Embarrassing Moments

Phil Herring

Dethroned Admin
Mar 25, 1997
Hunter 450 Bainbridge Island
What a great day to share an embarrassing story about yourself!

C'mon, everybody has them. Own it. Celebrate it! Share the most humiliating moment you've had on your boat.

After all, we have much to learn from your mistakes.
Jan 7, 2011
Oday 322 East Chicago, IN
Well, I answered the survey, and picked “Docking”…

I was leaving my slip, single-handed, backing out pretty fast to keep from being blown sideways in my slip…
When “boom”…the boat lurches toward the dock and stops abruptly…
Forgot to slip off one of the spring lines…and when it pulled tight…well you can imagine the rest.

I looked around, didn’t see any spectators, eased back into my slip and gracefully slipped off the spring line and backed out again…

Oct 26, 2008
Catalina 320 Barnegat, NJ
Late last fall I was leaving the dock with a friend at the marina. I always lock down my wheel with a rope or bungy and I forgot to release it when I called for my friend to cast off at the bow and I released the windward stern line. I quick went to neutral after starting to move in reverse so I could release my wheel. We had a pretty good cross wind and it quickly took my stern and pivoted the boat around our short finger piers. The pilings were just beyond my stern and I quickly went broadside to the piles between the finger piers and the pilings. It was late in the fall and almost all boats were out of the water. I was in jail since the pilings are spaced about 12' apart and my boat is 32' long. I couldn't get out of jail because the finger piers limited my ability to position my stern (they are about 24' apart - the width of 2 boats). Luckily there was one space with a missing piling and we were able to slip out into the fairway! My friend thought it was pretty funny and he couldn't believe that it was actually possible to maneuver my boat to get stuck inside the pilings!


Jan 20, 2005
Nauticat 321 pilothouse 32 Erie PA
well, it was our first 'big boat'-- a 1980 Rhodes 30 foot sloop rig Seafarer , with a v berth, 2 sinks , a head, a v berth, a galley... so excited ! what an upgrade from the old cal 20 ! we bought the Seafarer from our boat neighbor Moe, who'd gone to the 'dark side' w a 40 foot jefferson. our first week end on the new-to-us boat, , the freshwater par -jabsco diaphragm pump wasn't supplying the galley sink too well. so i cleverly opened the top of the huge 20 gallon freshwater tank located under the v berth cushions and observed it to be nearly empty. so i cleverly went on deck, installed the dock's water hose into the deck fill marked 'water' , and started filling. The spouse was lounging below at the dining table, feet up, reading. suddenly i heard a yell, 'stop whatever you're doing, , would you be interested to know you're causing a flood??' ! Moe had disconnected the hose from the deck 'water' fill into the fresh water tank, and neglected to tell us he always filled the tank by installing the hose thru the forward hatch direct into the tank so he could watch the tank fill.. at least the teak and holly floor got very clean, and the bilge pump got a good work out...
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Feb 20, 2011
Island Packet 35 Tucson, AZ/San Carlos, MX
Once I forgot to unhook the pigtail from the backstay to the boom on the Mac.
Got lucky.
How many things do we only do once?


Feb 11, 2017
Islander Freeport 36 Ottawa
Many years ago I sailed on the Bounty out of Sydney Harbour. The ship was built to the original lines of the 1784 HMS Bounty but with slightly more modern propulsion in the twin Cat diesels. There was a peculiar characteristic that if the one engine was put astern while moving forward the ship would fairly quickly turn in the opposite direction. Normally twin engine boats will turn towards the direction of the reversing engine, but not the Bounty.

We were entering Circular Quay with a tail wind making a turn to come port side along the oversea passenger terminal (pink in the image below). The captain called for starboard helm and reverse on the starboard engine. The ship started to turn to starboard but then fairly quickly turned to port. The captain put both engines in neutral then tried the same maneuver again, with the same result. All the while the wind is pushing us down on the ferry terminal. A couple of attempts later and we ended up broad side along the ferry terminal, blocking about 4 of the docks (shown in red below).

I ended up jumping in the rib and pulling the bow off the docks enough for us to power out and we managed to come along side the passenger terminal dock with no further chaos.

Yes, there was a very good audience complete with ferries waiting to dock.

Circular Quay.jpg
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Apr 8, 2011
Hunter 36 Deale, MD
I was singlehanding under auxiliary on a windless day back from an overnight in the Choptank River. Beautiful clear day, and as I entered some shallow water I started to encounter the expected crab pots at that time of year. I was trying to take care of some things so I let the autopilot steer while I kept a somewhat close eye on our course vs the crab pot floats. One set of floats was particularly well marked (which is not always the case) with a bigger than normal float in high visibility orange, but I judged it would pass to port safely. As I bent to another task I waited too long to check the course progress and next thing I knew I heard the "thonk" of that big float smacking the port side of the boat. Clearly the autopilot was slow on a course correction and I missed it. I immediately put the transmission in neutral and began hoping it would just pass harmlessly astern. But no such luck. As the boat coasted to a stop no float appeared until it popped up off the stern, clearly somehow attached to my slowly coasting boat.

