Armchair Travel: 10 Films about Sailing

I’ve put together a list of my favourite sailing movies, including Hollywood blockbusters, all-time classic films, and inspiring documentaries. 

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In my previous edition of Armchair Travel, focused on Ocean films, I struggled narrow it down to just 10 of my favourites, and not to fill up the list with sailing movies filled with beautiful boats.  So I split the two, and decide to offer you up a second helping.

I’ve put together a list of the best sailing movies I’ve seen, a mix of modern and classic, drama and documentary film.  Tragedy and terrifying ordeals, unimaginable tales of survival, tempestuous adventures, and inspiring journeys of discovery all feature in my selection of sea-soaked cinema.  Perfect for a dry night in on the sofa.

  • Swallows and Amazons (1974)

A classic film for a rainy Sunday afternoon.  Four children (the Swallows) spend an idyllic summer learning to sail in the English Lake District, encountering ruthless pirates (the Amazons), before setting aside their quarrels to take on Captain Flint.  The film is all about children’s rivalries and relationships. Swallows and Amazons forever!

  • Age of Sail (2018)

A beautifully animated short film that captures the end of an era, as the old skipper of a traditional Bristol pilot cutter contemplates his place in a world of steamships.  The whole thing (12 minutes) is available to watch on youtube.

  • Deep Water (2006)

An excellent documentary telling the true story of the first-ever solo, non-stop, round the world sailing race in 1968. The film focuses on the tragic story of Donald Crowhurst and gives a real insight into how extreme solitude can affect mental state.

  • Adrift (2006)

A nautical horror that takes its power from the simplicity of the plot.  A group of friends on an offshore sailing trip decide to take a dip in the ocean, leaving only a young baby aboard.  But who remembered to rig the boarding ladder?

  • White Squall (1996)

Based on the true story of the school ship Albatross, which sank in the early 1960s, with a trainee crew of American teenagers.  The voyage of a lifetime, learning about teamwork and discipline, becomes a harrowing battle for survival after encountering freak weather conditions.

  • Captains Courageous (1937)

A nautical film classic based on the 1897 novel by Rudyard Kipling.  A spoiled rich boy falls overboard from a steamship, and is recovered by a Portuguese fishing vessel.  To earn his keep onboard, he must join the crew in their work, and soon learns the lesson of hard graft in this touching film.

  • Dead Calm (1989)

If watching White Squall (awful weather) and Adrift (going overboard) haven’t scared you enough, this chilling thriller will finish you off. A grieving couple set sail on the trip of their lifetime. All is going well until they rescue a lost sailor who is drifting at sea…

  • Maiden (2019)

British sailor Tracey Edwards made history by skippering the first all-female crew in the Whitbread Round the World yacht race in 1989.  This documentary dives deeply into the challenge of the competition on the open ocean, and the sea of misogyny faced by Edwards and the Maiden crew from other competitors and the press.

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Sailing west into the setting sun on Atyla.
  • Master and Commander: The Far Side of the World (2003)

Russell Crowe makes a fine Captain Jack Aubrey in this period action film adapted from several Patrick O’Brien novels.  Expect a pretty accurate depiction of a ship during the Napoleonic Wars, and some superb sailing sequences as Captain Jack Aubrey pushes his crew and ship to the limit whilst in pursuit of a French warship.

  • Captain Ron (1992)

A light-hearted comedy adventure film about a family that inherits a yacht and decide to set off on an adventure with the unlikely Captain Ron. I will die on this hill: this is one of the greatest films about sailing ever made, and that Kurt Russell is a brilliant actor (see The Thing, Big Trouble in Little China, Escape from New York, Tango and Cash, and the rest for more confirmation).

Which is your favourite sailing film?  Do you have any recommendations?
I’d love to hear from you; let me know what you think in the comments.
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Author: vickyinglis

These Vagabond Shoes are longing to stray.

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