A few sailing movies you might want to check out...

[capnjohn]

"Master and Commander" - Russell Crowe

"Dead Calm" - Nicole Kidman (before she met that Cruise guy...)

"Waterworld" - Kevin Costner (yes, I know it was terrible, but it has great sailing footage!)

"Mutiny on the Bounty" - B&W original and remake with Mel Gibson as Capt.

Someone else already mentioned it, but "Wind" has really great footage also.

Enjoy!