John Rousmaniere has produced some.
Those are pretty good videos. He covers a range of topics, including planning a weekend cruise with navigation tips.
The problem I have found is that I couldn't find any that were made less than 20 years ago, and I have looked. Granted, sailing hasn't changed much and most of us are sailing on boats that were old when the videos were made, but the production values are pretty damn bad. I always feel like Magnum PI is going to pop out of the cabin while watching.
It would be great to see some new vids out there that appeal to a younger crowd and not cement the perception that it is an old fart's sport.
That said, "Penny Whiting's Learn to Sail" is pretty good and I learned most of what I know of docking from "Captain Ron".