Another movie that I've only seen twice is Billy Budd
Filmed in 1962, from the book of the same name written by Herman Melville, Directed by Peter Ustinov depicting a dire situation on a British Navy frigate in 1797. The cinematography is amazing with very real footage of the ship sailing and crew work.
The most amazing historic sailing documentary ever filmed was by Irving Johnson in 1929 as he sailed on the Brig PEKING, entitled "Around the Horn".
The Peking is moored at the South Street Seaport & Museum where a small theater shows this film daily.
It can be purchased also in DVD.
I recently saw Open Water 2 - Adrift. It was based on the true events of some friends out for a sail, they jump in the water to take a swim but no one put the ladder down...this movie went straight to video. It's any sailors worst nightmare-