Editor’s Note: In this series, Off the Beaten Path, we’re telling the stories of outdoor guides and how they spend their time off, individually experiencing the very places they uncover for people every day. We’ll take you on their personal journeys — unearthing natural wonders and calling out the gear they use along the way.

“What do I do on my days off? Some days, I Gorilla Glue the holes in my surfboard,” says Jerry Phillips. Sure enough, his board sports three freshly patched holes, punched last night when Phillips and another guide went surfing after work. “I fell on the first wave, and was floating right in the boneyard when the rest of the set came through,” he says.

Phillips is a guide for Santa Barbara Adventure Company in Channel Islands National Park, a series of five rugged islands rising just off the coast of California. Though the islands can be seen from LA on clear days, their relative isolation from the mainland has allowed them to remain undeveloped and makes them collectively one of the least visited National Parks.

Phillips is just twenty years old. But he’s an assistant manager and respected guide out here. His path to Santa Cruz, the largest of the Channel Islands, has been dense with wild experiences. “As a kid, I didn’t like the outdoors that much. But I liked trout fishing, and that got me outside. Then I liked climbing, and that got me outside even more,” he says. In the middle of a ranger-guided tour in Denali, a match struck in his head: “I looked at the guide and realized I could make a career doing that.”

He was studying psychology at UC Santa Barbara and planned to go to Yale for grad school. “I went surfing for the first time less than a week in. And I remember saying to myself, ‘I’m probably not going to go to Yale.’” He became an active member in UCSB’s Adventure Program, leading backpacking, kayaking and climbing trips, and spent a summer volunteering as a junior interpretive ranger in the Yosemite.

After he graduated, he got a job guiding kayak tours on the island. “My first day out here, I was guiding,” he says. “It’s all common sense. You figure it out.” Now he works on the island five to seven days a week.

He’s taken to the Channel Islands quickly. “Yosemite has a lot of shock and awe. In some ways, the Channel Islands is a quaint national park. You have 200 to 300 people on these islands at a time, max. Yosemite gets six million visitors a year. This is small, sure — but then you get into the ocean and it opens up into grandiose adventure.”

On tap for an off-duty afternoon: a big bite of that grandiose adventure. Phillips suits up in his Xcel Drylock wetsuit, NRS Ion personal flotation device, and Adidas Terrex Voyagers and is pushing his kayak off into Scorpion Bay ten minutes later. As he paddles past the breakers and through the canopy of a massive kelp forest, perched in one of SBAC’s Ocean Kayaks, he points out the gnarliest of the island’s 250 sea caves. “When I’m guiding clients, I spend all my time making sure everything goes smoothly,” he says. “When I’m out here on my own, the fun is getting yourself into the bad spots, and then getting yourself out.”

Getting into a bad spot inside one of these booming caves is a scary prospect, but Phillips seems unconcerned. The solution, again, is common sense. “I just remind myself to stay calm,” he says. “Yes, there’s a chance there’s a rock that will hurt you. But ninety-nine percent of the time, it’s just a lot of water moving around.”

His first so-called bad spot worth visiting is the aptly named Boat Wreck cave. The tide is high, and the swell rolls through the yawning entrance, bellowing and belching spray. Here’s the plan: once inside, he’ll hang a sharp right and wait for a small hole in the back of the cave to funnel a swell into a concentrated wave that he’ll surf through the cave and out its side entrance. “But there’s a big space against the wall to the left — I avoid that because there’s not enough room for both a kayak and a person,” he says. “If you have to bail out, you bail to the right. Oh, and sometimes there’s another wave coming in while you’re going out, so you might get whomped from both sides.”

He paddles in, waits for the swell, catches it, and rockets through the cave, then gets whomped from both sides and eats it. He keeps his cool and lets the massive churning gyre of water pull him right out the cave mouth, then climbs back aboard.

Back at the cave entrance, he chuckles. “Yeah, that got pretty hairy. Don’t think I’ll do that again.” He takes a long look at the swell breaking through the cave. “Well… maybe just once more.”

Later, Phillips ditches the kayak gear, grabs a Nalgene and a book — The Geology and Landscape of Santa Barbara County and Its Offshore Islands — from the guide shack, and hikes up to Delphine’s Grove, a stand of Cyprus trees overlooking nearby Anacapa Island. He sits down in a shady spot and munches on a cookie. “I always have lots of stuff in my head, from working all the time, and when I’m not working, from finding exciting shenanigans to do,” he says. “When I’m by myself, it’s nice to just quiet my mind. That takes more energy than one might think.”

The Watch for the Journey

Montblanc’s 1858 collection was inspired by the adventures watches made by Minerva in the 1920s and ‘30s. The Automatic Limited Edition homages the classic stylings of that brand — cathedral-shaped hands, railway minute track — on a bronze-and-green canvas that’s right at home in the wild. Its green NATO strap is the perfect finishing touch for a watch that an adventure guide would love. Buy Now: $3050

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