What is the most idiotic mistake you have made on a boat?

I enlisted an old mate as crew for a race along the coast to a popular summer anchorage. My old mate is not silly and had been sailing with me before but really is not a natural sailor.
on arriving at destination anchorage respectably in the middle of the racing fleet, we found the anchorage also full of other sail and mobos.
I requested my mate to keep the boat head to wind while i lowered and stowed the main in the brisk breeze, but his head was turned, literally, by gawking at some of the floating gin palaces and he turned the boat across the wind just as i had the main down and first sail ties on.
I am sure there are many small minded people who were there that day that still get a chuckle from the memory of seeing the boom as it swung out over the water with me clinging on to it and yelling at my old mate to "head to wind for chrissake!"
All in all I have to say a good tiller pilot is a more reliable help than an old non-sailor mate!
Not such good company in the evenings though.:)
 
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After a fraught sail in my trailer sailer against the wind and tide that had me going backwards, I motored to the slip and ran it aground. The chop was banging the boat about so I thought I'd be wise to retrieve it on the trailer at the earliest possible convenience. Running back to the car I hopped in and raced back to the slip, noting that the trailer seems a bit sluggish even for the Land Rover Discovery. Got to the slip to find I'd forgotten to take off the wheel clamp from the trailer. Said clamp was trapped under the wheel arch. I had to remove the wheel to get it off. Meanwhile, my poor boat....

The marina fuel dock is adjacent to the yacht lift gantry. I thought I'd play clever by reversing against a spring to point the bows clear and then blasting off into clear water. I was just sorting the spring when I looked up and noticed I was actually heading for the gantry. The fuel guy gave a warning shout at the same time and I just had time to put the tiller hard over to clear it by about 1 metre. I didn't dare look back at the bystanders! Always make sure you're clear before messing with ropes!
 
To sell my previous yacht for a very good price, and instead of walking away with the money, to buy my current boat :-)
 
Tried to leave pontoon with shore power attached.[16a plugs are surprisingly strong]
Spent at least an hour on Queenbourgh moorings trying to get the engine to start before realising I hadn't returned the stop lever.
I think there are others but they have been expunged from memory.

Martin
 
car park

Anchored a westerly on Blakeney carpark at high tide. Reversed back and forwards to try to dig anchor into asphalt, oldchart said scrubbing sands !had I got dug in then I would have been in the middle of the Sunday market the following morning
 
Not realising a J24 is so twitchy. Unlike anything else I have sailed on in my limited sailing career, I did not know that they will not dip the rail in and ride out a gust.

2 broaches in 5 mins lol.

In the gusts we never dump our main or luff up. She just goes faster and we get a bit wetter!!
 
A big, big thank you to everyone who contributed to this thread. I read and enjoyed every entry. For those of you who allowed me to use your post on my blog I thank you and have now published it.
 
Many many years ago (1989??) I was doing the RYA Young skippers scheme. First day, I was skipper, keen to make a good impression.

All coming into mayflower in engineless boats which involved a long shoot to windward before coming to a stop 3 inches from the pontoon to be met with the question, where are your mooring lines? Cue mad panic to find lines to secure to the marina.
 
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