On The Road

Our Creative Director Toured the Cali Coast in the Coziest Way Possible

The trip involved surfing, fireside poke bowls, and late-night swims. In collaboration with UGG.

By: Jodi Taylor

By now you guys must know how much we love a good road trip. Another thing we love? Nature. Especially our co-founder and creative director, Jake Rosenberg, who, believe it or not, actually used to guide back-country trips around the world. So when UGG—yup, the brand of boots that you religiously wore your entire way through the early 2000s—and Wilderness Collective invited him to join them on a road trip in their native state of California, he agreed without a moment of hesitation.

Not sure if you guys have noticed, but UGG has come quite some way since they introduced their first surf shoe and classic boot that we know you used to beg your mom for on a daily basis until she finally gave in out of pure annoyance. Jake witnessed this firsthand as he traveled the Cali coast alongside pro skaters and surfers, all in his UGG shoes. Sounds like a dream come true, no? What’s even dreamier are the photos he snapped along the way. Scroll through the gallery below to check them out and read through his travel diary—the crew may or may not have had late-night swims in the freezing cold river.


“We flew in to San Francisco and started by driving over the Golden Gate Bridge. Went to Point Bonita to see a view of the bay, get a view of San Francisco, and the Golden Gate Bridge, which was gorgeous.”

“We stopped at Steve Jobs’ house where he grew up and invented Apple in his garage, which was cool. Apple is one of my favorite companies; the brand has been inspiring me my whole life, so that was a very cool moment to get to see that. It’s now a historical site, so unfortunately you’re not allowed to go inside, but that’s where Steve Jobs and Steve Wozniak created Apple.”

“The trip was filled with a whole bunch of different types of people. There were different content creators, there were pro surfers, pro skaters, and it was all in collaboration with a company called Wilderness that takes groups on adventure travel journeys. The purpose of this whole trip was to bring back the original culture, which was surf and skate and the outdoors. Every night, we would sleep in little cabins and make a big fire, which was really fun because that’s what I grew up doing. You know, growing up in Canada, you go camping a lot, and you go hiking, and you paddle—all of that.”

“Before I started Coveteur, I used to guide trips around the world, taking people into back-country situations. This trip was just the best time ever because I have been traveling for quite some time, but I don’t get to travel in that way anymore.”

“This was a great experience, and I got to learn about the entire product line from UGG for men, which I am extremely impressed with. I did not realize how diverse the product line really was. It covers everything. First of all, I think it is the most comfortable footwear I’ve ever worn in the woods, on the beach, and in day-to-day life. The quality of the product is insane. Originally, when I first started on this trip, I thought, you know, UGG made boots, but they make slip-on shoes, they make hiking boots, they make sneakers, and then they make their big comfy-cozy shoes and slippers. They are pretty bad-ass, not going to lie.”

“I pretty much rocked slip-ons the whole trip—just three different versions of those and one pair of sneakers. They are all more or less waterproof and have a great sole on them. I was camping, walking around in the middle of the Redwoods, wearing these big, furry, cozy shoes, and my feet could not be more comfortable. Was I running around and all that? No, I was just chilling, but perfect for sitting by the fire and all that kind of stuff.”

“The next day, after our first night in the Redwoods—we were pulling out of the Redwoods, and there was this monster hill that just went on for miles with a freshly paved road. We were on a trip with skaters and surfers, so they just jumped out of the van and skated the whole hill for, I think, 40 minutes—just a crazy-long cruise down this hill. It was super fun.”

“The guys who were leading the trip, Wilderness, they partner with Verve Coffee. Verve is an amazing coffeehouse—we stopped in Santa Cruz and went to their roasting facility. I’m a big fan of Verve, I just didn’t realize it was actually based out of California. We learned about where they pick their coffee. They took us on a nice tour of their roasting facility, kind of walked us through the process, which was super cool. We met their director of coffee, and she told us all about her travels, which was a lot of fun. And the coffee was spectacular. They get their coffee from nine different countries, so everything 50 miles south or north of the equator, like Ecuador and Costa Rica, Indonesia.”

“I am a big fan of UGG now. They have a very diverse product line. The trip really educated me on the culture of UGG and what UGG represents, which is active adventure, healthy living, comfort, and quality.”

“After that, we went down to a famous surf spot, Steamer Lane, and we went surfing. Before the trip started, they had three custom boards created, which was super cool, by a company called Grain out of Oregon, I believe. They are these hollow wood boards. This awesome kid named Alex Smith was on the trip, a pro surfer from Hawaii, and another guy named Sakae [Patrick]—he is the face of UGG's campaign. They found him randomly on the street. They street-casted him for the campaign, pretty much. Now he has been the face of the brand. He grew up in Japan, travels the world surfing and skating. Alex Smith was the first person I met on the trip—just an awesome guy all around, travels and surfs professionally.”

“Big Sur is one of my favorite spots—it is just a fucking magical place. It’s so beautiful, the vibes are good, the energy is good. It’s amazing. Unfortunately, the bridge cracked recently during all of the rain they got this year. You can only go in one way, and you have to leave another way, so it adds an extra three hours to your trip, but we did it. We drove into Big Sur; it was gorgeous. Then we camped another night in the Redwoods, which was super sick, as it always is.”

“Every night was a lot of fun—it was a pure dudes trip. So it was like set up camp, cracking beers, making fires, and everyone just telling jokes, playing games, and as the night went on it was just rowdier and rowdier and rowdier until people were in the ice-cold river trying to stay in as long as they could, or everyone getting wetsuits on and jumping off the bridge.”

“We went surfing in Santa Cruz, and the lighthouse is very famous. We surfed, then we camped again outside of Santa Cruz, which was super fun. The whole trip was kind of foggy and rainy inland, and then as we headed out to the beach, it got sunnier again.”

“The food was awesome. Felix [Barron] was the chef, he's with Wilderness as well. He drove our van. He cooked the first night—they cooked poke bowls and these amazing charcuterie boards. One night was this amazing Indian-style chicken dish. It was all delicious, I mean, the food was insane.”

“Hearst Castle was a pretty epic stop on the trip. First stop at the Hearst Ranch. They keep the cattle right at the ranch, where they also make the burgers—they’re delicious. We stopped there for burgers, and then we went up to the Hearst Castle. It’s an amazing thing to see, it’s, like, 116 rooms. The only thing is that we showed up and we were in full clouds, you couldn’t see a single thing. That was the only unfortunate thing. The pool was my favorite thing there because it is all 24-karat gold tiling. Insane.”

“After the Hearst Castle, we drove up to Ojai. Ojai is amazing; it’s interior California, not coastal. We stopped at the Ojai Rancho Inn. It ended up having a great pool. We had a barbecue, we played corn hole and got belligerent. So much fun. That was our last night on the trip.”

“From there we drove up to Malibu and went to Malibu Country Mart. Along the way, we stopped at some sand dunes. The guys were just guys and ran up and down the sand dunes, nothing crazy. Then we went to the Malibu pier and went for a long walk.”

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