We always sail with at least 10 - my skipper husband always says, "The more, the merrier," and he'd say his wife has never met a boat too big. We've chartered a 50 Saba with 12, and in May we'll have 12 on a 52 Lagoon. Last year our crew of 15 sailed St. Vincent/Grenadines on two boats, but it was more work for me logistically as the trip food planner, and we sort of missed our comrades on the other boat. (We used to sail tandem monohulls in the Abacos 35 years ago which was a blast with 16-17, but then we always anchored and tied up together - a floating party.) When taking the larger cats, we've been able to rent a second dinghy which works out very well; in addition to more comfortable rides, they allow for much more flexibility for such a large crew. The skipper conducts a safety/informational briefing the night before heading out, although at this point we have very few, if any, newbies on board; most are salty sailors. I always set up a wiki that everyone can access for all of the trip info, including menus, packing and shopping lists and meal duties. We eat on shore for half of the lunches and dinners, as well as LOTS of beach bar drinks/apps etc., but we also bring down several styrofoam coolers full of prepared meals/convenience foods and boxed wine (hey, we're on a sailboat), which makes meal preps a breeze. And every trip is a treasure!!!