Funny Sailing Hats

Sailing has been defined for generations as the fine art of slowly going nowhere at great expense, and one sailboat-owner forum thread adds that you do it cold and wet. The humor runs both ways across the dock. Powerboaters call sailors blow-boaters or snailboaters, and sailors answer with stinkpotter. Good Old Boat's George Bollenbacher notes that anyone in a hurry to get somewhere by water would own a powerboat, while sailors purposely choose a method of locomotion outmoded in the early 19th century. The casual side of the sport is beer-can racing. At Richmond Yacht Club the Beer Can Cup runs Wednesday evenings from April 1 to September 30, with 85 boats signed up for 2026, about 60 racing on May 1, and no official scoring. The rule of that crowd, as Latitude 38 reports it, is to take nothing other than safety too seriously. And the old saying goes that only two sailors never ran aground: one never left port, and the other was an atrocious liar. This is sailing humor, separate from the pontoon-and-powerboat jokes of Funny Boating Hats. Every design is custom embroidered on an unstructured dad hat, for the skipper, the crew, or whoever pays for the slip.