As the months begin to bear the weight of the letter r , the world seems to collectively shift its attention. For some, it’s back to school—a return to classrooms, lunchboxes, and the click-clack of chalk on a board. For us, it’s a different kind of schooling. One without walls, where the lessons come from the wind, the water, and the stubborn demands of a sailboat named Dragonfly . Cruisers go to school too, but ours is on the Chesapeake, where summer’s relentless heat finally loosens its grip. It's a strange kind of relief—like peeling off a sweat-drenched shirt after a long August day, replaced with the first crisp breaths of fall. The air turns cooler, clearer. You can feel the change in your lungs before you even hit the water. But before we point the bow south, there's some studying to be done. This month, it’s the SSCA GAM —learning, prepping, gathering tricks of the trade. October brings us back to one of our favorite playgrounds: Annapolis. The Sailboat Show. Cruisers