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Embarrassment of cringes

Phil Herring

Dethroned Admin
Mar 25, 1997
Hunter 450 Bainbridge Island
Sometimes there's nothing to do but own it.

That moment when the bitter end of your rode followed the anchor into the water. The day you snagged your mast on a bridge. Or perhaps when the Coast Guard found those flares that expired in 1974.

We've all learned humility on the water and now it's time to share your most embarrassing nautical mishap.

Double internet points for a large audience. Triple internet points for photos.

Feb 3, 2015
Marlow Hunter 37 Reefpoint Marina Racine, WI
Docking gone bad. No photos! I just had bow thrusters installed. Backing into slip with some wind. She’s version is I wound up nicely perpendicular to the finger dock looking like a cruise ship. What actually happened was an overzealous bow line yankee combined with (unknown to me at the moment) that the wiring for the bow thrusters ran right through the port side stop to the wheel. When I turned hard to port, the port starboard side of the thruster would go entirely unknown to me at the time. After getting finally, I figured out all that went wrong. U next docking after fixing the wiring and banning the line yankee went perfectly. Good thing as my boat neighbor was there videoing me on his iPhone!


Alden Forum Moderator
Jun 22, 2004
Alden 38' Challenger yawl Rockport Harbor
I don't photograph my own, Phil. But we're all voyeurs of other boaters, especially newbs.

Working on my boat a few springs back, I watched this shiny new runabout come into the public docks. The couple looked proud as punch. When I saw her climb up on the bow holding the dock line, I put my varnish brush down and grabbed my camera.

A few feet off the docks, 'skip' hit reverse, .... followed by a splash.

I only had the heart to snap one photo but I think this image says it all.

New boat owners crop (1 of 1).jpg


Mar 23, 2017
Belliure 41 Snug Harbor, Lake Champlain
It was a lovely summer day and I'd been out sailing. Coming back into port towards evening there was rather a line of boats making their way into port. I doused my sails and fired up the motor and positioned myself in the imaginary line-up. The going in was a bit slow as boats were passing the entrance, two huge rock walls making a narrow entrance into the port. Two smallish boats could pass side by side, but usually it was one boat at a time.

As I'm slowly motoring with appropriate space between me and the boat ahead of me, I notice a small runabout coming up behind me, a bit fast for the situation. Then I see him swerve port and starboard of me a couple times, obviously to see past me, I'm on a fairly good sized sailboat...

We are all approaching the harbor entrance and there is now one boat in front of me before I'll get to the restricted entrance. I hear the runabout gun his motor and move to pass me on my starboard side. Well, I guess I could have backed off in my throttle, but I didn't. I also didn't accelerate either, although I was bloody well tempted...

So there he went flying by me to beat me into the port, but it takes longer than one thinks to pass a sailboat... So he actually broadsided his boat into the rock wall, bounced off and did indeed make it into port ahead of me. I would imagine to cost of fixing his boat after was one of those "expensive life lessons" that we all go through.



