At the bottom of New Zealand is another, smaller lesser-known island—lying on the edge of the infamously rough ‘roaring 40s’ winds at the heart of the Southern Ocean. It’s called Stewart Island, a wild and unforgiving place, stunningly beautiful, remote and barren. In 2020, in the thick of the Southern Hemisphere winter (with international travel locked down), I led a trio of sea kayakers on an expedition closer to to home. We set out to see if we had what it took to survive the barrage of weather in an unsupported and unaided mid-winter circumnavigation.

Here are the six biggest lessons we learned along the way.

1. You can always push yourself further

A circumnavigation of Stewart Island is a physically grueling journey. It’s a tough proposition even for the most experienced kayaker. Day after day we battled against strong currents, relentless winds and swells. A routine consisting of over eight hours in a laden 200-pound kayak, pushing it further toward our goal, stroke after stroke, hour after hour.