THE HAWAII & ASIA SERIES PT8
O’AHU, HAWAII
Any adventure seeker tends to have skydiving at the top of their bucket list, and I was no different. Skydiving in Hawaii topped my bucket list.
YOU TEND TO FEEL MOST ALIVE WHEN YOU ARE CLOSEST TO DEATH
Anyone who knows me knows that when I set out to do something, I like to do it right. When I was travelling up from South & Central America, I always wanted to get back to Asia before making my way home. I saw this as the perfect opportunity for two things.
Crossing the date line, which has strangely been a bit of a bucket list thing for me to do. Flying over this imaginary line and immediately losing a day just appealed to me; I have no idea why.
The other thing was a skydive, and I could think of no better place than O’ahu, Hawaii, to do my first skydive. Again, there was no logical reason for this other than knowing I was in Hawaii, a place most of us don’t get to visit.
BATTLE WITH THE WEATHER GODS
I knew here that my fate rested in the hands of the unpredictable weather gods. For people not familiar with Hawaii, yes, it might often be sunny, but skydive weather can be a little hopeful at times. But I signed up for the following day, and lo and behold, it was cancelled.
Now this kick-started the thought of the next few days being the same. Flights aren’t cheap to Hawaii, and I was due to head to Manila in just a few days, so it was make or break.
The SKYDIVING O’AHU, HAWAII LAUNCH
Fortunately, the next morning looked positive. We arrived at the North Shore, and the instructors told us to cross our fingers. A gale was coming in, and it was a race to see if we could beat it. We skipped the small talk, did a quick safety briefing, and bolted for the plane.
Nerves? None. At least, not yet.
I wasn’t at all nervous at this stage, which surprised me, but I wasn’t yet looking out of a plane flying at 18,000ft!
They say a bungee jump is harder because you have to physically force yourself to leap. With a skydive, once you’re in that plane, you’re at the peril of the instructor. Regardless of whether you want to jump or not, he will!
As we gained altitude, the excitement finally curdled into real nerves. The airplane shutter slid up, and one by one, the other divers took a “bow” out into the abyss.
RELATED READ: A HANGOVER & THE 134 NEVIS BUNGEE
THE ASCENT: 18,000 FT
Gaining altitude, the nervousness and excitement really settled in; I was going to go parachuting in Oahu!
The next thing I remember is the airplane shuddering, coming up, and 1 by 1 the other skydivers taking a bow out of the plane.
Jumping out of a plane sounds ridiculous, but you get to a height where it no longer affects you as it should. The ground was 18,000 ft below me, which was a lot easier than the bungee jump, which was 43metres.
THE JUMP: NO GOING BACK
Anyway, out I went, and that’s when the thought hits you. There is no going back, and if something were to go wrong, then that would be it. You tend to feel most alive when you are closest to death! It was here that I could appreciate the beauty of skydiving in Hawaii, rather than anywhere else.
Absolutely, it’s something I would do again and again, but it’s got to have something different to offer rather than just anywhere. I had initially tried to do it in San Jose LINK, above a glacier, which would be incredible.
BACK TO THE ADRENALINE HANGOVER
The second your feet hit the grass, the “high” is unlike anything else. You’re shaking, your ears are popping from the pressure change, and you’ve got a grin on your face that you couldn’t wipe off if you tried.
We sat around the hangar for a bit, watching the next group of “victims” get suited up. It’s a strange feeling watching people go through the same pre-jump jitters you just conquered. I grabbed a greasy burger nearby. Food always tastes better when you’ve just cheated death and processed the fact that I’d just ticked off a major bucket list item before my flight to the Philippines.
BACK TO THE PHILIPPINES
FINAL THOUGHTS
Looking back, I’m glad the weather gods played hard to get on that first day. It made the eventual takeoff feel earned rather than just scheduled. People often ask me if skydiving is “scary,” and my answer is always the same: the fear lives in the waiting. Once you’re out the door, fear doesn’t have room to breathe; it’s replaced by pure, unadulterated presence.
If you’re sitting on the fence about a jump, stop thinking. The “what ifs” will kill your buzz before you even get to the hangar. Just book the flight, get on the plane, and trust the process. You’ll land as a different person than the one who took off.
FAQ’s
Is skydiving in Hawaii worth the high price tag?
Look, Hawaii isn’t cheap for anything. But if you’re going to spend the money, spend it on an experience you’ll remember when you’re 80. Jumping over a patch of grass in the UK or the US mainland is one thing, but seeing the entire O’ahu coastline from 18,000 feet is a different league. It’s a “one-and-done” investment in your own sanity.
Which is the best island for skydiving in Hawaii?
O’ahu is the king for this. Specifically, the North Shore (Dillingham Airfield). The scenery is the most dramatic, and the drop zones there are world-class. If you’re on Maui or the Big Island, there are options, but for the “bucket list” version, O’ahu is the only answer.
Do I really need to jump from 18,000ft?
Need? No. Should you? Yes. A standard 12,000ft jump gives you about 40 seconds of free-fall. At 18,000ft, you get over a minute. That extra 20-30 seconds is the difference between “What just happened?” and “I am actually flying.”
What happens if the weather is bad?
Welcome to island life. As I found out, the “Weather Gods” in Hawaii are temperamental. If it’s too windy or cloudy, they will scrub the flight. This is why you book your jump for your first day on the island. Give yourself a “buffer” of 2 or 3 days so you can reschedule if the gales roll in. Don’t leave it until your last day, or you’ll leave disappointed.
NEXT UP
The most scenic train ride in the world! Click to read.
SAFE TRAVELS, DS x
85/229
This post is part of The Hawaii & Asia Series, click to explore or for episode 1 click here.

Question Time
- Have you ever done a skydive or would you like to do a skydive?
- Where would you like to do it?
Let me know in the comments below . . .


















