Originally Posted by mazzy
which three choices in subject would be best?  Ease of sailing,  picturesque and  uncrowded anchorages are top priorities.
I have sailed the Chesapeake and Maine: no experience on the lake. While Maine may take the honors in your 2nd category - the Chesapeake is a clear winner of the other two.
I found the lobster pots maddening! Others are more apologetic. Current and rocks are part of the Maine experience. On the Chesapeake the tidal current is almost inconsequential and the bottom is generally soft, forgiving mud.
In terms of uncrowded anchorages unless you are able to quickly become an expert on Maine's (generally unpublished) possibilities, you will definitely find the Chesapeake superior. And if you want to find an occasional transient slip, the Chesapeake wins again. To avoid the "18-M other boats" don't
charter in the north bay!
Fog can spoil the Maine adventure; heat and humidity the Chesapeake. For either you take the luck of the draw. Early September mitigates weather for the benefit of both Maine and Chesapeake.