A white motorboat precariously balanced on the bed of a pickup truck at an intersection.
via Canva

Some boating tales seem to truly be written out in some kind of fiberglass and facepalms. This roundup in particular is aimed squarely at the “everyone’s okay” end of the spectrum. Pride dents, the property damage, and then the teachable moments on the water. It’s really all a whole lot going on, and the fails don’t seem to disappoint.

1. Wasn’t the other way around?

A white pickup truck is partially submerged in water at a boat ramp while attached to a trailer with a boat. A man stands nearby holding a rope, and other boats are docked in the background.
diamondclub / via reddit.com

2. That’s an interesting way to sail a boat

A person wearing a red life jacket sits on top of a capsized small sailboat in a muddy river near a grassy bank, with open fields and a power line visible in the background.
sailing / via reddit.com

3. Pretending to be a submarine?

A sailboat is submerged underwater next to a wooden dock, with only the mast and some parts visible above the surface. Caution tape and a barrier line are set up around the area. Trees are visible in the background.
submechanophobia / via reddit.com

4. What could go wrong with overloading a boat

A group of people stand closely together on a small boat in open water under a bright sky. The water appears calm, and the scene is slightly blurry.
whatcouldgowrong / via reddit.com

5. Another overload that went very wrong

A large houseboat is tilted and partially sinking near the shore of a lake; a small group of people in a boat is nearby, and trees are visible in the background.
mildandfire / via reddit.com

6. What are the odds of a boat crushing into a truck?

A large white boat has fallen off a trailer and is tilted onto a road at an intersection, partially blocking traffic. Vehicles are stopped nearby and the traffic lights are red. Trees and utility poles are in the background.
jj2478 / via reddit.com

7. Breaks stopped working at the wrong time

A large cruise ship is docked very close to a pier, towering over nearby people and vehicles. The ship's bow is prominently visible, and the scene appears to be busy with people walking around.
megalophobia / via reddit.com

8. The famous “keel breacker”

Several sailboats and small boats rest on a muddy shore at low tide, tilted and grounded, with grassy land and rows of more boats in the background under a cloudy sky.
sailing / via reddit.com

9. A broach and an almost collision

A sailboat leans sharply to the side in choppy water, its sails tangled and flapping, while crew members work on deck. The photo is taken from another nearby sailboat. The sky is partly cloudy.
sailing / via reddit.com

10. The world economy lost 1 billion with this boating accident

A large container ship labeled "Evergreen" is stuck diagonally across the Suez Canal, blocking passageway; tugboats and equipment are seen attempting to dislodge the vessel.
wallstreetsilver / via reddit.com

11. Floating hotel goes wrong

A large white boat is tilting heavily to one side as it begins to sink into the ocean, with turbulent water surrounding it and a cloudy sky overhead.
nottheonion / via reddit.com

12. Next time you think rope isn’t a problem, think twice

Underwater view of a boat's anchor chain extending from the hull to a metal anchor resting on the sandy ocean floor, with clear blue water surrounding the scene.
joshpost / via youtube.com

13. He missed his docking lessons

A yacht crashes into several docked boats at a marina, causing visible damage and splashing water; other yachts and waterfront buildings are seen in the background.
thatlookedexpensive / via reddit.com

14. Looks like it fainted

A large ship is heavily tilted to one side at a dock, supported by a blue crane. A person in a yellow vest stands nearby on an empty street, with buildings and traffic cones visible along the road.
wonder_aj / via reddit.com

15. “I think this spot is great”

A boat is stranded on top of large rocks near the water at night, with two people nearby; one stands by the boat while the other sits on the rocks. The scene is dimly lit.
boating / via reddit.com

Explore more humorous content:

If docks could gossip, these boating fails would be their favorite stories. For more grin-inducing scrolls, try these 20 Truck Fails That Are So Bad They Left a Dirty Mark in the History Books, or these 15 Photos of Tunnels That are Borderline Concerning. You can also enjoy these 20 Bumper Stickers That Tried to Lighten Things Up.

Meet the Writer

Matt has spent over the last 8 years as both a writer and editor, working in Seattle and Brooklyn, where he is now based. He loves escaping the tirelessly fast pace of the “Mad Apple” that is NYC by taking walks and runs through parks where he’s able to catch up on the latest tea about society from the city’s ever chatty, always hungry, occasionally maniacal, pigeons. They always have a lot to say. When he’s not taking his urban nature strolls, or dutifully combing the deepest rabbit holes of the internet to find the content that’s worth sinking your mind’s teeth into, he’s likely holed up at a dark-lit dive bar with a new book and/or some friends, or just as easily he could be on the hunt for the next addition to his steadily growing plant family.

These days Matt’s caught up in trying to provide folks as many vivid glimpses into the days long since passed as he can, through fun and engaging collections of hand-picked vintage photos.