Originally Posted by mattt
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.
The printed checklist was amazingly helpful with my first sailboat, a 17 foot Whip (bySailMFG), and it's good for when you sail with people, since they may not know what to do intuitively, so even when you have the list in your head, it's good basic info for them and a backup for you.
I lower the sails a little differently when I'm alone, depending on the wind. Generally, I heave to so that I'm basically at rest, and don't have to steer. I then lower the main, then furl the jib, and I'm on my way. It really is easy.
I also second raising the mast and sails at home when there is little wind. That's how I figured out a couple of steps when raising the mast of our 17 footer that made doing it at the boat launch much more efficient.