I take her out for her first sail on Wednesday. Since I don't actually know how to sail, I checked out Lattitude38 for someone wanting to crew with lots of sailing experience. We'll see how it goes. Wednesday will be mostly a rig check and introduction, so to speak. But am glad I'm getting the chance to start sailing her. :-)
Also, at this point, again, since I'm a novice, I plan to stick to the estuary, where winds are fairly light. It's a large enough area for me to get to know my way around the boat without having to worry about currents, or high winds, for that matter. SF bay is notorious for both.
And finally, I've already taken time getting to know how my running rigging is set up. She's set up with the main halyard (of course), two jib halyards, and a genoa halyard. And everything is running aft for single handing.
As for doing this with a little one? Awesome. Hopefully you've checked out the cruising and sailing with children forum
. We have a couple of families at our marina. They're just passing through. The kids are older (teens) and being home schooled. Imo, getting kids acquainted with sailing early is a pretty neat idea. :-)