While I like to back into my slip (both from how the boat fits and since I single hand, this allows me to get a line on the piling from the helm station as I first reach the outer piling), I belive that, if the cross wind/down wind is very great, there is a chance to loose control in your example...i.e. the crosswind spins the boat around, trapping you into position that you can't escape. You have more control in a bow first approach. The trick is to get into the dock and prevent the boat from drifting down onto the leeward finger pier. You have the avantage of a crew to help with the line and disadvantage that you are on the wrong side for good visability. Here is an idea:
Lead a line from/through a midship cleat (outside the lifelines) forward towards the bow. Have the crew get this on the outer upwind piling or cleat when bow first reaches the outer upwind piling or cleat. This is critical. On board the boat, have the line led back to upwind primary winch, three wraps around the winch, winch handle locked in the winch. Continue with the tail to/through a fiddle block with cam cleat, attached to the forward part of the pushpit stanchion, and with tail continuing to helm station. Pre-rig the line and block(s) (actually the block(s) can be permanently on the boat). You take in slack as boat moves in, crew moves to winch and winches in the line to hold boat up wind initiatially. Once boat pulls against the line, slowly slack off the line from the helm or winch so that the line begins to act as a spring, and gradually feed the line out as the boat powers slowly ahead to get fully into the dock.
I use it a bit differently, but I have such an arrangement on my boat. Fiddle blocks with cam cleat are from Gauhauer, but other suppliers are available. Johnson Marine makes a lifeline bracket that slips over the pushpit railing to which you can shackle the fiddle block/cam cleat. I have a block permanently on both sides of my boat.
Last edited by NCC320; 09-05-2011 at 10:34 PM.