The first time I tried to pick up a mooring singlehanded in a stiff breeze, I approached from dead downwind in the usual manner and stopped the boat with the pickup buoy right where I wanted it. But before I could get forward, a gust blew the bow off and I had to get back to the helm quickly to avoid major embarrassment.
On the next attempt, I remembered how I’d been taught to pick up a mooring under sail and decided to modify that technique. I approached on a close reach and stopped the boat about 10 feet upwind of the mooring, with the bow pointed about 30 degrees off the wind. As I walked forward the bow paid off slowly, and as the mooring ball disappeared under the stem I reached out, pulled up the pickup buoy as it tapped against the bow pulpit and dropped the mooring pennants over their cleats. It was as easy as it sounds, and now it’s standard practice when I’m sailing solo. Usually, I’ll secure one pennant and then wait for the boat to swing head to wind before leading the other around the anchor and onto its cleat. When it’s blowing hard I’ve had to move pretty smartly, as the bow tends to accelerate as it blows downwind. Much will depend on how much windage your boat has—with our low topsides and long bow overhang, we don’t have as much as a typical modern cruiser. In light airs, you can place the bow closer to the mooring; the trick is to make it pay off in the desired direction. Caveat: each time I’ve done this, wind and current have either been together, or the current has been negligible. The decision to place your bow upwind or uptide of your mooring will be dictated by the way other boats are lying.