I'll toss in second votes for "Wind" and "Master and Commander". Both are outstanding.
And, while not a sailing movie, I was totally drooling in my lap watching that lovely Spirit Yacht that James Bond and Vespa sailed into Venice Harbor in "Casino Royale".
Hollywood really needs to create more sailing films and television programming. It's sad that I can watch Mixed Martial Arts cage matches or bullriding day or night, but very rarely do I see televised sailing events. I'm betting there are more sailors out there than there are rodeo riders!
I'm gonna have to add a 3rd for "Wind" ...yeah..some of the storyline is definately hollywood ...but the meat and potatoes of the movie is the swift depiction of racing ....all that is good ..and all that isnt so good ....still...if you dont like that ...you HAVE to enjoy the Aussie boats flying at breakneck speeds ...truly exhilerating to watch! I'll give a good second to Master & Commander as well ..they definately made the movie believable and enjoyable in its own rite.
Here's a more obscure European release that I really loved: THE WEIGHT OF WATER with Sean Penn. "The story of a troubled couple spending a tense working vacation on a sailboat with the husband's brother and his enticing girlfriend, and the story of a century-old murder on the New England island where they're anchored"