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It was raining, the anchor wouldn’t set, it was growing dark, and it had been a ten hour day. And then the anchor winch (my boyfriend Mike) said really he was tired of resetting the anchor, please. The second night of our first big trip and already I’d failed. The Copelands being just a stone throw from Lund we motored in that direction, but not before watching another sailboat circle into the bay and drop anchor where we hadn’t been able to. Tied up to the dock in Lund I might have cried a bit. I grew up on my parent’s 24ft motorboat. My dad’s idea of the perfect anchorage was no one in sight, sunrise views, and CBC on the AM dial. He would happily anchor in a hundred feet of water on the windward side of an island if that’s what he had to do. I don’t think we ever tied up to a dock for longer than it took to gas up and find a cinnamon bun. My dad slept like a rock all night, and I never once stayed up thinking about the anchor. Now I was the Skipper, my boyfriend the eager crew, and the boat my own (a beautiful Dana 24 sailboat). Mike took my tears well and tried to tell me there was nothing wrong with a dock. The next night in Tenedoes we tried again, the anchor held and the stern tie operation went well. I set the depth alarm and stared at it anxiously. A slight cross breeze tugged us against our lines and all I could picture was the anchor pulling sideways out of the bottom. I didn’t sleep too much, but in the morning we were exactly where we had been the night before, and the scenery was still stunning. I called my mom to say hello and she confessed that while my dad snored at anchor she had popped her head out of the hatch throughout the night carefully lining up trees with stanchions and trying to decide if all was well. Mike and I’s first real trip was almost six weeks in Desolation and the Gulf Islands. We stayed at docks almost half the time. We stayed in anchorages with other boats, the anchorages described in cruising guides. And I slowly relaxed. On windy nights halfway through the night I now prod Mike awake and tell him it’s his turn, before I fall deep asleep and let him be the one with half an eye open watching the trees through the hatch. I had no idea heading out that I would get so anxious, but the trip proved to us both that we can do it. And more importantly that there’s nothing at all wrong with taking the easy way sometimes. Oh and we met that sailboat, the one who pulled the perfect anchoring manoeuvre at the Copelands as we were running away. They were on their way to Alaska and have been cruising for a few decades, he didn’t get any sleep that night, he was sure the anchor was about to drag.