When I first received the invite for a Wilderness Collective trip I had many reactions, which were, in no particular order: “I haven’t camped since I was six”, “I hope the people don’t suck”, and “it’ll be nice to go on a pleasant, Instagram-worthy tour off the coast aboard a yacht in order to roast marshmallows on an island”. Our destination would be the Channel Islands archipelago, eight land masses situated over 30 miles seaward from the shores of California’s coast. They’re home to some serious history. The oldest evidence of humans existing in North America and the oldest known evidence of seafaring in the Americas were discovered on the Channel Islands. We would stay on Santa Cruz, the biggest of the eight isles, where scenery is rugged and scrubby, where wild foxes dart in and out of thick, dry bramble and up rocky hillside facades of neutral sun-dried reds, blanched greens and dusty khakis. The multi-faceted trip would not, in fact, be about yachts and butler service. I didn’t know that yet.

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Wilderness Collective founder Steve Dubbeldam, at once jovial and completely relaxed, picked me up at my hotel before dawn. First stop: a secret coffee bar just inside the garage entrance of a private loft in LA’s Arts District, where we met up with most of the our sailing companions — a group of about a dozen entrepreneurs, ad men, writers, photographers, marketing execs, etc. — for high-test coffee, breakfast burritos and tentative small talk. Shortly we all loaded into the van and shot northward toward Oxnard, where we would kiss the mainland goodbye. (Unsettlingly, I was the only one wearing glasses — was I to be the Piggy to WC’s Lord of the Flies?)

Kayak Adventure Packing List

UGG Footwear

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You need something comfy, and your footwear should be proven to last in the conditions you’re exposed to. UGGs are made to be worn by the water, and the Fall 2013 men’s line boasts myriad styles — including some, like Oxfords and moccasin slippers, you wouldn’t wear on a kayak.
uggaustralia.com

Apolis Chambray Swim Trunks

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Sure, pack pants. But when you’re camping near the ocean shore, it’s all about economy — don’t waste time pulling pants on and off. Wear these soft and stylish boardies 24/7 and be ready to hit the waves at a moment’s notice.
apolisglobal.com

Aether Insulated Space Hoodie

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Super lightweight, super scrunchable for packing, water resistant and warm as all hell. It’s even cut really well. This is the ultimate lightweight insulated jacket, and perfect for shaking off the post-ocean chill.
aetherapparel.com

Camelbak Eddy Water Bottle

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This little guy is just right for drinking on the high seas. The integrated straw means you don’t remove a cap and chance sloshing water about. Bite the straw end, which flips securely closed, bite, drink.
camelbak.com

Hobie Mirage Island Tandem

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A two-man, dual-outrigger kayak with an 18-foot sail and pedal drive. Everything you’ll need to motivate you and a friend — and a considerable amount of gear — out to yonder islands in eye-catching style.
hobiecat.com

Nemo Rhythm 25 Spoon Shape Sleeping Bag

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Folding down to a compact capsule, this bag delivers big. It’s very warm, but sheds excess heat, and shaped perfectly to allow side sleepers the torso and knee room necessary for maximum comfort.
nemoequipment.com

Nemo Astro Air Ground Pad

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2.5 inches might not seem like a lot, mattress-wise, but compared to the ground this pad is a cushy cloud. And really, it’s as comfortable as a regular mattress — the chambers inflate and maintain cushion and support with ease.
nemoequipment.com

Watershed Colorado Dry Bag

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Squeeze the air out, zip this sucker shut, buckle it down and water just ain’t getting it. You could fill this bag with baking flour, seal it and drag it behind your boat and get to baking when you land.
drybags.com

Snow Peak SnowMiner Headlamp

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Especially if you’re camping somewhere without electricity, this guy’ll come in handy. There’s a dim mode, bright mode and emergency flash mode and a hook for hanging in your tent.
snowpeak

Aether Riptide Rash Guard

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If you’re surfing, you’ll need this. If it gets a few degrees colder on the high seas, you’ll need this. If you want to look like a superhero, you’ll need this.
aetherapparel.com

