There is a very good cruising documentary called "Ice Blink". Very well done, and at times poignant. There is a free preview of the DVD on our site (yes, you can buy it there, or on thesailingchannel.com site, or at iceblink.com - but at least you can see a bit of it to know if you would want to order it):
Latitudes and Attitudes Television
Click on "Other Sailing Videos" in the upper right, and then click on the "Ice Blink" DVD preview. Then click on "Play Part 1" in the lower right. I know, it's a pain to navigate our TV site. I'm trying to get it fixed to be a lot easier and more intuitive.
The preview was produced by Tory Salvia at thesailingchannel.com. He did a wonderful job of capturing the essence of the film. After watching it, my wife became even more interested in cruising.
I also like the Shards DVDs, and "Project BlueSphere" by Alex Dorsey. "Sail Vicarious" is fun to watch, with high end amateur video work.