Originally Posted by NCC320
Getting a line on the piling is the tricky part.
You've practically typed a book describing your challenge. I'm pretty confused reading this thread. First off, what sailboat is able to complete a turn when 25 knots is trying to blow them down? None that I've ever seen.
There are a bunch of good answers here. The one answer I like was a few posts up by arf145.
This method will work as well with less work than some of the others. Remember, the windward line controls the boat.
Come up to your slip, don't turn. Put your cockpit right close to the starboard piling. Use your boat hook to pickup your line off the piling and run it through a stern cleat and then around a cockpit winch, and hold it in your hand. You can pick up that line because it's yours and you left it there (like the rest of us do) when you went sailing.
Now let the wind blow you off, it's OK, you're not going anywhere. When you are stern to your slip, switch the one line you have on the boat to the winch on the other side of the cockpit.... Crank the winch until you're stern to your slip, put the boat into reverse .. and back into your slip.