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

There are limits to my willingness to confess but one entertaining event occurred after we were lifted off the Sunk by the tide at about two in the morning and continued on our way towards Ramsgate. This was long before Decca let alone GPS. My navigation was in difficulty because the flashing red of E Margate buoy didn't match what the chart said. It wasn't until we were almost round N Foreland that the mysterious light changed to white as we left the red sector of the N Foreland light.
 
Clearly the honest answer is stepping on board after buying it.
I will now wash my mouth out with beer...
No, No - the honest answer is buying it in the first place then thinking "WTF have I done?" or ...... not running away when the broker took out the paperwork, the bill of sale and his pen.
 
One of those I'll admit to...

After a Channel crossing from Salcombe to St Peter Port with no autohelm or electronic aids apart from RDF I was utterly knackered and crashed out with my non-sailor girlfriend, only to be awoken at 02:00 by boats rafted inside of us going into the marina from our waiting pontoon as the tide allowed.

I thought I might as well go in too and didn't bother waking g/f.

I found in the morning I'd carefully tied the springs from our bow to our stern, ditto on the neighbouring boat, don't remember what I did with the bow & stern lines but we were just hovering alongside in the calm water when I surfaced mid-morning.
 
Coming in from a race into a fairly tight marina we were all standing on the port side drinking cans of beer and causing a severe list. Caught the masthead of another boat with ours and ripped off his windex. We bought the owner a new one and offered to fit it that afternoon. He took one look at out inebriated state and decided he had better get up there and do it himself.
 
Purely by luck, my many 'idiotic mistakes' have rarely turned into 'biggest cock-ups'. Leaving aside boat purchases/sales, memorable ones include -

1) Getting my first boat, a dinghy, home, I started to put the mast up to see how nice it looked. Remembered only in the nick of time the electricity cables low overhead.

2) Enjoying a boisterous sail, overcanvassed and lee rail under, Dartmouth to Salcombe, deliberately going through the race off Start Point to crash through the waves, only to discover I'd left the diesel cap off when we'd refueled before leaving, flooding the tank with seawater.

3) Arriving very tired and single-handed at L'Aberwrach. Hung around in the river for a while nervously calculating approach to pontoons. Fixed outboard astern of rudder (Hurley 22) meant no steering unless moving forward decisively, and negligible braking power and nil steering in astern. Having selected the least worst of the awkward berths available, and tried to weigh up the wind, current, etc., I headed in, now commmitted with no available plan B or means of aborting the attempt. As I made the final sharp turn necessary, I thought, with the benefit of hindsight, I could have managed with slightly less speed. At this point I also realised I had forgotten to put any fenders out! I put the engine in astern to take off what speed I could (a largely symbolic action), got the coiled rope ready on my hand, lined the boat up, leapt for the finger to get a rope round a cleat, caught my foot on the guardwire and fell flat on my face! I gritted my teeth for the inevitable crash of bow on pontoon, and could see myself being dragged into the water as the outboard in astern finally achieved some grip and the boat headed off in some random, vaguely astern direction towards any of the surrounding boats. None of which actually happened, as some French sailors had seen my ill-starred approach, and had leapt to hold the bow off the pontoon, and then hung on to it while I picked myself up, got a rope on, and outboard into neutral. Fenders went out later when I had recovered my composure and no-one was looking.
 
Installing a lee cloth to the inside of hull by drilling a series of holes through a stringer. Last one was very difficult but I managed it.

Then realized it had been difficult because I'd drilled through the hull, not the stringer. Fortunately about two inches above the waterline. Whew.
 
All my mistakes have been idiotic - are there any other kinds?

My most dangerous was when we moored stern-to our own anchor in a bay at the south-west corner of Gocek Bay in Turkey. When we arrived the only available spot was in the corner of this U-shaped bay, I congratulated myself on getting in there and getting the shorelines on without hitting the rocks (about 3m away on our starboard side) completely forgetting that it was flat calm at the time with no wind at all. The next day everyone else left.

My first mistake was in not wondering why they'd all left.

My second (and almost catastrophic) mistake was in not moving to a safer spot in the centre of the bay.

