You might check with some of the larger charter companies in Annapolis. But I'm not sure if they will be quite as turnkey as you might hope -- maybe.
Another option would be to search on-line for a private party that charters their family boat. This might give you a better chance of getting all the goodies along with the boat.
I would think that a decently equipped boat from a major charter company would still be a good way to introduce your family to Chesapeake sailing. Make sure the boat has a good bimini system and a dinghy. Then choose a fun itinerary and it should be a memorable experience. Good luck.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT