Surf Recon, Squeaky Flip-Flops, and a Luau Surprise: A Day in Waikiki

Today started out like the day before — Jeremy and I were up early and headed to our usual spot: the coffee shop on the beach. There’s something about that first cup of caffeine (or a smoothie foe me) with ocean air in your face that makes 6:00 AM feel like a blessing instead of a curse.

What began as a casual stroll quickly turned into a full-on surf recon mission. We wandered along the soft sands of Waikiki, then decided to explore around the base of Diamond Head in search of a less crowded, more “locals only” kind of surf spot. On the map, it looked like a quick walk. Spoiler alert: it wasn’t.

Somewhere along the way, my Teva flip-flops decided to stage a protest. If you’ve never heard wet Tevas in action, imagine a hyperactive dachshund furiously chewing on a squeaky toy — with every step. It was driving me nuts, so I ditched the sandals and went barefoot. Luckily, the pavement was kind, and I only had to dodge a few suspiciously poorly paved sections of road.

Once we reached the south side of Diamond Head, we found it — waves peeling off the reef, a few locals walking up from the beach with boards under their arms and smiles on their faces. Surf paradise. We chatted with a couple of them who gave us the inside scoop on the break and the vibe. It was quiet, beautiful, and definitely going on tomorrow’s agenda.

By now it was around 8 AM, and just as the rest of the island was waking up, the skies opened up in true tropical fashion. Jeremy and I stood on the side of the road waiting for our Uber, rain mixing with saltwater and the faint satisfaction of having found something cool before the day had even really started.

Back at the house, the group was up and in various stages of caffeination and motivation. Jeremy was ready to get back out in the water — immediately. Meanwhile, everyone else looked like they were considering a slower, more shampoo-forward kind of morning. When Daren said he needed to shower first, I took that as my cue to grab a board with Jeremy and give this surfing thing a try.

We rented a couple of boards right on the beach and headed out. Let me tell you: I thought I had decent balance. Paddleboarding last year had already humbled me, but surfing really sealed the deal. I spent more time falling off the board than on it, and just paddling out felt like trying to climb a greased waterslide. Eventually, I got out to the break, sat awkwardly on my board like a newborn giraffe, and took it all in.

The best part? I didn’t even catch a wave. And I didn’t care. It was just great to be out there, floating in the ocean, laughing at myself, and enjoying time with Jeremy doing something he loves.

After our hour was up, I paddled back toward shore, where I bumped into Daren and Erin heading down to the beach, then Kat, who was deep into a solo audio walking tour of Waikiki. We all reconnected like ships passing in the morning — everyone off doing their own thing, yet somehow still together. Eventually, the three of us (the non-surfing crew) swam and lounged on the beach while we waited for Jeremy and Kat to wrap up their adventures.

The rest of the day was all about chill mode. We did some shopping, grabbed lunch, and prepped for the big evening activity: a luau. Now, I had my doubts — it was being held at Wet ‘n Wild water park, which didn’t exactly scream “authentic Polynesian experience.” But I kept quiet and hoped for the best.

And I’m glad I did. As the sun set and the show began, my worries melted away. The food was surprisingly good, the music and hula dancing were fantastic, and the fire dancers were nothing short of incredible. The host — a local chief with perfect comedic timing — tied it all together with charm and laugh-out-loud one-liners.

On the drive home, we wrapped up the day with a classic group debate: the proper use of a merge lane in a construction zone. Democracy was alive and well in our car that night.

Tired but happy, we all agreed to book a proper surf lesson for the next morning and even committed to setting alarms for an “early” start on Friday. Wish us luck.

Up Next: Group Surfing Lessons and More Humble Wipeouts

Stay tuned to see who actually stands up on a board, who panics in the whitewash, and who ends up just floating happily like a sea otter. Either way, the adventure continues.