I'd go on the Chesapeake! You couldn't have 3 fly rods going at once, but you could have one at each end of the boat with a spin rod in the middle. I'll be doing exactly that on the 11th going out of Kent Narrows. This is my favorite time of the year to be on the Bay!
The Gunpowder is certainly another option for 3 guys to stay relatively close. It's hard for 3 to fish the other two waters you mention.