I guess my sailing stories are somewhat limited so can share them all in one shot. I started sailing in boy scouts at about the age of 14 and the sport nearly killed me. One day we were racing another boat on a small lake with heavy winds. Our mast snapped in half and instead of falling back away from the boat I was thrown forward and landed under the sail as it was capsizing. My life jacket got caught up with the spreaders and I was pulled under. I removed my life jacket, which took a good 15 seconds from the mess and floated to the surface, inhaling some water. After that, later in high school, progressed into catamaran racing on Lake Ontario, and then into university continued doing it well into the colder months, with full wet suits. For obvious reasons a cat doesn't turtle upside down all the way, but I recall we had a moment during one race in cold waters we couldn't right it back up because we were so numb. Myself and two other guys over 6 feet and built well, the water made us helpless despite the wet suits. After about 20 minutes we got enough strength to right the boat and continue, after attracting a sizable crowd on the shores.
Fast forward to the Bay Area about three years later. First exposure to larger boats and decided to take the ASA cert path. Enjoyed it, a lot. Here are a few stories:
1. I just left the (Richmond) marina with a group of friends and one spotted a buoy in the water. I was like ok, someone must have lost it. So I gave him the hooked pole and we sail towards it and pull it out. Well, what we didn't realize was there was a race going on (Lasers) and that was one of their way points. Surely enough we see the large fleet headed towards us and some guy yelling "what happened to our marker". Hence we crashed an entire race.
2. On a fine sunny afternoon, we were sitting at the marina restaurant for lunch, which overlooks the slips. There was some guy climbing the mast of his boat. He was replacing or installing something. His wife or girlfriend was below and for safety, he was tied to the halyard, which in turn was hooked to a winch. For those that don't sail, the winch has a small trigger near the pivot point to allow for locking in either direction. Needless to say, we heard what started like a small argument that escalated into yelling. I think if I was in his position I wouldn't do that because she had full control over that line. Well surely enough it reached the boiling point and she rambled off a few expletives, secured the line and left him dangling there on top of the mast. Everyone in the restaurant stood up and saw her head to the parking lot and take off in their car. Obviously he had no way of getting down, so we went down to the dock and "rescued" him.
3. On a typical sailing day, we would stop in Tiburon for lunch. One day I was skippering a Hunter 35. First of all, I'm not a fan of "wide butt" yachts. I prefer the narrow fast boats. We docked perfectly. And you need to, because about 100 people are watching you from the restaurant decks. Now typically I used to arrive at around noon but this time it was closer to mid afternoon. Left the yacht, went to get food at the restaurant and came back. It was only our boat and a police boat docked in front of us. I asked my crew to untie the lines and I hit the throttle. What happened next was embarrassing. The boat did a violent 90 degree turn into the dock and the water around it turned from clear to mud. The four police officers were watching me with arms on their hips. At first I thought this is not suppose to happen, then some dude on the docks yelled out and asked if I hit the side thrusters accidentally. I WISH I had side thrusters. Of course, I glanced on my depth gauge and turned quite red. It read 0. The SF bay has two tides during the day. I forgot to check the depth at low tide and account for the length of my keel.
4. I invited my friend from Hawaii over for a day of sailing since she's never been before. For the non-sailors, the "slot" is an area of the SF bay roughly defined by the triangle from Sausalito, Alcatraz and the southern end of the GG Bridge. It's racing paradise with winds of about 18-24 knots on most days. Since it was only the two of us on a 40 ft boat, I put her to work on the jib. Lots of potential rope burn, turning and strength needed, then had her skipper the boat. We were heeling like crazy, so I told her not to be afraid, the boat will not tip over. Between the screams, pulling on ropes and constant trimming, she said sailing was not what she had in mind. I asked her what she thought it meant. She said in her eyes she thought she would be laying on the fore deck in her bathing suit and sunhat like you see in J Crew clothing catalogs. Enough said. I guess it's the media's fault for selling sailing as something that rich people do if they don't play golf, hardly the case, because sailing attracts many different people from all walks of life. I don't consider sailing romantic. To me, if I'm not tired, muddy (due to anchor) and a bit bruised up from the labor, then it's not sailing. The good news is she slept very well that night and it was better than running a half marathon, at least physically.
5. My first knockdown was very close to Sausalito. This is the most severe thing a sailboat can experience whereby the wind is so strong that the sail touches the water, as it a 90 degree hit against the water. By design and due to laws of physics, even if a sailboat was to capsize, it will right itself back up within about a minute. However, all your stuff below, especially the kitchen, will be a mess. There was strong winds and severe clouds that day over the pacific rolling over the north end of the GG Bridge. We lost wind, so I pulled in the main to maintain speed and then without much warning, we got hit with wind sheer. The instruments registered it at 70 knots! We were both tied in but my girlfriend had a lot of slack so I let go of everything as she went flying from the starboard to port side of the boat, hitting the lifelines, then me pulling her back in with one hand by the first thing I was able to grab, which was the back of her life jacket. Luckily she only weighed 98 lbs and was small.
6. I had a coworker over from Tokyo and took him out on a brand new Beneteau 32. We were under the Bay Bridge with him at the helm. During that time they just started building the new bridge so there was a lot of construction equipment on barges. The current in the bay is very strong. Strong enough that under some conditions, it's capable of taking a boat like that and twisting it 180 degrees. I was below deck making lunch for us when I sensed the boat twist, a scream in Japanese and then frantic help calls. Well, after the boat did what the currents wanted it to do, we were within about 30 seconds of striking sideways into a metal construction barge. Although not recommended under normal circumstances, I powered up the motor at full throttle and trimmed the trail as close to the wind as I could get it. We missed a potential $240K mistake by literally 50 feet.
7. Within two weeks of being certified to sail the 40+ yachts, we were somewhere south of the Richmond Bridge in open water. Saw a tugboat heading towards us. Let him pass, then tacked to sail just behind him. The captain appeared on the deck, stared at me and yelled out "you've got to be f****** sh***** me!". Now, one thing about tug boats. About half the time, they are not pushing something, but pulling it. It this case it was a barge, about 1/4 mile behind it. My first instinct was crap ... barge + tugboat = towline ... heavy sailing yacht = deep keel ... deep keel + towline = disaster. I made an emergency tack and barely cleared it.
Finally , for ASA 103 and 104 Tony Johnson was my instructor. He was fun although quite hardcore. Perfect trimming to maximize speed or points off type guy. Looks like he since had written a book about his experiences aboard a sailboat him and his friend used to circumnavigate the globe. He told me the only nuisances they experienced were monkeys trying to steal food from their boat on the remote islands and some pirate activity off the coast of Thailand. And a hole they developed in the hull off the coast of Africa. The lady you see in the photo is his fourth wife. She would meet them at predetermined ports but didn't sail. I asked him given that he was on his fourth marriage, if that was maybe a sign to give up. He said "never, I love the institution and I love women, as much as I love sailing".
http://www.marinij.com/ci_23629038/marin-snapshot-drummer-tony-johnsons-around-world-sailing
http://www.ussmaverick.net/
On a side note, I've skippered many different yachts, from 25 to a 44. My favorite yacht? Pacific Seacraft Crealock 37, by far. Mind you never tried the custom high end ones like Baltic or Nautor's Swan.