Apr 29, 2024 5 min read

From Awe to Ouch, My Unforgettable First Visit to Oahu Had It All

Discover my first-time adventures in Oahu, from stunning hikes and surfing lessons to a dramatic fall at Diamond Head.

Hawaii Oahu

My first time visiting Oahu was fun and memorable. Still, it was also somewhat traumatizing—not because of what anyone did or saw, but because of what I did to myself.

Before I discuss what happened to me, I want to focus on the positives and how I enjoyed my trip.

It was my first time visiting the island of Oahu with my family, but my third time visiting Hawaii. My first impressions flying over the island to land were, "Wow, the water is so blue near the beaches." "The mountain ranges are incredible." And "Omg, I get to see all the places they filmed Hawaii Five-0 in Honolulu" (one of my favourite cop shows).

While there are so many things I could talk about from my trip, if someone were to visit Oahu, these two highlights would always be something that I'd suggest.

The first one involves hiking at Ka'ena Point. It's one of the most beautiful, stunning, and craziest weather-changing hikes I've ever done. We arrived on a sunny but cloudy, warm morning. There are two entrances to Ka'ena Point: the Waianae (South entrance) and Mokuleia (North entrance). At the end, there is a protected bird sanctuary.

My family and I chose to hike from the Waianae entrance. Getting to the starting point of the hike started on a dirt road. Now, Hawaii, in general, constantly has changing microclimates. So we figured it rained a couple of hours before we arrived because the dirt accumulated on my cousins' and my sister's shoes weighed us down an extra five pounds each.

I was laughing hysterically because we had extra weight on our feet every eight or so steps. My boyfriend and my cousin's boyfriend had no problems with their shoes. But I think we tacked on an extra 10 minutes getting to the actual start of the hiking trail.

Now, the hike was GORGEOUS! The beautiful mountain to the right and the ocean and rocky shores to our left. We were all mesmerized by the beauty of such a remote location.

Now, remember I mentioned the crazy changing weather? Well, 10 minutes in, it started to get blazing hot, and as a note, there's no shade along this trail. So we took a break and applied sunscreen. At 20 minutes into the hike, it started to mist on us. To be fair, it was refreshing because we were just walking from the heat.

Right after, it was cloudy with a breeze and felt warm again. And, of course, it was pouring rain as we were nearing the bird sanctuary. While soaked, we were lucky to see Laysan Albatrosses and their chicks and explore the area. 

Now, heading back was funny because we went along the wrong trail leading us up the cliff's side. Granted, a rockslide took out a section of the premade path that was supposed to be there. So, people made a makeshift part of the hike to go around the rockslide. We eventually found our way back.

Still soaked, on our way back, the weather changed to a mist and then to blazing heat, so you can imagine that everything we had on us and our clothes were completely dried by the time we got back to the car.

My second highlight is surfing. You can't go to Hawaii without watching the locals surf; most of them have been surfing since they were kids. I've never surfed before, but my sister, my cousin's boyfriend, and I decided we wanted to try.

We had the best experience and still talk about how incredibly fun learning to surf was. We also learned that we took the same surf school as Tom Holland, and my sister was even featured on their Instagram story.

After a safety debrief, they took us to a location on Waikiki Beach, where the water is much calmer and shallower. There, they first taught us how to get up and paddle on the surfboard.

At first, I was having a hard time balancing on the board. After talking to my sister, we concluded that my arms were not in the correct positions. When you stand sideways surfing, your arms should be one in front and one behind, not like snowboarding where they're to your sides.

My sister was the star student that day (we purchased the photo and video package), and they displayed them on a TV screen. The instructors were impressed by her beginner skills. Honestly, I'd go surfing again and recommend learning how to surf to anyone.

Okay, now is the moment you all have been waiting for. What happened to me? Well, I can tell you I'm traumatized from going to Diamond Head ever again.

The hike up Diamond Head was dry and warm. It was less busy because we came right when it opened, but it started to get busy when coming back down. Anyway, it started misting. I was with my sister and boyfriend, and we started heading back down from the top. I want to add that there are metal stairs and railings with no grip or some rubber grip on them (at least when I went; I'm not sure if they'll add it later on).

My boyfriend, about three or four steps ahead of me, had a slight slip on the stairs. He caught himself before falling and said, "Be careful. It's slippery." As he said, I had my phone in my right hand, and as I was transferring my phone to my left hand so I could hang onto the railing with my right hand, my right foot slipped, and I fell hard down two steps.

I have to say I'm pretty agile because I'm short and have played soccer for ten years. So I managed to prevent myself from falling on my back or my head and instead on my left butt cheek. Still, I felt someone grab my arm, preventing me from slipping further down.

However, as I fell, people were coming up and down, and my boyfriend afterwards told me that everyone on the stairs going up or down froze as if it looked like a freeze frame and was silent.

My initial thought was," (insert swear word) please tell me I didn't break my tailbone." It was all a blur at this point, as I was in so much pain. Then, this extremely kind woman was holding my arm, and... at this point, I was in shock, so everything is bits and pieces here, but she told me she saw me and grabbed me because she thought I would have slipped down more stairs.

It took me about five minutes to stand, and I was terrified that I couldn't stand because my tailbone was all I was thinking about. When I eventually got up, I knew I didn't break it because I didn't have extra pain from standing.

My boyfriend, my sister, and I managed to walk down the stairs to a flat area, and I started crying because the shock wore off. The same woman saw us as she came down, and she gave me one of her frozen water bottles as an ice pack for my now bruised butt. I'll never forget her kindness, and I'm forever thankful for her help.

So, my bruise was the size of a grapefruit, and the impact contact point was an inch away from my tailbone. Thankfully, I was okay to sit and walk the next day because that was when we were going surfing!

Oahu will always be a memorable and traumatizing experience for me. So, would I return to Diamond Head? No, but I'd always love to go back to Oahu.

Thank you for reading and make sure to subscribe. We're constantly exploring new destinations and share our stories, tips, and the beauty we discover along the way.

Great! You’ve successfully signed up.
Welcome back! You've successfully signed in.
You've successfully subscribed to The Traveler.
Your link has expired.
Success! Check your email for magic link to sign-in.
Success! Your billing info has been updated.
Your billing was not updated.