Sep 7, 2015
Hunter 25.5 Longboat Key
About 1984 I wanted to go under the Kingsferry Bridge in my 20 footer on the River Swale in Kent, England. The bridge was a road/rail bridge which only lifted when the line was clear of trains and would then open 'on demand'. As so few small boats had VHF, the accepted method of requesting an opening was to raise a bucket on a halyard. I waited ages, through several trains, I could see long gaps in trains, but no opening so very rashly decided to risk going through. I was conscious of a long delay could mean I missed the tide to reach my drying mooring over 4 hours away. It would have worked at a lower tide but the forestay caught on the bridge. Bow went up a foot or so, and the top of the mast went under and was trapped in the girders. I had to wait at least another 15 minutes before the bridge finally lifted. The jib roller spar had a bit of a kink in it which I eventually straightened. The permanent damage though was to my pride. Patience, and a VHF to give me communication to the bridge keeper would have prevented this.
Interestingly I've read that although the railway is electrified the bridge section is not, so I suppose if a railway engine was to stop mid-bridge, it wouldn't be able to drive off!
Apr 5, 2009
Catalina '88 C30 tr/bs Oak Harbor, WA
Back when I was on Lake Coeur d' Alene, My sister came for a visit and we were doing the Lake Home Parade. This is a traditional cruise, paralleling the shoreline to look at all of the lake mansions and we were all on the bow and I was steering with the AP remote. As we came around Arrow Point the shore line makes a 180º turn to port so my plan was to do a series of (3) -10º bumps to the the remote to make the turn. Very cool. The first two when just fine but after the third, the boat just kept turning to port after the expected 30º turn.
I sprinted back to the helm and disengaged the helm, just in time to run straight into the shoreline which is a solid rock incline that approaches the shore at a steep angle. D'oh! :facepalm:
We were stuck fast and this was during the lakes annual "tide" when they draw down the lake to its winter level so the water was dropping about 12" per day. We had our dinghy with us so I loaded my CQR into it and rowed it out to the full length of the rode which was about 250' and let it free drop to the bottom in about 150' of water.
I then winched the rode back in until the anchor hooked the rock face and then let out the spinnaker halyard as far as it would go and tied it to the bite of the rode with a prusik knot and winched the spin halyard as tight as I dared. This gave me about 15º of heel but we were still stuck hard. The home-owner of the house on the point happened to see my predicament and came out with her jet ski to see if she could help. I aske if she could take hold of the anchor line where it came out of the water and give a tug parallel to the line, bow-stringing it.
She drove under the line just after it came out of the water and grabbed the line with one hand and gave the jet ski a bit of gas which caused us to heal to over 25º and we popped off. :clap: Lots of fun pulling a 35lb CQR up from 150' with the windlass not working. :kick: But then I was just happy that it came free from the rock when I pulled it in the opposite direction.
That happened to be the one and only day that I had my scuba gear on board because I had been looking for a pair of very expensive sunglasses that a friend had dropped overboard. I When to the nearest bay and dove to check the keel for damage. Everything looked fine (except for that 1" deep groove in the lead where we hit. :banghead::banghead::banghead:
May 1, 2011
Pearson 37 Lusby MD
I don't have any photos, but there were witnesses, including the marina manager.

It took me three years to get up the courage to take my boat out solo. Part of the reason was the narrow fairway between my dock and the next one over, probably around 40 feet for my 37' sailboat. Anyway, got out just fine. Got the sails up and had a glorious time. I knew I'd need to get off the water early because the wind was supposed to pipe up.

Time to douse the sails. Furled the genoa and set the autopilot into the wind so I could go forward to drop the main. As I was standing in front of the mast, I watched my wake - not straight, but a series of S shapes. Started cussing out the autopilot. Got the main down safely and went back to the cockpit. Turned off the autopilot and realized the helm was only responsive in one direction. Got it, the steering cables had come off the quadrant.

I had to deal with the same problem earlier with crew, so knew what to do. Easy fix, right? Wrong! :banghead:I'd had new cables installed during the winter refit and couldn't get them back on the quadrant because they were correctly adjusted so they couldn't slip off. I could get one on, but not the other. In the meantime, the wind is piping up as predicted. So the only way to go in is with the emergency tiller. I should point out that the wind was behind me, so the not quite stowed main gave me a little more sail area than if the sailpack was completely zipped up.

