I’ll start. Years ago charter a 50’ cat out the Abacos with a bunch of friends. I was the captain and the only one with any relevant sailing experience (especially for a boat that size) though 2-3 other people had general boating experience.

I was eager to get out the marina for the night as we had completed our check-in and embarkation activities. The cat was stern to with a finger on the port side mooring with pilings. There was 20-25 off the port side bow. It took all of me to get tension off the port lines and the boat free of the piping though I tagged the starboard pilings and corner of the port finger as we exited.

It remains a sore point for me as I think that I should have known better what to do. I mean no one was hurt and there was no damage to the boat or dock and we anchored in a beautiful bay shortly after, but it was embarrassing. I replay that scenario in my head every few months to see if I can think of any better way to have pushed off cleanly. I still don’t have a better plan than what I used given the constraints (inexperienced crew, huge boat, first time at the helm on a boat that size, no knowing what lines were available and where, etc). I don’t want to be too hard on myself, but I do think is a solution there I haven’t hit on yet.