When I was 16 I had an old Hobie 16 that I would single-hand around the bottom of Tampa Bay and that part of the Gulf of Mexico
One day my sailing mentor, Bo, was on his Prindle 18-2 with me following along in my Hobie. We were sailing out of the ICW
to go around the north end of Anna Maria Island and stop at one of our favorite restaurants.
It was almost a dead calm, but of the two piers that stick out from the north end of the Island, the west-most had a flag flying which was standing straight out. I watch as Bo goes past, trapezes off the side and flies the hull
nice and high for all the people fishing
off the end of the pier.
I figured I could do better...
...so I sail closer to the pier, just far enough that I won't tangle their fishing
lines. Instead of trapezing I just hike out, and let the wind
push the boat over. Too late I realize that I'm too close to the pier to round up, and not being on the trapeze I don't have the leverage to hold her down. Even with the sails
dumped, she still goes over.
I was close enough to the pier to hear a collective "awww..." from the crowd as I did my swim of shame.