Trip of Men 2026

Theme |

Sailing on Lake Superior


TripMaster |

Tolton


MVP |

Captain Alec

This was our 20th year doing these trips (2006 in Killarney was the first trip and we’ve been going strong ever since).

We missed a couple years as you can see in the post record, so it’ll be a couple more years before we’ve completed our 20th trip, but well, it’s all pretty awesome.

For 2026 we added an honourary member/conscripted Alec Smith to join us as our chief procurement officer and Captain. Alec was kind enough to use his connections to get us the use of a 40ft single hull sailboat named Bella (and her tender named Stella). We spent 4 nights on the North shore of Lake Superior moving each day in every type of weather except snow: blistering sun/dead calm, to multiple thunder storms, and much larger waves than I certainly expected on a lake! Alec introduced us to Northern Ontario sauna culture and introduced us to many of his friends at various anchorages. Good food, lots of drinks (as usually) and mediocre butter tarts were featured. We all learned at least something about sailing, Tolton didn’t die, Ian never actually puked and Cole made an appearance for a rediculous amount of sushi on his way through to see his parents in Guelph. Great fun. Thanks for joining us Alec!

Quote of the trip came from an interaction between Ryan and Big Jay as we took Stella loaded with 1200lbs of dude from the anchorage to a remote cabin/sauna. After which 3 bad things happened.

Ryan: “I feel like we should have brought life jackets, this is a pretty wide part of the lake”

Big Jay: “I’m not worried about life jackets, I’m worried about running out of gas”

After which, Big Jay cut his toe badly (later requiring stitches), we indeed ran out of gas on the way back in said big part of lake and the marine radio was dead. We perservered (as usual), we all remained in the boat, and Big Jay got stitched up by seriously over-qualified doctors.