I got in a shakedown sail in my new to me (free) Flying Scott. It was blowing pretty good, 15-20 with bigger gusts. My wife has sailed like twice before and my son 3-4 times since he can remember. It was a bit too much for them and I should have waited until a nicer day but I consulted a good friend and he said "when in doubt, sail."
I haven't piloted a sailboat in about 9 years but everything went well. We were really screaming along, we passed everything in the bay.
I would have reefed down but none of the 3 mains that the boat came with have a reef point so we dipped the rail quite a bit. I was shocked to learn that under pressure I still remember the names of everything, but it doesn't really help if your crew doesn't know the names as well.
I sounded like Don Vito sometimes trying to think of another name for a halyard.
AHH DDDUUUH Duh the DUHH Duhh line there on the DH DUH mast thingy there.