I have lost the typical stuff: cell phones, hats, seat cushions, winch parts, etc. One of the phones was a blackberry that my work provided. I called the help desk because I 'lost' the phone the service person said they would send a 'kill' signal so no one could use the phone. I explained that they didn't need to do that because I doubted the fish would be using the phone.
The one thing I lost that hurt the most was an expensive watch.
Someone else lost it, I found it (thought I had a record *something* at the end of my line):
one of those folding/collapsing metal-tube & cloth chairlike things. Cleaned up pretty nice, gave it my sister for her porch.
I will never forget dropping my pocket knife off the dock when I was a kid. Probably about 12 or 13. It was a Boy Scout logo folding pocket knife. By today's standard, it was junk. The blade did not lock open, so it was probably dangerous too. But I carried it everywhere with me, even to school, which I'm sure would be illegal today.
It was the first moment I recall feeling completely helpless and subject to a life sentence for my mistake. I still recall where I was and who was there. I even recall the explanation from my Father that the bottom was soft mud and murky, so diving for it was futile. I was crushed.
To this day, I keep floating fobs with small carabiners on them in the car to attach to keys when I'm at the marina.
I saw this skipper of the boat across the dock from us drop something in the water a couple of weeks back. Not sure what it was, but judging by the swearing it must have been something important. Anyway, with very little hesitation one of his crew dived in and retrieved it...and the water was bloody freezing. I was impressed, he didn't hang about, shirt off, straight in, and 30 seconds later was back on the boat being handed a towel. Not sure I'd have been so keen.
We just finished our first season with a boat. I was out with my stepfather (who taught me how to sail when I was a kid) and the winch handle slipped out of his hand. I wish I had a camera at the exact moment it happened. The look on his face was priceless - within a split second it changed from surprise, to shock, to chagrin.
I started laughing my ass off and told him not to worry, went down below and grabbed the spare. The next day I discovered how expensive winch handles were. Glad I didn't know it at the time - forced cheerfulness wouldn't have been nearly as much fun.
Besides all of the pairs of sunglasses, and a couple dozen hats, my worst loss was my custom stainless steel boarding ladder, that was part of my stern pulpit, that I unpinned from it's hinges while sailing along, so that we could more easily pee off the back transom platform, and managed to slip and drop it in the drink. I priced a new one at $450 before I decided to make do with a cheaper model.
Wife's glasses when she was bent over the life line, she had no spares and we were on a 10 day cruise...road trip. And a 12' serf casting fishing pole that was on the deck inside the stanchions, went over when a random micro burst broached my boat. It was a calm day under 4 knots wind, had full sails up and tight...and wham, down and right back up.
Ever notice how when you drop something on deck, no matter where you drop it, it bounces overboard?
To get the battens out of the main, you need to remove a small screw from the batt slides. The screw size and positioning was clearly designed by an engineer who was trying to make me crazy. Every year, we drop one on deck, first there's the ping as it bounces on deck, then the plop as it hits the water.
On one of our previous boats we had a sliding car on the boom for a in mast hood furl. It decided to explode one day raining ball bearings on the crew. Yep, that same ping then plop sound heard maybe 100 times in a matter of seconds.
Several years ago we participated in the season opening regatta hosted by our yacht club. The first race was on a pretty crappy day; cold, raining, and blowing pretty well. Most yachts started however, including one sailed by a husband/wife and one crew team. There were several crash and burns in the course of the first and second legs and a number of boats withdrew. At one point after rounding the 3rd mark we heard the wife of the husband/wife team notify the committee boat that they were disabled and withdrawing (DNF).
"Is anyone injured?" inquired the Committee Boat;
"No" responded the wife, "but I've dropped both our winch handles overboard so please check on me when we get back to the Club!"
We lost our stainless steel boarding ladder too. It took me a week to summon the courage to dive for it the cold water. Submersed a phone when I tried to soar the four feet to the pier as the boat was frifting off it. I did manage to cover 4 feet one inch though but couldn't find my balance using just my to big toes.
I've lost the usual, lots of sunglasses, a fishing pole, a batten, multiple lifeline cup holders, a hat, some small tools. Maybe the most heart wrenching was losing a good German dark beer over the side. There are few things better than a good dunkel and I treasure every one.