So to cut to the chase, I ended up one slip farther in (depth sounder going nuts!) on the opposite side of the fairway and stern first. The marina manager told me he'd get me some help so I could get into my own slip. While I was waiting, I managed to get both cables back on the quadrant. When I got back to my slip, the marina manager opined that if I was going to continue going solo, he'd have to get me another slip. He did, and now I have a fairway that's at least a boatlength and a half. No more sliding into home to dock the boat. Cringe worthy? Absolutely. Did I learn something? Absolutely! Did I have an audience? Yes. :beer::beer::beer:
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Sep 11, 2015
Merit 22- Oregon lakes
After reading some of the other adventures I don't feel so bad about my own anymore :biggrin:. my latest was just last week wile out on a lake for three days. the second night out we found a nice cove and tucked in to it for the night. when I was over the perfect depth and location to anchor I tossed it over, but the rode didn't follow. first time overnighting on this boat and hadn't wanted to swap over the anchor gear from the other boat so I had just tied a couple old sheets and halyards onto a spare anchor. guess I should have tied better knots :redface::laugh:
Jul 23, 2019
Hunter 18.5 Revelstoke
Day 1 on my new to me Flying Junior and just learning to sail, all was going extremely well till I tried to squeak under the highway bridge. Going in I was healed over enough for clearance for the mast... great! Then I was deep enough in to be in the wind shadow and the boat stood up and the mast caught the bottom of the bridge and the rodeo was on.


Jun 29, 2014
S2 7.3 Fond du Lac
No pics, but witnesses.....I got stuck on a sandbar I knew was there-it was right in front of the house I grew up in.

I took a lady sailing for our first date and decided to show her where I grew up. Now my boat draws 4' and the lake is 8-12' deep right up to the 3'6" sandbar 100 yards from shore.

I was busy playing tour guide pointing out the house and other points of interest. I also may have been just a wee bit distracted by her in a bikini when the boat came to a dead stop-which wasn't the worst thing because she was sitting aft of me and inertia pushed her into me:thumbup:. Unfortunately I knew right away what happened (as a kid I swam out to this sandbar several times a year since I could swim). I tried healing the boat, reverse, etc and it wouldn't budge. Finally, as a last resort I called my brother, who I knew was nearby in his Malibu ski boat with his family, to come to the rescue. They showed up laughing, introduced themselves to the lady, and pulled us off the bar.

It wasn't a deal breaker with the lady, we were together for several years, but that's a different, nonsailing story.....
Oct 24, 2010
Hunter 30 Everett, WA
Years ago. Crowded boat launch. I made ready for the launch ramp by pumping out our water ballast, pulled up the daggerboard, put out fenders etc. Now I could pull the boat out quickly to fee up the ramp. The issue was when I tried to steer around the dock so I could climb off to get the vehicle and trailer. The boat went sideways right into the corner of the dock which was crowded with witnesses. Never pull the board up if you need to steer.

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Oct 22, 2014
CAL 35 Cruiser moored EVERETT WA
John... What makes you think you know so much about boat fuels systems, diesel bugs, and clogged filters.


I've shared on these pages, the story of my meeting in the fog with a fishing boat doing 30 mph trying to get to his fishing grounds.

The fishing boat crash was just the beginning.

Having cleared Admiralty Inlet we started out across the Juan D'Fuca Strait. The water was flat, the sun was shining and after the harrowing experience, I let the adrenalin of the past 90 minutes seep away. I watched my buddy boat Mahalo alter course a bit to the north. No problem we have nearly 20 miles to go across the strait. I was just beginning to relax when I heard a horn blaring. I jumped up and there directly ahead of me was a fishing boat, in the middle of the Strait. I was heading directly at him. Only this time it was me causing the danger.

Fortunately, we both reacted positively, Me altering course and he pulling up on his anchor. As I passed, I heard many derogatory declarations about my lack of seaman ship and navigational skills.

By now I thought I had been fully baptized in negative experiences and survived. Nothing more could spoil this day...

Bad things always happens in 3's say wise men.

Sure enough, about 30 minutes later my engine starts to cough. Bugger. I am out in the middle of the Juan D'Fuca strait. Cruising Solo, and the fuel line is clogged. I shout to @LeslieTroyer - "Hey Mahalo. I got a fuel problem. I am going to shut down and change the filter." All Stop. Down in to the engine compartment. Shut off the fuel line. Pull out the filter. Sure enough clogged. Pop in the new filter. Fill the Racor from my spare fuel. 15 minutes pretty good time. Try to start the engine. Out standing - she starts. Smiles all around no need to prime. Off we go. Onward towards Roach Harbor.

