I'm really getting stuck on "garage sailing" since it's not, to my knowledge, a common term. I think you need to set it up better to help prime the listener to think of garage sales while talking about things that both "types" could have in common (you'd likely do either on the weekend).
"Somebody told me about garage sailing. So I woke up up early on Saturday morning. And let me tell you, turns out: not as buoyant as they look."
Or maybe like this, with a bridge that makes the listener lean forward a little and listen harder.
"You know garage sails, right? Bad idea, dangerous, stay away. They just sink."
I like a video that turns the camera around and features real people, and these were extra-special in the time before stuff like easy video production and streaming.
But I especially like what the band Cake did with Short Skirt/Long Jacket, where they went around letting people preview the song and give their reactions on camera. And the reactions were... actually pretty mixed.