Gentlemen... your most embarassing sailing moment if you please. - Page 3 - SailNet Community
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post #21 of 81 Old 11-05-2007
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Ok, I will chime in with my most embarrasing (and stupid) moment:

Me, mom, dad, and my wife were anchored off of some island in S Florida (don't remember which one now). We invited mom and dad down with us to experience the beauty of cruising and life on a sailboat. It was a warm Florida night, all the hatches were open, we were playing cards - and life was wonderful. However...

The distant smell of the head kept creeping into the cabin. I was concerned that the tank was leaking so opened up the board and looked at it. Sure enough, there was a very small drip. I quickly closed it and told mom and dad everything would be fine. I did not want to tell them the head was dripping SH** in the hold. After all, I am trying to convince them to sell everything and go cruising with us. You know, nothing but margaritas and sunsets.

As I had already drank about three margaritas, a great plan suddenly hit me: Go outside and take the top off the holding tank lid so the smell would dissipate outside. I finished my turn at cards, quietly excused myself, walked outside, and popped open the lid.

What happened next was a sight I will never forget:




Mom, dad, and Kris came running out of the salon and outside of the boat with their noses in their shirts and gasping for air. Apparently that stench is heavier than air so the holding tank belched and it was sucked down below.

THeir eyes were watering, I though Kris was going to be sick... and dad was cursing me.

HEHE!! Oh well. We were able to return down below later that night!! And believe it or not, they are still going cruising with us!!!

- CD

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post #22 of 81 Old 11-06-2007
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I apologize that this was written for another venue and is a bit long. It’s hard to describe my most embarassing sailing experience but it might also be one of my most memorable as well. Frankly, I have been blessed with a lifetime of ‘most memorable’ sailing experiences and cursed with a fair number of embarassing ones as well. Perhaps the one that comes most strongly to mind is my first sail on Diana, my Folkboat. After graduating from college, I had purchased ‘Diana’ as a derelict, and a near wreck. I had spent seven months restoring her to sailing condition. I had replaced the rig, rudder, and keel bolts. I had sistered the frames, replaced some floor timbers and planking, constructed a new cockpit and interior, replaced a piece of the stem and the forward face of the cabin, had wooded the bottom and repainted her inside and out.

As 1973 raced to an end, my yard bill was paid up through December 31st, and I had decided that I would get the old girl launched in time for the New Year. As it worked out the yard closed down on Christmas Eve and would not open again until January 2. So, it was that ‘Diana’ was splashed on Christmas Eve.

‘Diana’ was a lapstrake wooden Folkboat. Having been out of the water for so long, her planking had dried out and her seams had opened up so wide that you could pass a thick piece of cardboard through them. There is a process to launching a boat that has been out of the water for that long that amounts to nearly sinking the boat for a day or so, but that is story for another time. Even after the seams have seemingly swelled close again, the theory with a wooden boat that has been out of the water for a long period of time, is that you must let them swell in the water for another week or so before you sail them. Since much of the strength and stiffness of a wooden boat comes from the friction between the planks, this swelling period allows the planks to swell hard against each other.

I spent the week bailing, finishing the rigging, and working on fabricating the new cockpit and interior for the boat. To keep ‘Diana’ from sinking, I was sleeping aboard. I slept on a slatted grate that I had made as a temporary cabin sole with my foot hanging into the bilge so that the rising water would wake me and I would know to bail.

In a week that passed before I noticed that it had even started, it was suddenly New Years Eve and I had to get the boat out of the boatyard. With a week in the water, the leaking had pretty well stopped. I had been given permission to tie up for free between an old piling and a bulkhead on the edge of the boatyard out of the everyone’s way. I figured as long as I had to sail over to the new slipway, I might as well go out for a sail first.

This was my first sail on the Folkboat, and my first sail as the skipper of my own keel boat, and only the second time that I had single-handed a boat this big, and the first time I had single-handed at night. I slipped out just as the sun was setting in a classic sky-on-fire Florida sunset, beating east in a light ghosting breeze beneath a Jack-o-lantern of a sky. I sailed quietly toward a blood red rising moon in an ever darkening evening toward the pass at the southern end of Key Biscayne.

Now a Folkboat is a marvelous little boat, which as I discovered that night, can sail herself seemingly for days at a time; just trim, aim and off she goes. I sat up on the cabin top, jib sheet in hand; steering off the wind by tightening the sheet and heading up with an ease of the sheet. These were simpler times and quieter times. I had Biscayne Bay to myself; no running lights to be seen anywhere. ‘Diana’ was free of anything that one might call modern. She did not have an engine and so did not have an electrical system or running lights. Being a few inches less than 25 feet on deck, I simply carried the legally required flashlight, which I was prepared to shine on my sails if another boat appeared in the night. The head was a simple ‘bucket and chuck it’ system. She lack lifelines and stanchions, and the deck hard was crude and underpowered but reliable.

To those of you who have spent much time single-handing after dark, you will probably know what I mean, when I say there is nothing quite like the emotional sensation of being alone at night at sea. There is this profound sense of being more alone than you have ever been in your life. There is a sense of tranquility and a sense of speed that is far beyond that felt in the light of day. There’s a sense of self-reliance and sense of a fear that comes from realizing that it is up to only you to make the right or wrong decisions out there and if your decisions are wrong it is only you who pays the consequences. The carpet of stars overhead lit the sea and their distance made me seem infinitesimally small, and humbly insignificant.

I sailed for hours into the chill moderate breezes, but around ten or so, I reached the mouth of the cut into the ocean and turned back for home on a nice broad reach and a building breeze. The trip back into the lights of Dinner Key is lost to my memory but when I arrived at the harbor I began to sort through my possibilities. It suddenly had occurred to me that I had never brought a boat this big into a dock alone under sail. I sailed back out into the mooring area, and practiced a couple approaches to the piling. I decided my best bet was to approach a couple boat lengths to leeward on a beam reach and then head up into the wind. I had decided that there was no way that I could be on the helm and still make it forward in time to place a line over the piling. Somehow, seen through the rose colored optimism of youth, it made great sense to me to steer in controlling the direction of the boat with the jibsheet while sitting on the foredeck. If I missed the piling I would fetch up on sand bar just ahead of the piling. Now youth is an amazing thing, you have not learned enough to know what you don’t and may never know. Youth brings a confidence that can only come when you don’t know the consequences of making a really big mistake.

So in my youthful confidence I came roaring in on a beam reach, sitting on the foredeck, jib sheet in hand. At the moment of truth, I freed the jib sheet and Diana pirouetted gracefully up into the wind. I grabbed the clew of the jib and moving it from side to side, steering and slowing the boat. Coming to a dead stop right next to the piling. Polite as you may, I threw a bight of a dockline over the piling. And there I stood, dockline in hand, congratulating myself on a job well done. I stood there cold and numb; a toothy grin across my face, scanning the docks for some sign of life; some witness to my brilliant feat of seamanship. No good deed goes unpunished and in my moment of self-congratulatory elation, nature took its turn to take me down a peg or two, hitting Diana with a big puff from the opposite side of the jib from where I stood on the narrow foredeck, pushing me hard towards the rail. As I went over the side, I dove for the shrouds, grabbing the upper shroud with my forearm, slicing it deeply on the Nicropress fitting that should have been taped for just such a reason, dropping feet first into the cold waters of Biscayne Bay in December but keeping my grip on boat.

As I hung over the side, legs in the water, I tried to decide whether to let go and fall backwards into the water, or pull myself aboard. Remembering a check in my wallet in my pocket, I pulled myself aboard. My scream as I went over the side had roused a crowd from the boats tied up nearby; a crowd that arrived just as I pulled myself from the water. As I lay there on the foredeck, winded and bleeding, soaked and shivering; the sound of fireworks and firecrackers bursting in the distant darkness and a chorus of Auld Lang Sine from the drunks in local juke joint wafted out to tell me that I just had entered into the brand New Year.


