Jamaica: Surf, Skate, and Simple Joys

Jamaica wasn’t on my radar. Not until Diego Flores—longtime friend, skater, and all-around good soul—reached out with an offer that I couldn’t turn down. “Come surf with the locals,” he said. “Stay at Jamnesia Surf Camp, run by Billy Wilmot, the local legend.” I didn’t even hesitate. That same day, I booked flights for myself and my son Brody.

I didn’t know much going in, other than a few quick details from Diego: waves right in front of the camp, a legit skate park down the road, and the promise of good times. Diego has been working with the locals for years to bring the skate park project to life, and I’d heard him talk about it before—this labor of love for a community that skates hard and lives harder. But more than anything, I was excited to bring Brody along. He’s been skating for years, and I knew this experience—seeing a different culture and connecting with kids his age across oceans and boards—would be something he’d carry with him forever.

At San Francisco airport with Diego, Vu, and Brody.

Diego assured me it was all set. “Just buy the tickets, man. Show up. Don’t worry.” That’s Diego in a nutshell. So we did. At the airport, we met up with Diego and his friend Vu, a YouTuber from San Jose who’s equal parts creative and comedy. It didn’t take long before Vu had us doubled over laughing, and I knew this trip would be unforgettable.

There was just one question lingering: How are we getting to Jamnesia? Diego, as calm as ever, said, “Frog Boss is picking us up.”

I stopped mid-step. “Wait. Frog Boss?”

He smiled. “Yeah, man. Frog Boss. He’s the guy.”

Sure enough, when we landed, there he was—Frog Boss. A big smile, open arms, and an energy that could fill a room. Frog Boss isn’t just a nickname. He’s the real deal—a well-respected local with a heart for showing visitors the best of Jamaica. With him leading the way, I knew we were in good hands.

Frog Boss and Diego Flores.

We made it to Jamnesia Surf Camp and were greeted by Billy Wilmot himself. Billy’s the kind of guy who makes you feel at home instantly. A local legend in the surf culture, his passion for the community and for Jamnesia is contagious. We talked waves—small that day, but with a promising forecast—and I couldn’t wait to paddle out. The warm water alone was enough to make me stoked after months of surfing the frigid Northern California coast.

Frog Boss at the local beach break.

The next day, we loaded up and hit a local surf spot down the road. The waves were playful, and I soaked in every moment of the sun, the salt, and the rhythm of the ocean. After surfing, we headed to Freedom Skate Park, the project Diego has poured so much time and heart into alongside the local skate community. Seeing it in person—smooth concrete bowls, ramps, and rails—was inspiring. Built with hard work, dedication, and collective effort, it’s more than a skate park. It’s a meeting place. A sanctuary. Watching Brody skate alongside the local kids and Diego throwing down tricks brought me so much joy. Vu filmed and documented it all, adding his own energy to the mix, and I could tell this trip was going to leave a mark on all of us.

Brody getting a little session at Freedom Skatepark, Bulls Bay, Jamaica.

What stood out most during our time in Jamaica, though, was the people. The kindness, the joy, the simplicity. Everywhere we went, people greeted us with smiles. Whether it was skating at Freedom, sharing meals at Jamnesia, or exploring beaches with Frog Boss, there was a sense of ease in their way of life that’s hard to describe.

Frog Boss took us on adventures I’ll never forget: beaches with untouched beauty and waterfalls straight out of a movie. Unfortunately, my camera got soaked that day, and I lost most of my images. At first, I was crushed. But then I realized that some experiences are meant to live in your memory—not on a screen. Those waterfalls, those swim holes, and the laughter echoing off the rocks are all etched in my mind forever.

A local girl taking the leap into a swimhole.

The biggest takeaway from Jamaica, though, wasn’t about surfing or skating, it was about perspective. The people here have so little, yet their happiness shines brighter than anything money can buy. They’re present, they’re connected, and they’re alive. It made me reflect on life back home, where we’re surrounded by things—screens, stuff, distractions—but often miss what’s most important. Less is more. The Jamaicans live that truth, and seeing it firsthand was something I hope Brody takes with him as he grows.

Their happiness shines brighter than anything money can buy.

Jamaica taught me a lot. It reminded me of the simple joys: riding a wave, dropping into a bowl, sharing stories with strangers who feel like family. It’s a beautiful place, not just for its beaches and waves but for its spirit. And as we said goodbye to Billy, to Frog Boss, and to all the new friends we made, I knew this wasn’t just a trip. It was a gift.

For everything I didn’t capture with my camera, I’ve got memories to hold on to forever.