Noticing a working crab boat nearby I waved for him to come over, wanting to give him the option to make the call on how to proceed before cutting the line as a last resort. These guys, after all, make their living out of these crab pots. As the, shall we say, very experienced gentleman who I presumed to be the owner of the pot got close I pointed to the buoy and asked if it was his string. He shook his head and pointed to another crab boat working almost a mile away and indicated that was the owner.

And then he said, with all the gravity of an elder schooling an errant child, "You did see that big buoy, didn't you?". To which I sheepishly said "Yes, I did." At which point he again shook his head disapprovingly and said "Son, you just shouldn't be out here.", and then putted away to continue working his pots. I felt about 3" tall, with nothing to say.

Fortunately I was able to slowly back off the pot and it popped free, just being caught around the leading edge of the keel, so no harm done to crab pots or boat. I'm a little more careful about clearing crab pots after that incident. Lesson relearned.


May 21, 2004
Jeanneau Sun Odyssey 409 Mt. Sinai, NY

Unfortunately I have too many embarrassing moments to tell in one sitting. Here is one of my better(?) ones.

My family and cruised to NY City and stayed at the 79th boat basin. The place was run down but in a great location. We were there for a few days and had a great time. It was time to depart so everyone was aboard, engine running, etc. We were in a slip: bow in, port tie, with the current from the stern. I explain to my wife how were going to depart:
She goes forward and releases the bow line
I will release the stern line
Boat in reverse.
Prop walk will pull the stern to starboard, away from the slip. I will reverse away from the slip, and back out of the marina.

So all goes well but once the boat got a little sideways to the slip, the fast current running down the hudson river took over and there was no way I could reverse and steer. We went sideways right into the side of the dock, hard enough to make a very loud BANG. I was sure I cracked the hull in two and expected to start sinking. After getting out of the marina I was relieved to see just a small crack in the rub rail.

I was pretty shaken up after that but calmed down later and enjoyed the (uneventful) rest of the trip home.

I now pay a lot more attention to fast currents when around a marina.

Mar 1, 2012
1961 Rhodes Meridian 25 Texas coast
I had just finished the build and launch of m y 35 foot trimaran. About the third time I took it away from the dock.LOt of current. Current caught me and put port ama up on top of dock coming back in- took about 6 guys lifting and shoving to get back off!!!!! Fortunately no damage except pride :)


Jul 13, 2020
Hunter 30T Neptune
hit the Belmar bridge, on a day sail with two other boats, checked the bridge height says 50, radioed two the two other boats what is the bridge height " chart says 50" well i say we are at mid tide I'm 50' from water line should be close from what I think I was taught bridge heights are supposed to be taken from high high tide. Guess the outcome!!!!!!!! expletives!!!!! fixed bridge buy has a draw right next to it radio explodes with " sailboat hit the bridge first two clear Capt of the sailboat that just hit the bridge, Capt. what is your plan? meanwhile there are about 30 boats in the inlet. fortunately no damage no other boats involved. felt like one of those YouTube videos... hell, I might be at least it wasn't a docking fail video of us crashing into other boats. figures had to get the tall rig.
Nov 30, 2015
Hunter 1978 H30 Cherubini, Treman Marina, Ithaca, NY
An older posting, but yet still living this one down from crew friends:

One hot and incredibly humid first evening in Roadtown, Tortola, aboard our bare boat charter we had just finished provisioning the boat in the dark. Donning my brand new, multi-functional Black Diamond LED headlamp, wrapped around my sweat soaked baseball cap, I decided to take a breather behind the starboard wheel. As I removed my baseball cap to wipe down my brow, forgetting I was wearing the headlamp, it sling shotted off my head, bounced off the sugar scoop transom and dropped into the 20 feet of questionable quality seawater at the pier. It remains to this day.

Fortunately, I remembered an identical headlamp I had also purchased for the Admiral. I found that in the luggage, placed it on my head, and repeated the exact same scenario not more than 30 minutes later. I was immediately demoted to captain dumb ass by the Admiral.

Tom J

Sep 30, 2008
Catalina 310 Quincy, MA
I still have the video my dock mate made of my seven attempts to back into my slip on a day when the wind and current opposed each other. I ended up stuck sideways across the front two pilings of my slip, and it was a case of "all hands on deck", literally, as the Admiral and I and our two guests grabbed pilings and pulled the boat into her slip.
Jul 13, 2010
Precision 23 Perry Hall,Baltimore County
Single handed, approaching the pier at the tiki bar, going to await the admiral arrive from her Sunday visit to her mom. I run forward with stern line in hand to greet the rapidly approaching floating pier. Boat bumps the pier, I trip going over the rail and hit the pier on a 3 point landing,almost wobbled overboard before a shaky stand up. Walked to usuall seat at tiki bar, bartender has refreshments ready,"Sure you want this?, that was pretty ugly!".. "Sure was,gimmee two" !