Why do they insist you dock stern in? I think you should dock whatever way is the easiest and safest. In my boat (and my understanding is most sailboats are similar) I have very little control moving slowly in reverse so I park her bow-in.
I'm still trying to understand the insistence some people have with backing into the slip ... I've seen several people in my marina this year try again and again and again to back in, failing and getting damn close to running into something when it seems to me they could just go bow-first and save a lot of trouble.
Thanks for all the replies.
The dock I use is the Mt Sinai marina on Long Island, operated by Brookhaven Town. Each slip has outer pilings. Most slip holders (me included) have rigged lines from the dock to the pilings, which have spliced eyes to act as spring lines. The piling end of the lines are attached to rings which slide up and down on poles with the tides. These rings are shared by neighboring slips. There have been a number of incidents of boat damage due to the ring getting snagged on the bottom of the pole and not coming up with the rising tide. My previous boat had a winch ripped off the coaming during such an incident. The harbormaster claims that boats which dock stern to have never been damaged like this due to the bow being a foot or two higher than the stern. So, even at low tide, the ring doesn't get to drop that low. That is the basis for their "encouragement."
It is certainly easier for me and my occasional passengers to get on and off the boat from the stern. But that is another matter.
My approach starts out in the channel. I get some RPMs up in reverse. During this process the boat behaves much like a reluctant cow with the bull approaching rapidly from the rear -- the stern moves from side to side until finally I get some way and it actually begins to move backward. by the time I am in the fairway this awkward stage has passed and I have mastery of the vessel. Until I turn in a stiff cross breeze and the wind grabs the bow, and the mastery quickly disappears. With my boat this does not occur until the cross wind is approaching 20 kts.
I will try some of the remedies proposed, but the easiest is to come in bow first when the wind requires it.