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.