As a plein air painter and an avid lifelong sailor I experience lots of weather transitions. After a day of quiet solitude anchoring in the protection of Smuggler’s Cove, I vividly remember the dramatic and abrupt change in weather that evening. It was not a transition. It was a rupture. As the sun began to set, the wind whipped up, the seas roared, and my sailboat Karinya bobbed and rolled on its anchor. Days later in the quiet security of my studio, armed with sketchy notes, anxious memories, and unfocussed photo references I began my painting by scumbling in an undercoat of warm raw sienna which peeks through the wind and weather. Painting on a large canvas I try to put the viewer into the wind, the waves, and the weather, in the hope that they might experience some of what I experienced – a feeling of anxiety, despair, and uncertainty. How could it be so rough and windy when the morning was so calm and still? But alas, there could be hope – hope for tomorrow – maybe the red sky at night might just be a “sailor’s delight”.