5 minutes later.... Cough. sputter. silence. Poo. What now? Damn.... I forgot to open the fuel line before I started the engine. Click the VHF Mic... "Mahalo, I got another problem. I need to prime the engine. Last time it took 20 plus minutes. You want to go ahead?" " Hadley, Why don't I throw you a line and I'll give you a tow. My wife can steer your boat while you fix the engine." "Ok"... Mahalo comes up close, Trish jumps aboard. I tie off the tow line. Les pulls Mahalo out into the lead. Trish and I chat about steering with the tow line, and then I go back to the engine room to open the fuel line. Manually pushing the lift pump to bleed the engine, eventually I get fuel to the injectors.

30 minutes later I get the engine going. We release the tow. And for some strange reason Les does not want to get close so Trish can return to Mahalo too dangerous....

Trish and I enjoy the rest of the trip, she at the helm most of the run.

The day eventually ends with us in Roche Harbor eating a great meal and sipping from a bottle of fine Cab.

Diesel Fuel systems, I have learned by trial and error.
Jul 5, 2011
Oday 28 Madison, CT
1980's Norwalk, CT harbor. Lost control of an O'Day 25 trying to do too many things, showing stuff to a novice sailor in a tight mooring area, lost control of the boom which hit her in the head and knocked her overboard. Rush to hospital, happily big bump but nothing worse. I learned a lot from that and she still spoke to me...amazingly.


May 5, 2018
Macgregor 25 Home
Just today, I took my new built 10‘ spindrift dinghy out to the lake for a test sail. All good, learning how this boat feels and reacts, after an hour or so, I decide I want to head in. As far as I can recall, I did a bad gybe with the intention of running downwind to the put in. There May have been a gust, and I capsized. the water was warm, I had my PFD, so no panic. I right the boat, but the sail catches wind, and it capsizes again. flip it back, drop the sail, and realize I have not bothered to bring a bailer, so it’s holding my weight in water. So, I grab the painter and start swimming to the shore that was maybe 200:feet away. A SUP rider comes by, and gives me a tow to shore. From there, I walked in the shallows around the lake with my flooded boat in tow. Nothing damaged but my ego. I lost my hat though.



Aug 10, 2014
Catalina 22 9874 Newberg, OR / Olympia, WA
Well, I think my best one was already documented here, but I'll add another I don't think I ever mentioned:

We'd just acquired a Walker Bay 8 dink with a sail rig (subsequently dubbed 'Wisp' by popular vote of the household's under-10 crowd). For her first sail, we took her to a familiar lake. 8 feet is pretty small, and the sail rig doesn't leave much room for crew, so I left my wife and daughter onshore and headed out with only my 5-year-old son. The dock was pretty busy, so we just rolled her down to the bank on her stern wheel. I rigged the sail, knowing that we'd have to row a bit against the breeze to find water deep enough to drop the daggerboard and attach the rudder. I demonstrated the daggerboard process to my son, leaving myself the task of leaning over the transom to drop the rudder into its gudgeons.

All went according to plan (or so I thought).
1) Row out 100' or so
2) Tell my 5-year-old crew to drop the daggerboard
3) Attach the rudder
4) Grab the sheet, and off we go...

The daggerboard and rudder took a few seconds, and the stiff breeze had of course, pushed us back toward shore. But that's no problem - we're sailing now... Wait. What the ?#$%$&*# ? Will she really not point any better than this? :poop: Even on a beam reach, which should parallel the shoreline, we're making a lot of leeway, and drifting rapidly toward the rocks. And none of my novice sail-trimming tricks seem to make any difference.

After far too long, I realized that - while I was turned around to attach the rudder - my son had 1) Dropped in the daggerboard properly; 2) Observed the shoreline approaching (with shallow water and rocks); and 3) Pulled the daggerboard back out to avoid crunching it if and when we grounded.

Sensible kid. But it would have been nice if he'd mentioned that fact...

So no, a WB-8 still isn't much for sailing on the wind. but she does do a lot better with the daggerboard down! :facepalm:
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