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How my skydiving weekend in Hawaii had a terrifying ending

A woman is tandem skydiving, her hand is made into a shaka position suggesting she is having fun, and the background shows the Hawaii coast.
Everything was going fine in the air—until it wasn’t. | Source: Courtesy Sophie Bearman

If a friend invites you to keep him company while he’s housesitting in Hawaii, you don’t say no. That’s how my husband, Sam, and I and our pal Nick ended up on Oahu for a spontaneous weekend this November. Our only jobs were to feed a treat-loving calico cat named Tigger and enjoy ourselves.

Sam and I aren’t the type of couple to spend such a trip lying on the beach. Earlier this year, we took six months off to hike the Pacific Crest Trail during the biggest snow year California’s seen in more than 50 years. Nick, a data scientist from Oakland who is always up for an adventure, is our frequent companion on expeditions involving backpacking, rock climbing and mountain biking.

It shouldn’t come as too much of a surprise, then, that we came up with the idea of skydiving. 

Three people posing in front of a skydiving business in Hawaii.
Sam, Nick and the author prepare to go skydiving in Hawaii. | Source: Courtesy Sophie Bearman

“When in Hawaii,” I said, attempting to paint a once-in-a-lifetime picture of us flying over the deep blue South Pacific in order to convince Sam, who was uncharacteristically reluctant about the idea. 

“It’s really safe!” I said, pointing to statistics showing just 1 in 500,000 fatalities for tandem jumps—not bad at all! None of my internet research said anything about losing consciousness in mid-air.

Surf’s Up

In the end, of course, the promise of a new adventure triumphed over my husband’s sense of caution. 

A man surfs with a mountain in the background.
Sam rides a small wave on Waikiki Beach with a view of Diamond Head in the background. | Source: Courtesy Beach Boy Photography

First, though, we had to ride a few waves. (Again—when in Hawaii!) Upon landing in Oahu Friday afternoon, we headed straight for the warm waters of Waikiki Beach. There are countless surf shops along the beach, which is a gentle, ideal spot for beginners like Sam and I. Nick had more experience, but we all three opted for a lesson from Moku Hawaii, paying $60 per person for an hour, which proved enough time for each of us to catch a dozen waves. 

Ever the optimist, I had envisioned surfing until sunset, but my screaming arms prompted an early retreat to the warm, sandy beach. 

A woman rides a surfboard.
The author catches a wave on Waikiki Beach in Honolulu. | Source: Courtesy Beach Boy Photography

We refueled that night with Hawaiian-Korean food: chicken katsu, meat jun—thinly sliced beef dipped in egg batter and deep fried—and rice from Young’s Kalbee, a local favorite that only serves take-out. We ate it at the house, as Tigger purred away.

Stairway to Heaven

Refreshed and ready for another challenge the next morning, the idea of tackling Oahu’s notoriously difficult 10.5-mile out-and-back Moanalua Valley Trail was a no-brainer.

A narrow stairway with tropical foliage beside it on a mountain.
Once hikers reach the peak of the Moanalua Valley Trail, they can see the stunning view overlooking the off-limits Haiku Stairs. | Source: Getty Images

The trail is the only legal alternative to the Haiku Stairs, also known as the Stairway to Heaven, a stunning World War II relic featuring 3,922 acrophobia-inducing metal steps up the side of the mountain that once led to a radio station that communicated with Navy ships. Today, it offers irresistible views of Honolulu and the brilliant blue ocean. The fire department has rescued dozens of hikers from the treacherous stairway in recent years. As a result, it is illegal to hike the stairs, but the ridge trail up the back of the mountain—the one we took—brings you to the same spot.

Two photos of a person climbing a mountain with gear.
The ridge hike up Moanalua Valley Trail is steep and muddy. | Source: Sophie Bearman

A word of caution: This round-trip trek is not for the casual hiker. It took us about eight hours, and we only managed because we had the proper gear, including plenty of water, rain jackets, snacks, trekking poles and, critically, microspikes for navigating the muddy, slippery terrain. The trail, often adorned with ropes to aid hikers, was bare on our visit, making for an added challenge. We saw several hikers, ill-equipped for the gooey red mud, turn back along the way.

But in the end, the payoff was immense: a breathtaking panorama, especially when the notorious Oahu fog lifted and the wind, which had been blowing in gusts as high as 35 mph, eased.

From Sky to Swoon

Then Sunday arrived, time to tandem skydive. We drove to Skydive Hawaii, which operates out of Dillingham Airfield on Oahu’s north shore. After signing waivers that felt more like wills and engaging in a terrifyingly brief how-to-jump lesson, we were strapped tightly to our guides, loaded into the plane and quickly found ourselves at 14,000 feet. I watched as Sam and then Nick tumbled out of the plane and disappeared. Then it was my turn.

A person flying through the air after jumping out of a plane.
Nick free-falls from 14,000 feet. | Source: Courtesy Sophie Bearman

My guide and I crab-walked to the open airplane door. The roar of the engines and the adrenaline made everything seem unreal. We jumped, and my stomach rose into my throat for a second—that roller coaster sensation—then the fall became an otherworldly experience, a thrilling feeling of unbridled weightlessness despite the reality that we were plummeting at 120 miles per hour. 

A woman smiles mid-air skydiving, surrounded by blue sky.
The author and her guide are all smiles before they deployed the canopy. | Source: Courtesy Sophie Bearman

After about a minute of that wonderful flying sensation, I felt a sudden, unexpected wave of nausea as our parachute opened. I went from falling horizontally, with my stomach facing the ground, to hanging vertically. I didn’t like it. What happened next is fuzzy. I remember telling my guide I felt sick, and then everything went black.

A woman lands on the ground wearing a parachute.
Skydive Hawaii employees run to catch the author and her guide as they land, since she wasn’t able to assume the proper landing position with her knees bent and feet lifted. | Source: Courtesy Sophie Bearman

I woke up face up on the airfield, with Sam, Nick and a handful of worried-looking instructors gazing down at me. I had passed out. Photos show my guide maneuvering to land us as I hung limp in my harness. Sam and Nick, who were watching from the ground, couldn’t tell whether I was dead or alive. The guides said that my harness may have been too tight, cutting off blood flow through my femoral artery, or perhaps my mind simply shut down from the intensity of the experience. 

A woman and man hug.
The author gives her tandem guide a big hug after waking up safely on firm ground. | Source: Courtesy Sophie Bearman

I won’t be skydiving again, but I recommend it for the sheer thrill—if you don’t mind spending around $500 per person.

I was a little weak post-jump, so we spent the rest of the day watching surf pros conquering waves at Waimea Bay and the Banzai Pipeline before paying a visit to Matsumoto Shave Ice, where flavors and toppings ranging from ice cream and condensed milk to my favorite, sweet adzuki bean. The following day, we were back at work.

We’re looking forward to our next housesitting gig. 

Sophie Bearman can be reached at