Back to School, Back to the Sea

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 University. A perfect collision of knowledge and indulgence. For me, it’s a cocktail of my three favorite things: cruising, learning, and shopping. A dangerous combination for any sailor with a credit card and a to-do list.
Yet despite what the calendar says, fall doesn’t officially start until we sail. The moment we break free from shore, leaving the months of suffocating heat behind, is when the season truly shifts. With global warming constantly reminding us of its presence, we cling to this time—these precious months that end in r—when the water is still warm, the winds are playful, and the days, while shorter, seem to stretch on forever.
It’s not just about shedding the heat. It’s about shedding everything that comes with it. The days of sweltering humidity when you can’t touch the deck without a pair of shoes. The weeks when working on the boat meant a few early morning hours before the sun made it impossible. Now, it’s the time when we can really work—fix the little things, ready the sails, and dream again of open water.
Fall means freedom. It means we can breathe again—literally and figuratively. It means the season of discovery is just beginning.
So, as we pack up our lessons and prep for the next adventure, Dragonfly is getting her wings ready. The wind is shifting, and the horizon beckons.