Months of work going into planning big expeditions – here’s an inside-look at how one of the first sail-to-ski trips along the British Columbia coast came to life.

Ben and I toasted our pint glasses at 1:02 AM, a time I remember only because we had to petition the bartender to let us stay past closing. Parked on adjacent stools overlooking the small marina where he keeps his boat, we laughed at our far-fetched plan. Rally a crew, find the right gear, get lucky with weather, sail across an international border, climb up a steep rainforest, and then, finally, ski glacial peaks. Even with the confidence boost of three beers, we knew we needed the stars to align.

But – spoiler alert! – I probably wouldn’t be writing this article if we hadn’t successfully pulled it off, sailing 200 nautical miles north, hiking up 4,000 vertical feet, and enjoying untracked turns above Princess Louisa Inlet. The payday for all our hard work was a handful of laps in a zone rarely, if ever, skied. The skiing and trip at large is a story for another time. This article is about the less flashy but still important component of how we made it happen.

First and foremost, there’s no perfect formula for planning a trip this big. Some combination of luck, skill, and blind optimism is a prerequisite, but the planning process can take on many forms. What works for me may not apply to everybody. That is to say, this isn’t intended to be the bible of trip planning, but rather a loose collection of tips and tricks I’ve learned over the years, that may in turn help you too.

The Idea: Be bold, but stay within your known limits. Sure, the genesis of our trip was a common writers trope – a pipe dream in a bar – but even at the onset we knew it had legs to stand on. Ben Doerr, my co-conspirator, is a licensed captain, experienced sailor, and one of the best guitar players I know. I’m an avid backcountry skier, ex-guide, and have an infatuation with bad ideas. Juxtaposed, our skills make us a qualified duo for a sail-to-ski trip to British Columbia.

Practically speaking, while neither of us had sailed the Sunshine Coast or hiked the rainforest maze up to the peaks encircling Princess Louisa Inlet, we did have ample past experience to lean on, mitigate risk, and problem solve on the fly. Because our goal was a new route, there was no beta to rely on. Instead of reading trip reports we spent hours reviewing ocean charts, strategizing with topo maps, and creating contingency options if things went south.

The Team: The gaps that Ben and I did have in our skills were filled by other members of the crew. Pulling together the right group for an expedition is probably the most important step in the process. Frankly, you can often get away with a suboptimal coat or mediocre meal, but one bad egg can change the course of a trip real quick. Therefore, finding a collective that works well together and could pull their weight is key.

The biggest element I focus on is trust. Backcountry travel relies on partners that can take turns making decisions, leading and following when necessary. With that in mind, my first phone call was Wyatt Roscoe, my ski partner, while Ben reached out to his longtime friend Sune Tamm, who works as a logistics planner for Antarctic expeditions. These relationships gave us trust and well established lines of communication to lean on when things got hairy. We built on that core group, adding Denali guide Hannah McGowen, ex-Olympian Kaylin Richardson, and backcountry experts Sam and Jenna Ovett.

Check out our next Expedition: Part Two: Sail to Ski British Columbia