Certainly every skipper, captain, master... is different. I can only imagine the eyes of the amateur charter boat once a year skippers who frequent TTOL having a crew member hop on the boat and handing him or her an itinerary(boat path) for a week. I suspect any professional mariner will not enjoy the __________________.... The reality is the better paid skippers will first try to make sure there are no surprises, anxiety, risk, worries, painted into a corner failures on his watch. I would review with the hired professional skipper what you most enjoyed on the last trip, what you want to avoid on this trip, and the things you must do like meet your sister. Then let the hired skipper plan the navigation for the week. In my opinion the biggest error many make is trying to "hit" or punch the list with too many spots or must say they were there events or locations. Since it has not come up. With all those kids I would try to make sure you have at least one stand up paddle board and one two man kayak(the bigger and more stable the better) on the boat. We have packed as many as 15 kids on a boat and found as long as we do not rush any of the Moms all goes well. In many cases long late leisurely big lunches ashore with simple dinner on the boat can work well too. No hassles, no hurry, no agenda. The boat moves downwind when everyone is ready for the boat to move again.