Gaetan Cloutier is on a journey. The 42-year-old Quebec native left his home in the Canadian city of Nicolet at the end of October on a 1960 Pivar trimaran named Lapis Lazuli with a cat named Cassiopeia to find a way to live.

Anchored in Horn Harbor for the past few weeks, he’s just waiting for the right breeze to blow out on.

When his parents died last year, Cloutier hit a crisis in his life. He felt sick and forlorn, and he decided to use a small legacy to make a big change in his life. He outfitted his old wooden trimaran with a wind generator and solar panel to charge the battery, a small woodstove that suffices in the coldest weather, and a supply of health foods and essential oils for healing, then set out on a voyage to some unknown destination.

When he puts down his anchor, Cloutier paddles to shore in a small dinghy and uses his road bike and pull-behind trailer to sightsee and pick up supplies. He’s filming his journey and plans to make a documentary about...