William Woodward on Traveling the World, Wearing Walter Sky & Always Saying Yes

Avid adventurer, photographer and filmmaker, William Woodward (commonly known as @wheretowillie) is living the dream-worthy lifestyle of a nomad with the help of his trusty confidante, a 1990 VW Vanagon named Ruby. And while Willie has traveled to seemingly every corner of the globe, he most recently set sail on a cross-Pacific trip to Hawaii from Washington and field-tested a few of our products while doing so (some of which were already part of his kit). To learn more about the transformative journey and how his Walter Sky essentials held up, we managed to get Willie on the phone during his drive up to Portland just a few days ago to meet up with friends.

Can you tell us a bit about how “Where to Willie” began? 

Where to Willie started on a solo backpacking trip back in 2010, slightly on the predawn of when cellphones worked internationally, so I set up a blog to update my family on where I was at and what I was doing in the world. I would stop into a little internet cafe, write up my experiences and let them know I was still alive somewhere. After getting back from that trip, I knew I wanted to experience more places and share those moments. After another attempt to put my engineering degree to use, photography had become a huge part of my life which led me to leave that job & dive headfirst into traveling full time. In doing so, I bought a 1990 VW van and built it into an adventure mobile. I had committed to taking photography from my weekend hobby and turn it into a full-time business.


Where have you been thus far and where would you like to go next? How do you decide?

Some of my most fond memories have been up in the Himalayas in the spring. But I genuinely love being in any mountains, whether in the states or elsewhere in the world, and this desire to be in the backcountry has definitely led me to do a lot more photography. You can find me doing all sorts of outdoor activities, and while skiing and climbing are my personal favorite pursuits, I’ll say ‘yes’ to pretty much anything. I’m a glutton for trying things I’m not qualified at. I even lived on a kayak in Greece for a month. 

We’d love to know more about your recent trip to Hawaii.

I prepared under the wing of Captain Eric (a friend and sailing savant) for nearly a month in Seattle. I met Eric through his sister, who I’ve worked alongside in the past, so I’d always sail with him whenever I was passing through — but we both wanted to embark on something bigger. He did a cross-Pacific tour from Hawaii to Tahiti about 10 years ago and knew the next step would be to take a boat of his own on a bigger sea crossing. We talked about the trip in theory, then COVID hit and our perspectives of the world totally shifted. So, we decided to finally make it happen. I texted him one day out of the blue saying what if we go this summer and he responded yes almost instantly.



How did you first discover Walter Sky?

To be honest, I think I heard about Walter Sky through a targeted Instagram ad. I saw the shorts with a dedicated pocket for a knife and I was hooked. I connected with Nate over Instagram and have been an ultra-fan ever since. What I love about Walter Sky is that Nate is so intentional about the materials he uses and doesn’t do anything just for the sake of doing it. Being on the go all the time, I need something that’s multifunctional so I can go from the rock climbing gym to the coffee shop to a restaurant without feeling like I need to change. I wore plenty of Walter Sky on the sailing trip because it held up, dried really fast and you can go several days (it took us 25 days to cross) without showering while still looking and smelling decent.

Which item from the kit did you wear most on the trip? 

I wore the WS-S02 swim shorts pretty much the whole time, as well as the WS-MH01 zip hoodie when it got a little chillier at night. That was a staple. I also wore the WS-B01 jogger quite a bit at the beginning of the trip but it warmed up enough to just live in shorts.



Do you think the minimalism of the Walter Sky kit complements your nomadic lifestyle?

I’ve grown a serious appreciation for things that go well together. Some would say I’m a mix of being ultra-simple and super flashy — I’ll either wear a simple white tee or a loud Hawaiian tee. But with Walter Sky, I can mix and match and it all goes together really well. I don’t need to think about it. All of the pieces are well designed to work in conjunction with each other.

How do you think Walter Sky compares to that of popular outdoor brands?

As far as the quality of the gear, there’s no question in my mind that Walter Sky is perfect. But because I’m often affected by the elements, I need to layer for technicality purposes, like throwing on a durable shell for skiing. One thing I really appreciate is that Nate wants to know exactly how I use the gear and how I would change it. A lot of bigger brands don’t care. He wants to know how I feel with the clear intent of evolving and improving each and every piece.


What’s next for you?

I’m currently in my van driving up to Portland where one of my best adventure buddies lives, so I’ll get to hang out with some friends and climb quite a bit. I’m also working on a rebuild of my van over the next few months prior to ski season. I’m planning on touring the backcountry in Salt Lake this season, hitting up the resorts come afternoon. We’ll see how everything pans out in the world, but I’m also hoping to get a few bigger trips in the books, as well. I’m just saying yes and going with the flow.



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