That evening the winds and seas grew, the swell was coming from the south, reflecting off the opposite shore and relentlessly pushing us onto the rocks. Leaving was impossible, we'd have been on the rocks in a heartbeat and even leaving the anchor behind would not have helped, plus it was already getting dark and this was a remote bay with no lights. We put out every shore-line we had and the other two anchors from the dinghy, the old 60lb CQR straight into the direction of the swell. We got no sleep, we had everything packed ready for a swift leap onto the rocks when the anchors let go. I can still feel the sense of helpless terror and the certainty that we were about to lose the boat and there was nothing I could do about it.

By the morning it was apparent that the weather was abating, the swell was not as strong and the sky began to clear. By 10am it was calm enough for us to get out, and we did - rapidly! Never again have I moored stern-to my own anchor without enough room to let the shore-lines go, swing to the wind or swell, and get out.
 
Motor sailing I set the autopilot on leaving Cascais (Portugal), I was about a mile offshore with no boats about so went below to put kettle on but discovered gas cylinder was shut off so climbed back into cockpit and opened gas cylinder valve but inadvertently and without realising it, knocked the autopilot ram off the tiller pin, I returned below to resume galley chores. After 10minutes (or whatever) decided to pop head out of cockpit for a quick look around and discovered I was heading directly for land and (I'm guessing)was less than a 100 yards off. I leapt at the tiller, put it hard down, shut my eyes, gritted my teeth and prayed to some unknown God. The V27 is a long keeler and doesn't turn on a sixpence but after what seemed an eternity the boat turned and headed offshore just avoiding disaster.
 
3) Arriving very tired and single-handed at L'Aberwrach. Hung around in the river for a while nervously calculating approach to pontoons. Fixed outboard astern of rudder (Hurley 22) meant no steering unless moving forward decisively, and negligible braking power and nil steering in astern. Having selected the least worst of the awkward berths available, and tried to weigh up the wind, current, etc., I headed in, now commmitted with no available plan B or means of aborting the attempt. As I made the final sharp turn necessary, I thought, with the benefit of hindsight, I could have managed with slightly less speed. At this point I also realised I had forgotten to put any fenders out! I put the engine in astern to take off what speed I could (a largely symbolic action), got the coiled rope ready on my hand, lined the boat up, leapt for the finger to get a rope round a cleat, caught my foot on the guardwire and fell flat on my face! I gritted my teeth for the inevitable crash of bow on pontoon, and could see myself being dragged into the water as the outboard in astern finally achieved some grip and the boat headed off in some random, vaguely astern direction towards any of the surrounding boats. None of which actually happened, as some French sailors had seen my ill-starred approach, and had leapt to hold the bow off the pontoon, and then hung on to it while I picked myself up, got a rope on, and outboard into neutral. Fenders went out later when I had recovered my composure and no-one was looking.

Being French they probably thought that a perfectly normal berthing manoeuvre :D

Meanwhile I have just got on board to find the dehumidifier working away but the pipe I use to drain into the sink still in the locker
 
You think I'm going tell everyone here THAT???? !!!!

One of my milder ones was to let-go the warp from masthead to quay bollard before the tide had come back in far enough.
The boat had been properly leaning slightly shore-wards when dried-out for scrubbing, with said masthead warp taken to bollard , "just to be safe and sensible". But as the tide came in the "off-quay" breeze had picked-up .
I was in a mild hurry to clear the harbour and get back home. I hadn't noticed (or thought to THINK) that as I released the warp said boat was now leaning ever-so-slightly "outwards".
WHHOOOOSH, over she went onto her beam-ends.
Two fortunate things.
Firstly, there were no boats, harbour-walls, buildings to leeward.
Secondly, only one person saw it happen - and I'm hardly going to criticise myself, am I? !!
 
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I was in a mild hurry to clear the harbour and get back home. I hadn't noticed (or thought to THINK) that as I released the warp said boat was now leaning ever-so-slightly "outwards".
WHHOOOOSH, over she went onto her beam-ends.

I once dried out at Peel so delicately balanced that the act of reaching across the boat to pick up my alarm clock sent her over - luckily into a foot of water, which cushioned the blow. I improved my tying up technique after that.
 
Not buying a small scale chart for an extended cruise and hitting the rocks on Christmas Day. Big Bang, small leak and 100 miles offshore to get somewhere where we could get her out of the water.

Using my foot as a fender when I got leaving the marina a bit wrong. No damage to either boat, but had my foot in plaster for 5 weeks.
 
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