How My First Trip to Hawaii Pushed Me Out of My Comfort Zone — and Helped Me Conquer My Fear of Water Sports

I went surfing in Hawaii for the first time — here's why you should, too.

Aerial view with surfers and barrel blue wave in ocean
Photo: Getty Images

Despite learning to swim as a kid and always living close to a lake or ocean, I've never exactly been the biggest fan of water. Sure, I'll go in for a quick dip now and then, but anything more than that makes me a) want a nap and b) feel like I'm one badly aimed kick away from sinking to the bottom. And water sports? Forget about it. Other than the occasional (terrifying) jet-ski excursion while growing up, I've long avoided water-based activities at all costs — for both my distaste for the sea and my serious lack of athleticism will inevitably combine in disaster.

However, a few months ago, I got an offer from the Waikiki Beach Marriott Resort & Spa in Honolulu to visit the property and partake in one of their exclusive experiences — including a private surfing lesson led by the neighborhood's legendary Beach Boys, a group of locals who have taken tourists out on the water for generations. As excited as I was at the premise of visiting Hawaii for the first time (especially in December, when I spent most days shivering in a sweater), the idea of going surfing, when I can barely stand on an actual floor without falling, gave me some major doubts. But it was Hawaii, so I, of course, said yes.

Luckily, I had some time to build up to the big event. The resort underwent a big renovation not long ago, adding in two pools, an amenity deck, and a brand-new restaurant, among other changes. So, along with my fiancé, Kurt, who'd come for moral support (and Hawaii), I spent those pre-surfing days exploring it all: eating, drinking, and soaking up the sun to my heart's content. We devoured nachos at the delicious Queensbreak eatery, sipped mai tais by the adults-only pool, and took in the stunning Waikiki sunsets from our suite overlooking the Pacific Ocean. It was as relaxing as could be — until it was time to surf.

Rachel Simon with Surf Instructor in Hawaii
Courtesy of Rachel Simon

I'd watched plenty of people take on the waves during our walks on the beach, and although I admit it looked fun, I couldn't imagine successfully joining them. There was simply no way that my totally uncoordinated, sports-adverse self would ever be able to make it up on a board, let alone stay up on it long enough for it to count as surfing. So when Alika, the Pacific Island Beach Boys instructor assigned to take us out that morning, brought out two intimidatingly large boards and demonstrated how to use them, I listened, but with a whole lot of skepticism.

"I just hope I manage to get up once," I told Kurt as we paddled out, to which he — no stranger to witnessing my constant klutziness — gave me a sympathetic look that clearly said, "that's optimistic." Still, I was determined to not completely embarrass myself, so when we made it to the proper spot in the water, I followed Alika's instructions exactly and positioned myself properly on the board. I gulped as he pushed me forward onto a wave — and then, with unstable legs, I was kneeling. I managed to stand, and then suddenly, I was surfing — actually surfing — even if it was only for a few seconds.

Author, Rachel Simon, taking surfing lesson in Hawaii
Courtesy of Rachel Simon

And it was amazing. Standing on the board, my fears about being out on the water melted away. All I could think about was how exhilarating it felt, and how gorgeous the ocean and beach looked around me. Did I look graceful and cool? Absolutely not — my legs were so wobbly that it was only a few seconds before I teetered over, laughing, into the water. But during that short time, I felt strong and capable, and proud that I'd done what I told myself I couldn't.

After that first run, I went back again and again, high off the thrill of conquering my fear and defying all expectations. Each time, my legs got a little stronger, staying on the board for a bit longer. I even managed to look back at Kurt a few times to pose for some GoPro photos. By the time the lesson ended, I was exhausted, soaked to the bone, and feeling more alive than I had in ages. It was an incredible experience, and one I know I would've been too scared and cynical to seek out on my own.

Although our trip to Honolulu was too short to try any other water-based activities, it left me feeling not only confident, but genuinely excited about the prospect of tackling them back home in North Carolina or on our next beach vacation. Kayaking, waterskiing, wakeboarding — you name it, and I'm down to try it (except for cage diving, which gives me heart palpitations just thinking about it). Will I be automatically (or ever) good at all these sports? Definitely not. But if I'm getting out of my comfort zone and having a blast while doing it, who cares?

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