January 27, 2023 — I didn’t have the greatest sleep the night before I hiked Diamond Head. I was waiting for a 5:00am alarm that I didn’t want to miss, and I was also stressing about going out on a hike before the sun was up in a place I didn’t know very well. Such are the realities of backpacking solo.
In the wee hours of the morning, before my alarm, I went online and booked a ticket to climb Diamond Head an hour later — between 7 and 8 in the morning instead of between 6 and 7. Another $8.00, but I did feel much more comfortable when I saw the sky lightening as I left my hostel.
I had to run to catch the bus to Diamond Head as it whizzed by the stop before I got there. Luckily, it got held up at the traffic lights and I got on. It’s a short ride to Diamond Head from Waikiki Beach, and I was dropped off at the entrance to the park about twenty minutes later.
To get to Diamond Head from the park entrance, you have to walk up the road that leads to the car park. I was initially concerned that I was literally going to be walking along the side of the road with cars whizzing by me, but I was happily surprised to find that there is a nicely paved pedestrian walkway all the way up to Kahala Lookout, through the Diamond Head Tunnel, to the trailhead. In fact, the park really caters to those that come in on foot because it is so easy to stop along the way and get your first glimpses of the beautiful views that await you on the hike. Kahala Lookout has a small car park/drop-off area but if you’re on foot, you can just stop, stare, and sigh at the beauty in front of you.

From the Lookout, you head through the Diamond Head Tunnel, which takes you inside part of the crater. Walking through here was so cool, and again, very safe as a pedestrian.
Diamond Head requires advance ticket booking with timed entry. I booked my ticket a few hours before I hiked, so you certainly don’t have to plan too far in advance, though I would be more concerned about booking last-minute on weekends or holidays, when traffic through the park may increase and tickets may sell out. Tickets are sent to your email via QR code, and if you don’t have data in the States (like me), take a screenshot of your ticket for park services. As I understood from my ticket, I had to start my hike by 7:30am and I made it in plenty of time, even with the walk from the park entrance and a nice stop at Kahala Lookout. It’s only about 15 minutes to the ticket office from the park entrance.
The trail oscillates between dirt path, rocky terrain, and stairs. There’s so much to see on every leg of this path! Make sure to stop and turn around every now and again; the views all the way up are just fantastic.



It took me about an hour round-trip to hike Diamond Head. I’d actually even go so far as to say that going back down is harder than going up, because it’s a fairly steep downgrade the whole way. Not only are the views from the hike up and the top of the crater fantastic, there’s also lots to see after the summit. You hike through a tunnel as you head up to the summit, then if you follow the signs as you exit that tunnel, you’ll keep to the left. This takes you around to a couple bonus lookouts before you get to the tippy-top of the crater, where you have 360-degree, panoramic views of the whole island. Keep heading “left” after you descend from the summit lookout, and you’ll find the old observation bunkers that the army used when the crater still served as a strategic military station.

You can actually climb down some levels of the observation bunkers, which were expanded during WWII to include communications rooms and mess halls.




On the way back down the trail, I got to experience even more awesome views, which are actually even easier to see because you’re facing out toward them instead of having your back turned as you huff and puff up the mountain.



Although I originally planned to hike Diamond Head at sunrise, I’m so glad I held off the extra hour. Not only did I get to go up in daylight and experience spectacular views of the island throughout the entirety of my hike, I also got to go up at a less busy time. I was talking to one of my dorm mates later in the evening, who had gone up for sunrise, and it was packed. While I wouldn’t say it was ‘quiet’ an hour later, it definitely wasn’t too busy.
I elected to walk back to the hostel after my hike instead of waiting for the bus. It wasn’t too bad of a walk — almost an hour — and when I returned I sat for awhile before deciding I needed to go to the grocery store to see about lunch. As I discovered the day before, eating out — especially in Hawaii, especially for a Canadian — is expensive. I walked down to Safeway and picked up some crackers, a stick of Polynesian sausage, and a few bananas. I enjoyed crackers and meat for lunch and set the rest aside for the following couple of days.
After lunch, I meandered my way back down to the beach and laid out in the sun for another little while.
After the early morning and so much activity during the day, I was exhausted and didn’t feel like doing much of anything. Being concerned about my budget, I wasn’t sure about going out for dinner and was suffering a lot of indecision on that point. I also wasn’t super hungry. And I was really starting to miss home. I had a chat with Mom and she offered to pay for dinner, which I am so grateful for because it was exactly what I needed.
I planned to shower and then head out for dinner. The dorm I was staying in was 10 beds with an ensuite bathroom, and there was no way I was getting in there before dinner. I changed into my least-stinky-least-rumpled clothes and went out for a Mai Tai and some real food (thank you, Mom and Dad). I went to Lulu’s Waikiki, where I had their shrimp scampi with my Mai Tai, and had enough for leftovers that I brought back to the hostel with me and enjoyed the following day.
I left the restaurant just before 7:45pm, right on time for Friday fireworks on the beach. I’d seen these advertised at the hostel earlier in the week and had been thinking that I’d probably miss them because I was just so tired earlier in the day. Instead, after dinner I was feeling more energized and had a lovely time sitting in a little crowd of people watching fireworks go off over the ocean.

So, the day started amazing and ended amazing. I had my first really low moments on this journey in the afternoon, but I pushed and pulled through, though not without a little help from my favourite people thousands of miles away. I’ve always liked the idea that you can hit ‘reset’ on your day whenever you need to and today I did. I went out for dinner and had a nice time, saw some magic in the world with fireworks, and went to bed feeling happy and motivated to keep on keeping on.
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