I'll be the contrarian: Take em all at once. You have no one to blame but yourself at this point.
You have to know the harbor and the weather. Protected water. Set the safety rules (PFD's etc.) you think are prudent.
We often give the 'harbor tour' to friends and visitors. I've never taken that many but 8 or 9, maybe a few times. I'd never sail with a large group. Even though we can seat cheek to cheek, 8 in the cockpit, I couldn't sail the boat if I wanted being trapped by them all.
I'd motor only and if the conditions are perfect, I might unroll the genoa for a glide back to the docks. That alone is usually impressive enough for non-sailors.
We've taken a few photography classes out for a short trip (we have a photog. school in town). This was one our son was in. That would be him in the bosun chair (he grew up hanging in the rigging), taking the class photo.
The cool thing was, the class then took Young Tom's pic, sitting on deck, and photoshopped his image into the group - on deck. You wouldn't have known it by looking at the photo. Assume nothing.