Best Sailing Movies to Watch on Long Winter Nights
Summer is easy.
You go sailing.
Winter is when you start watching other people go sailing instead.
I have always preferred winter anyway. When we lived aboard Milda, rainy days on the boat were some of my favourites: the heater on, coffee in the saloon, rain tapping on the hatch above us.
Add a good sailing movie and, really, there are worse ways to spend a dark evening.
So this is not a giant list of every film that happens to contain a boat. These are some of the best sailing movies for people who actually like the sea — racing, survival, adventure, ocean passages and the occasional reminder that sailing can go very, very wrong.
Streaming availability changes constantly and depends on where you live, so I have deliberately left that part out.
Blanket ready?
1. All Is Lost — For the Sailor Who Will Spend the Entire Film Saying “Why Did He Do That?”
Robert Redford.
A yacht.
The Indian Ocean.
And almost no dialogue.
All Is Lost follows a solo sailor whose 39-foot yacht is damaged after colliding with a floating shipping container. From there, the problems keep coming: damaged communications, bad weather, dwindling supplies and increasingly limited options.
If you sail, watching this film becomes slightly interactive.
You will probably find yourself mentally repairing the boat, questioning decisions and occasionally talking to the television.
Which, to be fair, is part of the fun.
Watch it if: you like survival stories and very quiet tension.
2. Maiden — For Anyone Who Loves Ocean Racing
This would be high on my list.
Maiden tells the true story of Tracy Edwards and the first all-female crew to compete in the Whitbread Round the World Race in 1989–90.
They were told they would not find funding, would not be strong enough and probably would not even reach the start line.
They reached it.
Then they raced around the world.
The documentary uses archive footage from the actual campaign, and the story goes far beyond sailing. It is about racing, teamwork, determination and having a lot of people confidently tell you that you cannot do something.
Those stories rarely age badly.
Watch it if: you love offshore racing, real sailing footage and underdogs.
If round-the-world racing is your thing, you might also like our guide to the Top 10 Famous Sailing Races in the World.
3. Wind — For Old-School Yacht Racing
If Maiden gives you real offshore racing, Wind gives you Hollywood yacht racing.
Released in 1992, the film centres around the America’s Cup and a sailor trying to win the trophy back after losing it to the Australians.
Is it subtle cinema?
Not particularly.
Does it have beautiful racing boats, competitive sailors, big sails and enough 1990s drama to keep a winter evening occupied?
Absolutely.
And compared with many films that treat a sailboat as merely attractive scenery, Wind actually puts sailing at the centre of the story.
Watch it if: you want racing, boats and nostalgia rather than psychological suffering in the Southern Ocean.
We have enough of that coming later.
4. True Spirit — For Something More Hopeful
Sometimes you do not want everyone to be shipwrecked.
True Spirit is based on the story of Australian sailor Jessica Watson, who set out at 16 to sail solo, non-stop and unassisted around the world.
Her voyage lasted 210 days and took her across some of the world’s most challenging stretches of ocean.
The movie is more family-friendly and inspirational than some of the darker films on this list, so this is a good choice if you want sailing without spending the evening wondering why humans ever decided to leave land.
Watch it if: you want a lighter true-story film, or something to watch with older kids.
5. Adrift — For Sailing, Survival and a Love Story
Adrift begins as a sailing adventure and romance.
Then the weather has other plans.
Based on the real story of Tami Oldham, the film follows a couple sailing across the Pacific when they encounter a catastrophic hurricane. Their yacht is badly damaged and survival becomes the entire job.
There is plenty here that will feel familiar to sailors: damaged equipment, limited resources, navigation problems and the uncomfortable reality that at sea you sometimes have to solve the problem with whatever is still working.
It is also considerably more emotional than All Is Lost.
Robert Redford does not provide much romance.
Watch it if: you want survival mixed with a human story.
6. Deep Water — For the Dark Side of the Golden Globe Race
Now we arrive at Donald Crowhurst.
And things become considerably less cosy.
Deep Water is a documentary about Crowhurst’s attempt to compete in the original 1968 Sunday Times Golden Globe Race — the first solo, non-stop round-the-world sailing race.
It uses material including Crowhurst’s own film footage, logs and audio recordings, which makes the story particularly haunting as the pressure and isolation begin to take their toll.
This is not really a film about whether someone can sail around the world.
It is about what can happen when ambition, fear, isolation and expectations all meet in the middle of an ocean.
Definitely not the cheerful option.
Definitely worth watching.
Watch it if: sailing history and the psychological side of solo ocean sailing interest you.
We wrote much more about Crowhurst, Robin Knox-Johnston, Bernard Moitessier and the race itself in The Golden Globe Race: Sailing Like It Is 1968.
7. White Squall — For Tall Ships and Crew Dynamics
This one takes us away from solo sailors.
White Squall follows a group of teenage boys aboard a sail-training ship under the command of a demanding skipper. What begins as an adventure and coming-of-age story eventually becomes something much more serious.
It is less about yacht ownership and more about seamanship, discipline, crew relationships and what happens when conditions at sea suddenly stop being forgiving.
And sometimes it is nice to watch a sailing film where there are actually enough people aboard to help.
Watch it if: you like tall ships, crew stories and classic adventure films.
8. Master and Commander — Not a Yacht Movie, But I’m Including It Anyway
No, this is not cruising.
No, nobody is discussing lithium batteries or marina fees.
And the boat is somewhat larger than the usual Sailoscope reader's.
But Master and Commander: The Far Side of the World is simply too good a sea film to leave off the list.
Set during the Napoleonic Wars, it follows Captain Jack Aubrey and HMS Surprise in pursuit of an enemy ship across two oceans. The film received ten Academy Award nominations, including Best Picture.
What makes it enjoyable for sailors is the atmosphere: sails, weather, navigation, crew, repairs, watches and the feeling of being aboard a working sailing vessel rather than simply looking at one from shore.
Also, occasionally it is healthy to watch somebody else deal with much more complicated rigging than yours.
Watch it if: you want a proper big-screen sea adventure.
Which of These Best Sailing Movies Should You Start With?
That depends on the evening.
Want real sailing history? Maiden.
Want survival? All Is Lost.
Want something uplifting? True Spirit.
Want yacht racing? Wind.
Want something dark? Deep Water.
Want a proper sea epic? Master and Commander.
Personally, I think winter and boats work very well together.
Summer sailing gets the photographs: blue water, bare feet, cold drinks in the cockpit.
Winter has the heater, rain on deck, an almost-empty marina and nowhere particularly urgent to be.
Sometimes that is just as good.
Especially when the sailing is happening on the television and somebody else has to deal with the storm.
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