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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Armchair Travel: 10 Books about Sailing Adventures

I’ve compiled a selection of my favourite books about sailing adventures, both real and imagined, idyllic and horrific. 

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This instalment of the Armchair Travel series is brought to you with a healthy dose of vitamin sea.  Like travelling (and sailing), these books could bring you complete escapism, teach you new skills, and ideas or throw you in at the deep end.  So hoist the mainsail and catch the wind, and head off into the sunset with ten of my favourite books about sailing adventures…

  • Sailing Alone Around the World – Captain Joshua Slocum

The single-handed circumnavigation of the globe Slocum made on his sloop Spray was the first time such a voyage had been made.  Sailing more than 46,000 nautical miles, crossing the Atlantic three times and the Pacific once, long before radar and satellite, the understated and direct writing isn’t overwhelmed by the extraordinariness of the achievement.

  • The Kon Tiki Expedition – Thor Heyerdahl

This is my most favourite book ever, and I first read it when I was around 10 years old.  More about the adventure than sailing, this is the account of Thor Heyerdahl and his companions taking a balsa raft more than 4000 miles across the Pacific from Peru to the Tuamoto archipelago.  I was really interested in the way the crew handled the challenges, excitement, danger, and boredom of the voyage.

I loved this book, but I think it will be a challenge to explain why.  The story of the seafarers of Marstal, Denmark, from the golden age of sail to the end of the Second World War, from Scandinavia to North America to the islands of the South Pacific.  Despite the epic scope of the book, the pacing is tight, and twists and turns in the plot unexpected. The writing is beautiful and thoughtful, and the book is rich in historic detail, but it is so much more than the sum of its parts.

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A classic children’s book set in the English Lake District in the 1920s, this is the tale of an idyllic summer of adventures, friendship, and imagination for the children of two families and their sailing dinghies, Swallow, and Amazon.  The “ruthless pirate” Nancy Blackett was my childhood hero, and after watching the film so many times, I can’t run through a meadow without throwing in a tack.

Using medieval texts as a guide, experimental archaeologist, adventurer and writer Severin constructed an ox-hide curragh and traces what may have been the first European landfall in North America, around 500 years before Norse settlements and a thousand years before Columbus.  Weathering storms and treacherous conditions, close encounters with marine life, and living in the most basic of conditions.  A truly remarkable undertaking, and an insight into medieval boatbuilding technology that is little heard about.

In 1938, Newby, then aged 18, quit his job at an advertising firm, and signed-on as crew on the windjammer Moshulu, to sail from Ireland to Australia, round the Cape of Good Hope, and back again via Cape Horn. The Great Grain Race of 1939 was the last, with the outbreak of war later in the year. Life at sea was hard, physically and mentally, and tensions grow with the weather. Bawdy anecdotes of brawls and benders are balanced out with lush, lyrical descriptions of wind, waves and wildlife. The book helpfully includes a sail plan and rigging diagram so you can keep track of topgallants, flying jibs and spankers.

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Writer and broadcaster Heiney’s son Nicholas, a keen sailor and poet, took his own life aged 23 after years of living with depression.  Together with his wife, journalist and sailor Libby Purves, Heiney pays tribute to Nicholas, and aims to connect with happier memories, by setting out for Cape Horn, considered the Everest of sailing.  A powerful and moving account of processing grief, beautifully written and thought-provoking.

For centuries seafaring navigators could fix their latitude accurately with a sextant, but the calculation of longitude was far more prone to error.  The British Admiralty established a prize for the first person to develop a technique, thus ensuring their continued naval superiority, leading to John Harrison’s forty-year quest to build the most reliable chronometer of the time.  A classic of the history of science.

A fictionalised life of Captain Robert FitzRoy of the Royal Navy, commander of HMS Beagle, and pioneer of meteorology, this superbly written book is captivating from the start, and filled with historic details. It traces FitzRoy’s voyages to chart the coasts of South America and introduces a young Charles Darwin, trainee cleric and keen geologist, engaged as a gentleman companion to the captain on the second voyage. The two men discuss, debate, observe, and speculate, on a range of themes, until profound differences in their beliefs eventually drive a wedge through their friendship, exacerbated by their receptions by society on their return.

More people have walked on the moon than have made a successful solo westabout circumnavigation, against prevailing winds and currents, and in 2006 Dee Caffari was the first woman to do so.  Stepping out of the comfort of a secure job, to face physical hardship, sleep deprivation, and the unpredictability of the weather, this is an inspiring account of her adventure.

Have you enjoyed any of these books?
Which salty adventures would you recommend for me?
I’d love to hear from you; let me know what you think in the comments.
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