Last edited by Jeff_H; 11-14-2007 at 01:47 PM.
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post #23 of 81 Old 11-11-2007
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GREAT story Jeff! I have found, like you, that it rarely takes long to get knocked off whatever pedastal you've imagined yourself to be on. I'm still laughing picturing you standing on deck, looking for witnesses! Thanks, John

SV Laurie Anne

1988 Brewer 40 Pilothouse

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post #24 of 81 Old 11-12-2007
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There have been so many how do I pick just one? I think the MOST embarrassing would have to be about 10 years ago as a newbie sailor on Puget Sound. I was singlehanding one rather blustery fall weekend and was pulling up to a floating fuel dock at Point Defiance. The dock was little more than a steel barge, with a very smooth, wet and slippery deck. The wind was up that day around 20+ and the sea had a good 2-3 ft chop and the dock was bobbing like a cork.

I motored up to the dock and tried to position the boat close enough to make the leap of faith. With mooring lines in hand I jumped for the dock. Did I mentioned the dock was wet and slick as ice from a thin film of diesel? Well, I promptly landed flat on my back and dropped the mooring lines in the drink.

As the boat continued on its way without me I quickly reached out for the cockpit gunwhale to grab the stern line and found myself in that classic and precarious position of “hands on boat- feet on dock” and as the gap between the boat and dock widened I felt that familiar “uh-oh” in the pit of my stomach and a second later found myself in the water.

I swam toward the boat and grabbed the stern line, and luckily there was a ladder welded to the dock, for just such an occasion I assume. I managed to wrangle the boat back to the dock and tie her off as I noticed a group of onlookers up on the wharf. I promptly went below to hide and put on some dry clothes.

Not my proudest moment!
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post #25 of 81 Old 11-12-2007
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Another one worth mentioning is another time about 5 years ago on a friends newly purchased S2 30’ center cockpit with a bum motor. He had the brilliant idea of installing an outboard motor WITHOUT remote controls on a stern bracket as a temporary alternative to replacing the inboard diesel.

Well this configuration was wrought with peril. The least of which was that it took two people to operate. The helmsman (my friend) had to shout commands back to the motor operator (me) as I hung precariously off the aft cabin top and reached down to control the throttle.

It was time to test the new motor. After a fairly graceful exit from the slip we got underway and enjoyed a nice day of sailing. Our re-entry to slip was not as graceful. Now keep in mind that I couldn’t hear a damn thing hanging off the stern with my head down near the motor and had to pull myself back up to hear anything, not mention that I couldn’t see what was in front of us either.

Being very cautious I was gentle on the throttle and heaved myself back up to see how things were going and he said to “give it a little more” so I did. A few seconds later I thought I heard some yelling so I pulled myself back up to hear him screaming


I frantically shifted into reverse and gunned it and the motor tilted up and the prop came of the water as the RPM’s maxed out. Needless to say we crashed head on into the dock and put a nice gash in the bow.

If the image of the Keystone Cops on a boat comes to mind that would be fairly accurate.

Not surprisingly, the very next weekend he came wheeling a new used motor down to the dock, the installation of which was another keystone cop episode!
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post #26 of 81 Old 11-12-2007
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I had an outboard do that on my little boat once. Luckily, we didn't hit anything.
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post #27 of 81 Old 12-05-2007
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That's not so embarrassing for you...for her though...


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Telstar 28
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.

—Cpt. Mal Reynolds, Serenity (edited)

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post #28 of 81 Old 12-05-2007
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Anton, what a great story. Thanks for the morning laugh.

S/V Scheherazade
I had a dream, I was sailing, I was happy, I was even smiling. Then I looked down and saw that I was on a multi-hull and woke up suddenly in a cold sweat.
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post #29 of 81 Old 03-24-2008
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Saling Gipsy moth 4 i the small ships raced an sweden 42 up our arsewhen he decided to tack, he caught his anchor around our mizzen backstay and we hinged together. more embarassing for him than us but at least it was 2 pictures in the paper.
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post #30 of 81 Old 03-24-2008
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Red face

O.k one more. Out in Antigua we were sailing a elan 45. Out on the piss 1 night when finally we headed back to english habour. we jumped on our boat (or so we thought) and crashed. me in the galley one other crew member in his suspected cabin. I Was awoken at 6 in the morning not with the usual smiling chef and her cup of tea ready but a 6 foot police officer brandishing his shotgun. After two hours in a cell and a lot of barganing from the skipper we were finally released with no charge we did have to appologise to the owner who was very understanding, as really he should have locked his boat.
However we were on head duty for the week for causing the boat to lose a day. NEVER AGAIN
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