I'm a new member here and you've been most helpful. I figured I might tell you about my initial experiences with sailing. The wife and I picked up a 14' Bluejay right after we were married. I had no experience with sailing at all, didn't know the first thing about it. I picked up a book on it, got all the registrations done and a couple of friends, Bill & Lisa, took us sailing on a local lake.
It was an interesting day. At the end of it we pulled up to the ramp, I went and got the car/trailer and backed it up to haul the boat out. There was a line of cars there waiting to launch their boats (all motorboats) and I figured I'd be a good doobie and get out of their way, so as soon as Bill indicated the boat was on the trailer I drove the car out of the small lot, figuring I'd take all the rigging down after I pulled it onto the street. As I pulled onto the street there was this loud crack and the car jumped. I pulled to the side and got out. Lisa was still in the boat! That surprised me. She had this death grip on the mast. I asked her "What was that noise?". Her response was simply to turn her gaze from me up to the mast and I followed. My mast was about 5 feet shorter! The top 5 feet was hanging down by the rail. I hit the phone lines.
Lesson: Don't hurry.
After I fixed the mast we were ready to go again. The boat had come with a spinnaker but the mast wasn't set up for it. So I put a pulley on the front figuring to use it to raise the spinnaker. We went sailing again and we got that spinnaker to work. Except that the winds were rather changing in direction that day and not being that experienced I figured it better to only have to deal with one sail, so I put the mainsail in the middle and tightened down on it's sheet. Now I only had to deal with the spinnaker. About halfway across the lake I heard this loud crack (again). I looked behind me and the rear deck was practically ripped off! It was only holding on by 3 screws and had been ripped off by the mainsail sheet. I jumped on top of it, immediately let the main sheet loose and sailed it right back to the ramp. The mainsail sheet went through pulleys on this deck, when I put the mainsail amidships it took on the role of a stay. Obviously, it didn't stand that role well. So I fixed the boat again.
Lesson: Do not make any modifications to a boat without researching it REAL well.
Some time later, with a bit more experience we had the opportunity to go sailing down at the Cape (Hyannisport, Cape Cod, MA). We had a great time the first day out, it was such a nice day we figured we'd try taking it out to the ocean for just a bit. We're sailing nicely out the inlet when I hear this really loud horn. I look behind me and there's this ocean going ferry about 50 yards behind me and coming fast. WHOA!!! I got the heck out of its way and it roared past (well, you know what I mean...), he speeded up after I got out of his way. Then there was the wake he created! It seemed about 4 feet high and looked like a high frequency sine wave. Suddenly I had visions of the boat rolling so I turned into the waves, figuring I take them head on. I hit the first one and the bow went up into the air, then it came down right on top of the crest of the next wave. There was daylight under the boat. I heard a loud CRACK! DAMN! I was really getting to hate hearing that sound on my small wooden boat. Really. We started taking water immediately around the centerboard housing. I limped back to the ramp, the wife bailing, and hauled it out. As the boat cleared the water, water poured out the middle of the keel, I had a broken keel.
Lesson: Do not get in the way of ocean going ferries and don't take high frequency waves head on, take them at a bit of an angle!
Well, I got that fixed too and we had a ball with the boat after that. But a few years into the marriage the kids started to arrive and the boat sat unused so we eventually sold it.
But we sure learned a lot with that boat.