One really bad one is the final scene from "The Tourist".
Jonny Depp and Angelina Jolie set sail from Venice in a rather pretty yacht. The main is hoisted and sets with a pop but the boat does not heel, the boom does not move nor does the headding change...
It did look very pretty.
There's an old '80's movie called "Wind".
Fictional Americas Cup campaign.
The movie is a cheesy, chick flic, but the sailing sequences, and there are quite a few, are really good.
Sam