I've used Tactical Sailing Solutions (TSS- for short) for a couple of years now, to make situational diagrams for protests. My version was 2.3, and in those years I've periodically looked for updates to the program, without any success. Henri Peronneau, one of the people who created this program, now has a small website. Finally I can download a newer version! This v 2.5B has the now, among other things, the possibility to save as an animated picture (GIF). If you click on the picture the boats start to move. I've used the second protest from Keeping Clear blog to make the animation and it looks great!
If your interested in TSS go to http://tss.peronneau.net/. It's shareware so you can try it out for 30 days, before you need to register.