When we arrived at the marina Steve plopped down a dozen dry bags, each with a custom-printed nametag hand sewn into the handle, each full of gear sized to the individual for us to use and keep. In violation of the rules on most WC trips (“digital detox” is part of the experience), I was able to take my phone and camera along in the interest of documenting our travels, so I wrapped my electronics securely and hoped the bag would truly keep them dry. With that we moved on to wetsuits — a costume change I, still picturing a fully stocked yacht, thought odd. Besides, I’d never been in a wetsuit before. I’ve never surfed; I’ve never done much sailing. I expected the wetsuit to force me into a Frankenstein’s monster-style lumber, but instead, I immediately and automatically assumed the quasi-bowlegged stance of a seasoned surfer that took weeks to wear off. I was ready. Kind of.

It turned out we needed wetsuits because we weren’t being sailed to the Channel Islands. We were sailing there. In kayaks. Steve and a couple others piloted a classic Hobie Cat, but where I expected a cabin cruiser to be moored were four slim, brightly colored two-man crafts, complete with outriggers, tall masts and plasticine sails. Pedal drives (oversized salad-tong-looking mechanisms) sat in the footwells so that in the event of a windless time at sea kayakers could recumbent-leg-press themselves around. Undeterred by the prospect of a little extra legwork, we paired off, one experienced sailor with one unexperienced sailor. This afforded me the opportunity to quickly befriend Steve’s co-conspirator and our cook for the weekend, Chris, while we set to loading our kayaks and the support boat (a small fishing boat with a motor that carried our food and such). We stuffed moisture-sealed, pre-made lunches into watertight compartments like they were bricks of coke, slapped on a heavy helping of sunscreen, and shoved off for what we were told could be a trip of three to nine hours. Gilligan jokes notwithstanding, this was no three hour tour. With almost zero wind to speak of once we exited the harbor, we resorted to “pedaling” — the entire time.

Somehow the pedaling caused neither strain nor fatigue, perhaps because the physics of walking and the physics of pedaling are closely linked, but I think mostly due to the fact that I was so happy out in the middle of the shockingly beautiful and peaceful ocean. It’s especially breathtaking to stand on the bow of a tiny, red plastic speck in the middle of a monstrous body of water, 15 miles away from — but, more importantly, well over a half mile above — anything else on which one can stand. Chris was an excellent co-sailor, and we passed the time remarking on our being in front of the pack the entire way.

As Santa Cruz, with its huge, sheer cliffs pockmarked with caves, loomed in the distance, the water became rougher, the pedaling became harder and the water sprayed higher and colder. When we finally beached and stood for the first time after eight thrilling hours (yeah, eight), we pulled our crafts out of the way and began taking trips walking our supplies the better part of a mile to our site, where we went about setting up the individual tents provided for use. The few other campers on the island likely thought we — with our matching gear and loads of equipment — were some sort of special forces team on a group vacation.

For dinner I had expected another sandwich and some s’mores. It was here I learned that Chris the Cook was actually “Chef” Chris: what we got was premium charcuterie and freshly prepared white bean chili, with jugs of premixed cocktails to drink. The next morning we awoke early to fresh air, sounds of nature, dawn light and the unmistakable sizzle and smoke of bacon. Not one minute after I’d emerged from my tent, a mug of piping hot French Press coffee was thrust into my hand, which washed down pancakes, fresh off the skillet, accompanied by equally fresh berry compote. Wasting no time, we pulled on our damp wetsuits and headed back to our boats for an afternoon of sailing and surfing on the far end of the island, where waves were breaking high and massive fishing trawlers were anchored, hoping for a bounty. Having never surfed and not wanting to soak up time learning at that moment (and because my feet were burnt beyond what my usual pain threshold tolerated — I had neglected to apply sunscreen to them on our way out), I hung out with our super chill support boat dudes and a few of my travel companions: Chris, a truly incredible photog out of Brooklyn, and Nick from San Fran by way of Australia, who immediately won the “Who Is The Better Nick” competition with his down-under accent.

Later we went to explore our surroundings: sheer cliffs, massive fields of golden grass, rocky hillsides of white and red stone and mossy scrub. We stopped at a cliff that faced directly west, scores and scores of feet above the ocean, just as the sun set in front of us and a massive, dark storm system cycled in from behind. The colors, the majesty, the open space over the uninterrupted ocean accentuated the power and magnitude of the elements we were bare to. Along with my hiking companions, I was in awe of such staggering beauty. Naturally, we all scrambled to grab some new profile pics as the pink light faded to dark.

