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Whoops! Mistakes Made on the Water

Here’s a personal question for you, Latitude Nation: What are some notable mistakes, mishaps or misfortunes that you’ve had while sailing or messing about with boats? What was silly and ridiculous? What was serious and sobering? What mistakes have led to demonstrably improved seamanship?

What mistakes are legendary to you?

Are you a trial-and-error type sailor and learner with an “If it’s gonna happen, it’s gonna happen out there” attitude? Or are you a meticulous planner?

What does the comparison of mistakes look like between these personality types?

Are we calling this a mistake? Or an inevitability? Are we calling it gusto and valor? Are we calling it an important, courageous step toward high-level skill? Call it what you will. Thirty seconds later, this crew had their kite flying smartly and were steaming downwind.
© 2025 Latitude 38 Media LLC / Tim Henry

One of my smaller, lower-budget “duh” moments on a boat was about seven years ago while anchored at China Camp. I threw a lifejacket into the water with a long line attached … except that the long line wasn’t attached.

I can’t remember exactly what my faux pas was — I think I had led the rope through the lifejacket and intended to tie a bowline, but hadn’t yet tied the knot when I threw it into the water. I clearly remember the lifejacket floating helplessly away, astonished that I’d made such a ridiculous mistake. I thought about jumping in after it, but then I would have had to scramble-strip and deal with the gnarly current. The “swimming line” was necessary because the current ripped through China Camp, and we’d been shocked during previous anchorings at how difficult it was just to swim in place with the boat, let alone swim back to it.

So I watched the poor lifejacket drift away to its slow demise somewhere along the marshy shores of San Pablo Bay. My biggest concern was the vest degrading in the sun and saltwater for years, marring the otherwise clean shores of the Bay. The thought stuck in my mind like a thorn for months.

The same caption from the previous photo could be applied here. This ripped spinnaker was the result of some serious moxie from a singlehanded sailor during the 2018 Westpoint Regatta.
© 2025 Latitude 38 Media LLC / Tim Henry

Your turn, Latitude Nation. Let’s hear about all of those “whoopsie” moments both small and large. All mistakes are welcome, but it’s those mistakes that made you a better sailor that can be particularly informative to the rest of us.

Please comment below, or email us here (especially if you have pictures).

 

7 Comments

  1. Ernie Galvan 6 hours ago

    So very many of these. July 1999. My now-wife, then girlfriend and I capsize a Lido 14 near Ashby Shoal on a big summer slot afternoon. We right it, it goes over, etc. I decide to anchor to keep the bow upwind. I grab the anchor and forget entirely to untangle the rode. Instead I just drop the whole mess in the water, through the tangle of swirling sheets. Now, we’re not anchored and our circumstances are worsened by a fouled anchor nowhere near the bottom and holding our sheets in the water. Fun day.

  2. Steve 6 hours ago

    One time years ago when coming out from behind Angel towards TI when we entered the slot the breeze was more wind than we expected. Suddenly the boom is in the water to port and the rail was buried. When we finally stood up the knot meter was registering 14 knots. With some fear and trepidation was released the main sheet to de power the boat and settled into a calm 10 knots. Till we arrived shortly behind TI where we were able to clean ourselves and regroup! WOW!! Quite a thrill to live through.

  3. Steve Edwards 6 hours ago

    Sailing a 16-foot Y-Flyer on the Mississippi River above Alton Dam, 1969, my second date with a high school senior. Her first ride in a sailboat. I explain what happens during a jibe. Five minutes later, we begin to jibe. She’s not ducking her head. I raise my voice, “Nancy, duck!!” She does, “Whoosh” goes the boom and mainsail, then I stand to change sides. She stands, facing me, “My name’s not Nancy!!” With one hand, she tips me head-over heals over the stern and into the drink. The boat meandered, happily reaching me within 5 minutes.
    No fatalities, no lost limbs,

  4. Vince Casalaina 6 hours ago

    Summer 1995 – Snipe Nationals – RYC. It was a typical summer day about half way between the breakwater entrance and the Berkeley Circle – winds in the high teens, ebb tide, lots of chop. My crew and I were sailing the best race I’d ever driven in a Nationals. On the reach to the gybe mark, we had passed one of the best sailors in our local fleet and were setting up to gybe. I told my crew I was waiting for a flat spot to gybe, looked over my shoulder, pulled on the tiller and yelled “jybing”. As the boom comes crashing over, she’s looking up at me from the low side as the boat lays down. Things get worse as the mast sticks in the mud. We can’t get the boat up. We both get a little hypothermic and ask the crash boat to take us in. By the time we warm up and get back out on the course, the daggerboard is gone (retaining line snapped) and the mast is bent in two directions beyond redemption. What did I learn? Make sure you get a “ready” call from your crew before executing a maneuver. You are more likely to get the maneuver to happen cleanly and that almost always saves you money for sail and/or boat repairs.

  5. Greg Clausen 6 hours ago

    One of my first mistakes sailing was owning a hobby cat that flipped over, which was not the problem because that’s what they do, but I was not wearing a life jacket and the only way I put a lifejacket on was the one on the boat came off and started to float away when the boat was flipped. When I managed to flip the boat back over, Augusta wind caught it, and the boat sailed off by itself and leaving me in the water in the middle of a large lake where I would’ve drowned if I was not wearing the life jacket that came off after that, I vote to always wear a life jacket whenever I go sailing and I still do to this very day with many thousand miles of ocean sailing under my belt

  6. Richard vonEhrenkrook 6 hours ago

    We were doing the BAMA Double-Handed Farallones. Paul Sutchek and I had rockpiled many times in the Can, but this was a smoker. The wind, out of 240 degrees, was blowing the top layer of water much faster than usual at the Northwest corner of Maintop, and it took three tries to stay north of my safe waypoint. We were taking major green water over the bow, and I knew some pumping was in my future, once we made the corner. We did, adding many minutes to our time on course, but blasted down the west side on a Starboard beam reach, and licked our wounds. A beer apiece to dilute the salt water, and as we approached the southwest corner, I was wary of a hard jibe in the steady 25 knots; we were a long way out, if anything broke. I called for a “chicken jibe”, and Paul agreed. But, when we went into the tack, I had not taken up enough mainsheet, and in the inevitable flogging, the sheet wrapped twice, and seized, around the boom end. Now, we were headed, at speed, right back into the island, and I couldn’t bring the boom in enough to accelerate enough upwind to complete the tack. It took three tries, but we finally got around on Port, with Paul behind me, unwrapping the mainsheet, and set course for San Francisco, scared shitless and exhausted. Paul looked hypothermic, but refused to go below, so I gave him the helm (the wind was too west to set the kite), and went below to pump water and put on dry layers, figuring when he was ready to go below, it would be sorted, and I would be strong enough to TCB Solo on deck. We won our Division, and thrashed the StFrancis YC with our wet gear when we dropped by the Race Deck after finishing. Moral was: Take up the freaking mainsheet on a chicken jibe!!

  7. Rich Brazil 3 hours ago

    Tally Ho had an electric headsail furler, a very strong one indeed. So strong, that unbeknownst to me, I created a halyard warp and snapped the jib halyard at the masthead while furling. Out the Golden Gate we went, hard on the wind. We were having a grand time! The partially furled jib held in place only by the friction of several wraps.
    About a half mile out we decided to head back to SF and fell off. Easing out the main, unfurling and easing the jib for a nice reach under the Gate. Only one problem, the jib fell in the water!

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