7 Hilarious Sailing Disasters You’ll Be Glad Weren’t You

Every sailor’s worst fear? Running aground, sinking, or smashing into another vessel. Unfortunately, these nightmares sometimes become reality. We’ve gathered some jaw-dropping sailing disasters that prove just how fast things can go sideways on the water.

If you’ve spent time watching sailing vlogs, it’s easy to assume the lifestyle is all about turquoise waters, secluded anchorages, chilled drinks at sunset, and the occasional maintenance day. But behind those idyllic scenes lies a world where the unexpected can—and does—happen.

Here’s a roundup of seven intense sailing fails caught on video, featuring everything from grinding against coral reefs and discovering hull damage in the middle of the ocean to playing pinball with other boats in a crowded marina. Painful to watch? Absolutely.

Take Ben and Alie, for example—creators of the Breaking Waves YouTube channel. The duo set off from British Columbia aboard Kiana, their Sceptre 41 sailboat, in 2020. After reaching Mexico and making the big leap across the Pacific, they arrived in French Polynesia, living the dream… until disaster struck.

One night, an unexpected storm rolls in. Anchored close to a reef—common in those parts—they’re suddenly hit with 40-knot winds in total darkness. Fearing their anchor might drag and push them onto the reef, they decide to raise it and get out of there.

But as Ben inspects the windlass, he notices the anchor rode is under serious tension—likely snagged on coral. When they try to power forward to dislodge it, Kiana doesn’t budge. It’s too late—they’re already grounded. Waves and wind slam the hull against the reef.

In desperation, Alie radios the local Coast Guard. Hours later, a rescue boat attempts to free them but fails. Heartbroken, they abandon Kiana and make a tearful dinghy ride to shore. Alie can be heard sobbing in the footage—a raw moment that hits hard.

Thankfully, the story doesn’t end there. In later videos, the couple shares how they managed to recover and repair Kiana. It was a brutal chapter in their journey—but one they survived with grit and a bit of luck.

Taking on Water in the Bahamas Aboard a Small Sailboat

In this gripping sailing episode, Tim and Candice—cruising on Lady K, a Hughes 35—encounter a serious emergency during a short passage from Staniel Cay to Black Point in the Bahamas. Just four miles from their destination, battling 20-knot winds and rough chop in only 15 feet of water, Candice heads below deck and is shocked to find the saloon flooded.

Panic gives way to rapid response. They attempt to activate the bilge pumps—nothing happens. With the water rising, Candice grabs a bucket and starts bailing while Tim shuts all seacocks, hoping to isolate the leak. When the flooding continues, they drop anchor to stabilize the boat and focus fully on damage control.

Realizing they’re in serious trouble, Tim makes a Mayday call on the VHF. Within minutes, a U.S. Coast Guard helicopter is overhead, and a nearby center-console boat arrives to assist.

Following standard emergency procedures, Tim and Candice don life jackets and prepare a ditch bag with passports and essentials. But then they recall something: the through-hull transducers in the bow haven’t been checked. Tim dives into waist-deep water and discovers a 2-inch hole. He manages to plug it—and the leak stops instantly.

The Coast Guard offers to summon a professional pump service, but Tim declines due to the potential cost. Their plan was to continue bailing by hand—until the console boat returns with a high-capacity pump borrowed from a nearby schooner. It’s a lifesaver; what could have taken hours is resolved far more quickly. Disaster averted—just in time.

Chaotic Docking Incident in Greece

This tense boating mishap takes place in Marina Ermioni, a luxury marina in the peaceful town of Ermioni, on Greece’s Peloponnese peninsula.

On a blustery day, a Jeanneau monohull attempts to back into a tight berth between two moored boats. Unfortunately, the skipper misjudges both wind direction and strength. The boat ends up beam-on between the two yachts, smashing repeatedly into them. As the situation escalates, the Jeanneau remains unsupervised, while a family aboard a neighboring catamaran desperately tries to fend it off.

Suddenly, a strong gust shoves the Jeanneau sideways—right into the bowsprit of another nearby vessel. The impact tears into the sprayhood, and the helmsman throws the throttle forward to escape, causing even more chaos.

A second attempt to berth doesn’t go any better. This time, the Jeanneau slams into the catamaran’s bow. The onboard family shouts in panic, fearing injury. The Jeanneau’s gangway snags on the catamaran’s lifelines and stanchions, partly ripping off in the process.

Clearly rattled, everyone looks visibly shaken. The video cuts off with no resolution, leaving viewers wondering whether the Jeanneau ever managed to dock—or wisely chose to anchor and wait for calmer weather.

