Originally Posted by sailingdog
This isn't to say that you should stick to fair winds and blue skies only, but that you should take the boat out in different conditions to get an idea of how she responds under various weather conditions and with different amounts of sail.
Unfortunately, most boats are different enough that this kind of learning is pretty boat specific.
We've been doing pretty well at being more than "fair weather sailors." We've been out in reefed and rain situations more than once on a range of boats, and we feel the harder conditions are becoming less of a concern and more of an opportunity. The only thing that's bothersome at the moment is that our Columbia has an abnormally high current, cross-wise to our slip, making docking and general sailing less fun than normal.
I've been thinking about crewing and other learning opps this week, and I've found out more about the local cruising trips offered by the sailing clubs and organizations. Right after our week-long charter in the San Juans, we might join a one-week cruise to Astoria and back on the Columbia, to learn more from the seasoned cruisers who sail much of the year in varying conditions and have a lot of local knowledge. Rafting up and learning more about their years of crusing sounds like a great experience.
Your note about boat-specific knowledge is also true, but it's kind of surprising how many opportunities there are once one knows the local sailing community a bit better. In the past week, I've read about crewing opportunities in the Sound and off-shore as people are moving their larger sailboats for the season and are looking for help. Both my wife and I would like to do this in the future, as well as do some crewing for racing. The opportunities are pretty amazing, and each is an investment.