Having your oldest son sail a twilight race with you.
I was embarrassed that the wind was not cooperative: it diminished from 17 knots at the start to 10. I was disappointed in my own attention to detail at the leeward mark's sail handling. And, I was enraged that a J-105 flagrantly port-tacked us at the finish line. But, other than that, this was a high point in the summer. Definitely!