My Experience Skydiving the North Shore of Oahu

Last Updated on January 26, 2026 by Charlotte

My stomach drops as I watch my friends fall until the specks of their bodies are no longer distinguishable from the sky. I’m fourteen thousand feet in the air above the North Shore of Oahu, and I’m having second thoughts about all my life choices up until this point. Skydiving had been on my bucket list for some time. But imagining going skydiving, and actually doing the skydiving are a totally different beast.

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Preparing For Takeoff

But first, let’s back up a bit. We’re at Skydive Hawaii, a locally owned and operated tandem skydive outfitter located in Waialua on the North Shore of Oahu. Our day has a slow start. Skydiving is entirely dependent on the local wind and weather, and planes won’t go up unless all of the variables are just right. We spend two hours waiting on their large lanai, watching the instructors pack their parachutes, seeing planes go up, and brightly colored parachutes drift down. But then, it is our turn.

We meet our tandem skydiving instructors and we’re fitted into a complicated harness system that firmly attaches to the front of our skydive instructors. It feels similar to how you’d rig an infant in a Baby Bjorn. My instructor has a black motorcycle helmet, and some of the other instructors are in flip flops. To them, this was probably just another day’s work. To me, this is the most daunting thing I’ve ever attempted.

Our walk to the plane feels like a dream sequence. There’s a lump in my throat, and I’m stuck in my head, heart pounding, thoughts racing. We can barely hear each other speak over the roar of the propellers. On the plane, we’re packed onto two long benches stretching from the plane’s front to the rear like sardines in a can. Then the plane takes off.

Once the plane is airborne, my nerves calm a little. The lush green horn of Ka’ena Point grows farther and farther away. I can see all the way to the horizon, to where the ocean meets the sky. Then, each of our instructors securely straps us in, and double checks the harnesses. I’m at the back of the plane, so I can’t see the full view of my friend’s jumps. I only hear their screams. Until the screams are too faint to hear.

The Jump

Now, it’s my turn. I’m perched at the open door of the plane. We’re surrounded by the puffy white clouds, so high up that the land below looks like a patchwork quilt of green and red, and brown. The wind whips my face, and my neatly braided hair rips loose of its plait. My instructor wiggles us around so that our backs are to the open door.

“You said you wanted to do some flips?” he says, “I’ll count down, and then we’ll jump”.

His words are hard to pick out among the noise of the plane engines.

“One…Two…”

He launches us backward, and the air rips the scream out of my throat. We’re flipping through the air. I see the mountains, the ocean, the sky, mountains, over and over in quick succession, my field of view blurring together.

My hands are white-knuckled. I’m gripping my harness as if the tighter I hold, the less we will fall. Finally, we even out, belly toward the ground, and excitement and adrenaline ebb away my fear.

Freefall

In my sleep, I’d had many dreams of flying. And oddly enough, skydiving feels exactly the same way. In the air, I start to explore what I can do. Reaching out my arms to either side, I dip one shoulder to bank and turn.

I try swimming through the air as if I was paddling breaststroke in a pool. When I open my mouth to laugh with the joy of it all, the rush of the air fills up my cheeks, my lips flapping against my teeth. But I don’t care. I’m having too much fun.

From this perspective, I take in the majesty of the mountains and the sea. Mount Ka’ala is fringed by a skirt of clouds. I see the darker blue of deep water, and the dusky shadows of the reef, all contrasted by the aqua blue of sandy bottoms. I’d never before seen across the whole island in one view. It feels like I can see over the edge of the world from here.

I’m yanked from my thoughts as our parachute releases, instantly curbing our freefall. My instructor uses two handles to direct our descent. The harder he pulls on one of the straps, the tighter our spiral.

He asks if I want to take a turn at “driving”, and I do. I pull on the left handle. We gently arc through the sky as if tracing the outline of a half moon. I pull harder, and our spiral descent accelerates.

The instructor takes back over the steering as we draw closer to the ground. I love this portion of the flight. We peacefully glide along the shoreline, our shadow chasing us along the on ground.

The Landing

The runway and airfield come into view and we coast toward a large grassy field. The instructor tells me to lift up my legs into a pike position so he can handle the landing. I am totally happy to oblige.

We scoot across the grass and our parachute drifts to the earth behind us. My muscles are spasming with adrenaline, and a layer of salt coats my skin. My first thought is, “I want to do that again!”.

On our way out, we each get a certificate of achievement. I text a photo of the certificate to my family with the tagline: “Surprise, Mom! I went Skydiving!”.

How To Plan Your Skydiving Adventure in Hawai’i

I chose to dive with Skydive Hawaii, primarily because of fantastic reviews from friends who had skydived with them previously. Skydive Hawaii has been locally owned and operated since 1984. They have some of the most experienced Tandem Instructors in the world. I’ve personally met the family that owns this company and can reaffirm their commitment to safety.

Skydive Hawaii Tandem Skydiving

Hours of operation

Skydives reservation times are available from 7:00am to 3:00pm every day of the week. However, I recommend that you set aside a full day for this activity in case of delays from other air traffic, weather conditions, volume of customers.

You should plan to be on site anywhere from 2-4+ hours.

Tandem skydive tours

Two tour types are offered: a 14,000 ft drop and a 20,000 ft drop. Pricing varies, with some discounts provided to students, military, and groups. You can check the most up to date pricing on the Skydive Hawaii website here.

Photo and video packages

I highly recommend getting the photo package for your skydive. Odds are, you’ll only skydive once in your life, and the photos are something you will treasure forever. Just know, that your photographer is a third person who will jump alongside you and your tandem instructor. This means that the max group size that can fit on a plane decreases for each person who chooses to purchase a photography package.

Disclaimer

Skydiving poses an inherent risk, and you should be in good physical condition and not have a fear of heights if you choose to try this activity. If you get to 14,000 ft and decide you don’t want to jump, it is totally okay to ride the plane back down.

Looking for more adrenaline in Hawaii?

If jumping out of a plane isn’t enough, check out our experience cageless shark diving on Oahu — it’s another wild way to face your fears and connect with the ocean.