Returning just as darkness took hold and as more charcuterie was broken out, we were all in full swing friend-mode. Dinner was, once again, astonishing. We were collectively stuffed full of filets nearly two inches thick, wrapped in sweet bacon and cooked to order; broccoli salad that Whole Foods would cry to know existed; baked sweet potatoes; and grilled prawns literally the size of my fist. I hadn’t eaten a meal that fantastic at any point in recent memory, and didn’t for a while after returning home. Indeed, we all ate like kings, laughed and, I think, gradually realized that this trip was astoundingly poignant. We were the Boy Scouts of the 1%: fortunate beyond belief and making the most of every moment, plunged at once into bare nature and high living to explore the essence of life, perhaps.

The next morning we wasted no time gathering our belongings and shoving off, lest we end up on the water for another eight hours. Gladly, the wind was at our backs and the trip back to mainland took half the time as our maiden journey. We sailed past a dozen fat seals sunning themselves and honking on a large buoy, and close enough to oil rigs that we could easily make out the features of workers onboard. Unshowered and exhausted, our hair matted with salt and sweat and with seemingly permanent grins pasted on our mouths, we all partook of a farewell lunch and beer once we hit the mainland. Then we parted ways, each with a new perspective on privilege, the distinct feeling of accomplishment and new friends in every part of the country. In just a couple day’s time I had learned how to pee in a wet suit, that you need to put sunscreen on your feet and how to properly use the terms “rad” and “gnarly” — and also how impressive a Wilderness Collective experience really is.

Because Wilderness Collective is fantastic. Not necessarily just our Channel Islands itinerary or the swag or the food, but the WC philosophy itself. I’ve already said much of what I expected of the logistics, but when I pictured this trip, I figured I’d be a lone journalist among a bunch of rich bros who would talk big about “getting away from it all” and “going off the grid” just because it sounds cool. I expected people with whom I would have a hard time finding common ground. I figured I’d get some great shots, and have a nice story to tell. I was cynical. I was also wrong. Instead, I was taken by the lack of machismo exhibited the entire weekend, the absence of “proving” ourselves and our hubris, but what struck me most — and perhaps only because I have that cynic’s streak — was how terrific my companions were and how much that informed the experience (and certainly vice versa). The group was full of authentic guys who wanted to partake in a lifestyle they otherwise wouldn’t have access to. That’s what Wilderness Collective offers: thrilling adventure, hard work that pays off tremendously, a tinge of risk, great laughs, astonishing sights, exhausting fun, a bunch of great gifts, full bellies and some pretty solid new perspectives, with no room for grandstanding or ego.

When I got to the airport the morning after our return, I remembered that I hadn’t emptied my water bottle for passage through security. I dug it out and drank down the rest. There was still a fine dusting of sea salt on the built-in straw. As I drank I looked back on the weekend and wondered if maybe Steve Dubbeldam hasn’t found the most enjoyable way to cure cynicism. The video above, a new one of which is produced for each WC trip, captures the romance of the excursion — the seafaring, what it takes to fully appreciate the glory of the whole trip — and also serves as a soft commercial for the trip sponsors. But on the island we explored more than great “stuff”. We explored being happy and content and excited about every minute of the day, and I’m pretty sure that’s the key to not being a sucky person. So definitely go on one of the WC trips. It’s worth it for the sights and sounds and eats and gear and for the story. But these trips, while they lean heavily on disconnecting from all things digital, are really more about being authentic, about putting everyone on equal ground where they can exist through the same incredible, epic — yes, epic — journey together.

UGG Australia sponsored Wilderness Collective’s trip to the Channel Islands and invited us along for the ride. Their Reclaim the Day campaign is all about seizing the moment and squeezing every last drop out of an experience, which lines up with the WC philosophy perfectly. With oxfords, lace ups, cobbled shoes and more, their new men’s line goes far beyond fuzzy boots (but those are there too). Check out the Fall Collection and more at uggaustralia.com