Have you ever felt like you can't trust your boat, and it scarred the crap out of you?
On Saturday, my wife, my mother, and I took a sail as well as got some errands done such as pump out the holding tanks and fill up with diesel. We decided to have a leisurely dinner at the yacht club before heading back to our home port in the dark.
On the way back, my Mom and I reminisced about our life sailing with my father. As a kid, I figured there was some unwritten rule that said:
"Sailboat engines will always fail at the worst times" and it's corollary, "You will never return from a daysail before Midnight".
Just a few examples:
In a SJ21 with a Seagull outboard, we were returning from watching fireworks in Commencement Bay and after the show headed back to our marina in Day Island. Part way down the Narrows, the Seagull quit (as it was wont to do frequently). We had little wind, and were running against a 3-4 knot tidal current. It had been a very hot day, and quickly turned into a very cold and very long night. We made it back to our dock around 4:00am, docking under sail (easy to do with the dinghy-like handling of the SJ21.
Sneaking through a very narrow channel against the current to get into Prevost Harbor on Stuart Island (my Dad didn't want to go around Satellite Island to the decent channel) in our SJ24, the Evinrude outboard literally blew the cover right off the engine. We suddenly had no power, no sails up, and were in a channel about 30 yards wide with rocks on either side. We got the sails up quickly and were able to tack through the channel and drop anchor (to the great entertainment of the other boats in the anchorage).
My Dad took my wife and sister-in-law out for a day sail in Commencement Bay in his Cal29. Great day, great sail, the outboard quit. Again, the wind died, the current was against them, and they sailed back into the marina at 2:00am.
Growing up, this type of thing happened all the time. Mostly because my Dad never saw an old sailboat or old outboard that he didn't like. Everything either was a "bargain" or had "potential". Hence, I always thought that sailing was the process of dealing with one minor crisis after another. That doesn't even consider racing, where boat and gear were pushed to the limit during the winter season.
So, I have two suggestions. First, fix and maintain your equipment so you have confidence in it's performance. Second, mentally prepare for problems because they will occur.