Woody Allen's new movie, "Cassandra's Dream" has some decent sailing scenes in it (the title, "Cassandra's Dream", is the name of a sailboat in the movie). "Islands In The Stream" with George C. Scott can also pass as being very nautical.
Allow ole'Capt Dave to add to the list a wonderful movie called "The Dove" directed by Gregory Peck about Robin Lee Grahams circumnavigation and the classic "Captains Courageous" with Freddy Bartholomew, John Barrymore, and Spencer Tracey...there's some absolute classic b/w film of real sailboats in that flick. Both are a must for every sailboaters collection. Extra note. check out Zac Sunderlands web site.....wanting to be the youngest person to circumnavigate....beating Grahams age by a year.....16 years old.....so long for now...
Not quite about sailing, The Guardian is a great movie about USCG rescue swimmers. Starring Kevin Costner & Ashton Kutcher, 2006. It has some really exciting action scenes of a sailor's worst nightmare!
I just saw one a few nights ago called, "Kidknapped in Paradise" if I'm not mistaken. I don't know if I would classify it as one of the best movies about sailing though, but there are'nt many around. But dead calm was pretty good. Another one that comes to mind is, "Water World" with Kevin Costner. Maybe its because of all these movies about sailing that makes me think I need to be well armed if I'm going to own a boat. Are there any movies about sailing that doesn't involve kidnapping, robery and murder? I'm having trouble thinking of one.
Besides the aforementioned "Wind," there's also "Failure to Launch," with Matthew McConnaughey and Sarah Jessica Parker. As I recall, he's a yacht broker, and there are a few choice scenes involving the two of them aboard a gorgeous sailboat. No kidnapping, no robbery, no murder.
When I was in college, Captain Johnson of the Brigantine 'Yankee' (National Geographics fame) came and showed 3 hours of 16mm film of a circumnavigation. He narrated the movie giving me not a desire to sail but a lust to sail. If that film were made available on DVD, I'm sure that all of you would buy it.
I also give high votes for 'Wind' and 'Master and Commander'. I only wish that in 'Master and Commander' they had followed the book. I guess the book was not sufficiently Hollywood.
I'll throw in 'Knife in the Water'. It was the film that gave Roman Polanski (he directed 'The Pianist) international recognition. I realize that it would be a 'reader' for most of you, but it does give some beautiful sailing scenes.