My worst ride was being out with some kids in a thunderstorm. I'd just come out of a small cove when the skys openned up. I only had 2-3 miles in a straight line to get back to the dock but all the wussies in thier bigger boats decided the conditions justified their cutting me off from all directions causing me to stuff my bow a couple times.
Two of the boys were in front thinking it was fun until I moved back while the third was in the rear with me looking towards the stern from a lounge seat. It was almost funny when he looked down at his dangling feet and saw 3 inches of water sloshing around! Fortunatly I'd sprung the few extra bucks for a higher capacity pump,it it was cleared in a couple minutes. I turned around and went to back to that cove where we circled with some other small craft for about 45 minutes until things calmed down.
If it was just myself the situation would not have botherred me but I really would not have wanted a head-line "Man kills 3 kids taking boat into heavy water." After we got back I learned one of the mothers had been anxious but the other two having been around boats settled her down by telling her we'd probably tied up somewhere to ride it out.
My second worst ride was the year my night-vision mostly went away. There are a lot of small islands on my favorite lake and it's easy to confuse them. Things did not look right to me at one point and I cut to idling speed and went to a lighted (numberred for ID) bouy and found I was about a mile away from where I thought I was and had just passed through a small rock field. I gave up night riding until I got a chart-plotter that included that lake.