C320FIGA001.jpg picture by pboatppp - Photobucket
Not sure how to post the picture directly, but this link should show the situation. The slip dimensions are approximately to scale, so you can see it is tight.
The issue is on the downwind side towards the finger pier. Contact will be made with the outer piling on the finger pier side, i.e. downwind. It is here that I am concerned. You can see that I cannot put fenders or fender board over before I enter the slip. Otherwise, they are going to trip up the boat and cause it to swing towards the adjacent slip. It is the up and down wave motion on this piling that I am concerned primarily about. However, getting further into the slip once I get the boat off the piling may be done in several ways. Depending on the exact direction of the wind and which lines I work with, I generally can stay off the windward piling.
Hope this clarifies the situation. I really would like to work this one out because our wind is primarily from the SW and I (and all the people at this marina) miss out on some good sailing conditions. If the wind is from the N or E, then we don't have a problem as we are sheltered from the shore. W and especially SW, which is towards open water, give a problem.
It's a package deal, a nice marina, clubhouse/pool, great view, nice townhome, and wind that sometimes gives problems docking. So I have to figure out how to do it without messing up the boat.
If I have crew, it'll go easier, but we still are going to get blown down on that downwind outer piling no matter what if the wind is high. Most of the time I singlehand, or am sailing with people not well versed in sailing and docking techniques.