What to Love About Winter Sailing

Oh, the joys of winter sailing!

Through sheer chance (and some poor planning), I’ve found myself doing a lot of winter sailing over the past few years. Every year I hope to make the most out of the summer season, and every year life gets in the way, until suddenly everyone is making preparations for their annual haul when I feel like I’ve barely had a sailing season to speak of. On the one hand, this cycle can be pretty frustrating. But on the other hand, it has shown me the joys of winter sailing, and now many of my favorite memories aboard are some of the coldest.

winter sailing
"With winter sailing, the sky seems bigger and bigger and broader," says Chesapeake sailor Steven Birchfield, who captured this pretty image.
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Last winter, my boyfriend and I got snowed into a tiny marina in Reedville, VA, on our way from Annapolis to Norfolk. I found a certain type of comedy in having to ask the owner if we could borrow his diesel work truck—which we affectionately nicknamed “Bertha”—to go to the only grocery store in town since we had not packed enough food to extend our trip by the several days necessary to wait out the gale. And you might call me crazy, but I also found comedy in the fact that the marina’s showers were in an unheated building and lacked hot water, making for a very rugged shower experience. I even found amusement in the amount of effort it took to break the ice off the lines the morning that we departed after the gale had passed, although my boyfriend who was doing the ice-breaking probably disagrees with that one. Whenever I start telling stories about my craziest adventures, somehow the smooth sailing and sunny days of summer never make the cut, and I instead find myself exalting the sideways snow blowing through our marina in Reedville.

winter sailing
The author's sailboat, Little Wing, on a snowy winter day.

But winter sailing isn’t all about rugged adventure or wild yarns to spin upon returning home. Sometimes winter sailing is leaving refrigerated groceries on deck (since it’s as cold as a refrigerator anyway) only to misstep and squash a dozen eggs into the cockpit floor. Sometimes it’s laughing at the condensation dripping relentlessly onto your head, no matter how many times you dry it before sitting down. Sometimes it’s days on the water that are so calm and quiet that all you can hear are the gentle lapping of the wake, buffleheads flying past, and the toll of a channel marker through the fog.

For Century Club member Steven Birchfield, that peace and simplicity is what winter sailing is all about: “The sky seems bigger and broader in the winter, causing my mind to get lost in thoughts or memories. I think about races we’ve won, good cruises we’ve had, and about how sailing really brings my life peace and happiness.” 

For Century Club member Jayne Durden, armed with merino wool and plenty of layers, “It’s glorious. Winds are usually constant, and you can really have some amazing sails. If you want to duck into a marina, they are usually really happy to see you and have slips readily available.” 

No matter what type of winter day on the water you may have, be it wild or wistful, at the end of it the boat always feels just a little more like home. Light the oil lamp, cook a warm meal, and settle in under the blankets. In the morning, make piping hot coffee, bundle up, and set off on another day. If you enjoy traffic-free waters, empty marinas, and a bit of adventure (and don’t mind a few extra layers), don’t let the “off-season” stop you from making memories on the water.

by Kelsey Bonham