, then once you’re at the very top, you climb into the pillbox (concrete bunker) and go down the metal spiral staircase to get to it. 

Either way works. 

So here are the logistics…

Increasing popularity has triggered a new reservation system, so you’ll need to plan this one in advance. 

Reservations can be made 30 days in advance here for either just entry or parking and entry. 

***Want to save major $$$ on your trip to Hawaii? I get asked ALL the time how I’m able to travel so often to Hawaii and stay at really nice resorts. Well, my favorite travel hack is cashing in points to score free airfare and free nights at some of Hawaii’s most high end resorts. Read my full guide on the exact system I use to max out credit card rewards here. Seriously, it’s going to save you soooo much money.

If you’re booking the entry and parking options (what I would recommend if you have a car), reservations are made in 2 hour increments starting at 6AM (6AM-8AM, 8AM-10AM, 10AM-12PM, etc.) and you’re asked to arrive within the first 30 minutes of your time slot. 

If you’re just booking entry, reservations are made in hour increments starting at 6AM. 

Entry is $5/person (whether you park, Uber, or hike in) plus $10/car for parking. 

If you take the bus/trolley or park in the free spots, you’re going to have to walk pretty far before you get to the actual trailhead. But I believe Uber/Lyft drops you off right at the parking area. 

Either way, you still need reservations. 

I highly recommend booking an early time slot as there is NO SHADE on this hike. 

And if you’re a hesitant hiker and need a little incentive to push you over the edge, here it is…Diamond Head has a line of EXCLUSIVE HELLO KITTY MERCHANDISE. So hike Diamond Head and then you can buy an array of swag with Hello Kitty on it that says “I hiked Diamond Head.” What could be more fun?

More Photos from the Diamond Head Hike

P.S. I travel to Hawaii multiple times a year, and let me tell you a secret…I do most of it for FREE using credit card points and miles. 

I have a somewhat intricate system that I’ve fine tuned over the years to maximize earning points and how I cash them in, but the short version is:

I use THIS Marriott Bonvoy Boundless card for free Marriott nights. The sign up bonus alone on this card will get you 3 (sometimes 5!) free nights at hotels in Hawaii like the Sheraton Maui, Royal Hawaiian (Oahu), Sheraton Kauai Coconut Beach Resort, and the Waikoloa Beach Marriott (Kona). 

And I use THIS Southwest Premier Rapid Rewards card for free flights on Southwest. The sign up bonus will get you at least one round trip flight to Hawaii (possibly two depending on where you’re flying from). 

The combo of these two cards will have you most of the way to a free trip to Hawaii right out of the gate. Again, you can sign up for the Marriott Bonvoy Boundless >> HERE and the Southwest Premier Rapid Rewards >> HERE
And if you’re really serious about getting into the travel hacking game, read this post for a more in depth look at how I maximize credit card points to book travel.

P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable. 

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan. 

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too. 
Get that info >> HERE