Join Date: Mar 2008
Location: Buzzards Bay
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A bit obscure, but a classic 80's John Cusack movie has a bit of sailing... Hot Pursuit.
Also Summer Rental with John Candy has a little.
How about Dead Calm? Another obscure late 80's, movie with Sam Niell, Nicole Kidman and Billy Zane. Actually I think this whole movie takes place on a sailboat. I don't think there is any land in the whole movie. That's kind of rare.
Lastly, Perfect Storm. It doesn't have much sailing, but what little sailing it does have is pretty awesome to watch. And there is just a ton of great ocean footage (whether real or fake...)