Originally Posted by Lemonshirt
Did I mention that I forgot to lower the swing keel before raising the sail?! (I put that on my mental check list for next time)
Nothing beats a printed, paper check list. Update it every time you learn a lesson, print 20 copies, and stuff them in your cabin binder.
Like most folks here, I like keeping the engine on while hoisting the main (and keep the bow in the wind) so that if your sails have trouble your engine is still ready to go.
I also prefer to hoist the main, fall off to port so you are on a starboard tack and kill the engine. Now you are the stand-on vessel for most situations. THEN, when you are reaching, unfurl the jib. That way it doesn't whip around in the wind. The sound of a luffing jib makes people feel tense.
Perform the same steps in reverse to go back to the marina, or wherever you need to go. Take in the jib while sailing (avoids luffing) but you'll need someone to keep tension and let out the working jib sheet while you furl. Strike up the engine, point to irons and douse the main.
I've had a few really bad days myself, as a relative n00b, but I'm having fewer and fewer these days as I learn from my mistakes.
Have fun and happy sailing!