Great morning of sailing with Melanie. I picked #4 because it seemed like it would be a nice upwind docking later. (Was very wrong. Ack.) We set out and had a great bit of sailing out past Ft McHenry (pausing to heave to and reef at the turning basin), about halfway to the bridge, maybe a little less, before turning back. Got back in record speed on a solid beam reach the whole time so instead of docking we went back up to the turning basin and did a couple POB's for Melanie to practice and she did fantastic. Then we went back to DSC to dock and it was a shifty but pretty strong upwind/crosswind situation. I thought I might time it for an upwind but then couldn't, then I tried getting close and dropping the sail which was a mistake because I just blew over towards the pilings so raised the jib fast and headed to B dock and stopped there to raise the main and try again. Fucking screwed it up AGAIN, ended up at b dock again, was really feeling stupid and worried at this point. Went back and decided I couldn't drop the main and still get into the skip, but also didn't see a way to truly depower. Ended up going as slow as I could sheeted in on a beam and blew the main using the spaghetti to guide in hit that was still pretty hot and I'm lucky Melanie is very competent and fit enough to stop us. I have been trying to figure out what a better solution would have been. I think the correct thing would maybe have been to sail into the area between the fingers and turn into the wind, pause, drop sail, turn back or maybe complete a pivot, and drift sideways into the slip. But I was terrified of coming into that space so fast and having nowhere to go. Would the boat have stopped before hitting #8 or #12? I don't feel confident that it would. I really need to get some advice about this. But other than that bit at the end it was an amazing morning.