Near Disaster in the Philippines: Major Mid-Passage Failures

Jason and Nikky Wynn, the adventurous couple behind the popular sailing channel “Gone with the Wynns,” share one of their most nerve-wracking experiences at sea. Sailing aboard Curiosity, their 2023 HH44 hybrid-electric catamaran, the couple is en route to Samal Island in the Philippines, seeking shelter in a typhoon-safe zone.

Things begin going wrong fast. On the first day of the passage, the starboard engine’s belt snaps, taking that engine offline. Later, during a tense night watch, they narrowly avoid a collision with another vessel. To top it off, one of their fridges fails—just what you don’t need in the tropics.

This journey, meant to be a routine leg of their cruising life, turns into a relentless test of endurance, decision-making, and mechanical improvisation. The Wynns share it all—the stress, the near-misses, and the sheer unpredictability of life at sea.

The Worst Was Still Ahead

After a turbulent night spent battling squalls and constantly reefing sails, the couple wakes to a haunting stillness. The sea is littered with debris—remnants of the passing storms—and the wind has all but vanished.

That’s when they notice a foul, chemical odor seeping from the port engine’s exhaust. Curious and concerned, they check the engine compartment, only to be met with noxious fumes. One of the engine batteries is hissing—it’s dangerously overcharged. The culprit? A fouled propeller creating resistance and stressing the charging system.

Keeping their cool, Jason and Nikky contact the HH support team. With their help, Jason carefully swaps out the swollen battery for a spare buffer battery. The workaround holds, allowing them to limp to port—crisis averted, just barely.

Disaster in the Pacific: A Dismasting at Sea

James, skipper of SV Break of Dawn, an Oyster 485, is mid-crossing from French Polynesia to Panama when the unexpected call comes in. The US Coast Guard relays a distress signal from SV Yara, a French sailboat adrift just 60 nautical miles away—dismasted, injured crew, and in serious trouble.

Yara’s crew had attempted to rig a jury mast using their boom, but to no avail. One crew member is injured—his leg wound has turned septic. Out of options and low on hope, they prepare to abandon ship.

When Break of Dawn reaches them, the sailors make the heartbreaking decision to leave their beloved boat behind. They offer a silent prayer of gratitude to the vessel that protected them and climb aboard James’s yacht.

During the journey, they confess they don’t know why the mast failed. It was a calm night—nothing unusual. One loud crack later, the rig was in the sea. Perhaps a structural failure; perhaps an unseen flaw. They’ll never truly know. Yara had been drifting for six days before rescue found her. An incredibly close call.

Flooded and Fading in the Caribbean

Beau and Brandy are cruising the Caribbean with their loyal dog, Oona, aboard their electric-powered 35-foot sailboat, Saoirse. On a routine passage from Puerto Rico to Grenada, their peaceful sail turns terrifying.

After five calm days at sea, Brandy jolts awake to the bilge pump screaming and water flooding in fast. Beau investigates and finds a long crack along the bow. It’s 11 p.m., pitch-black, and they’re still 60 miles from safety.

They shift their tack to raise the damaged section out of the water. Beau attempts a quick fix using high-strength marine sealant, but the water keeps rising. Resorting to manual bilge pumps, the couple fights to keep Saoirse afloat. By dawn, the saloon floor is nearly knee-deep in seawater, and panic begins to set in.

Just in time, two Grenadian fishermen respond to their VHF distress call. They bring over two-part epoxy, instructing the pair on how to apply it from both sides of the hull. It works. They limp into Grenada and later haul out to properly repair the damage. Another close brush with disaster, ending in relief.

Ghost Ship in the Atlantic

Matt Rutherford, head of the nonprofit Ocean Research Project, is leading a scientific expedition 800 miles from Bermuda when his crew spots a vessel behaving strangely—a Swan 48 adrift, engine silent, sails in disarray, and no one in sight.

Curious—and wary—Matt boards the sailboat. The interior is chaotic, as if the crew fled in a rush. There’s no one aboard, and the engine is completely dead. With no signs of life or a clue as to what happened, the ORP team decides to tow the derelict boat to Bermuda.

But towing a 48-foot sailboat with a 42-foot research vessel is no easy feat. After two grueling days, their own engine fails. They switch to sailing while towing, but strong winds cause the towline to dangerously wrap around the rudder. Fearing permanent damage, they cut the line.

The mystery yacht drifts away once more, and soon after, the wind vanishes. Matt and his crew are stuck—becalmed in the middle of the ocean for 23 long days before they finally reach Bermuda.

As for the Swan 48? Its fate remains unknown, still lost in the vast Atlantic. Perhaps one day, someone else will find it.