We don't have much criteria - just a looking for a nice home, maybe on the water or with a view and reasonable taxes. Access to good sailing is important but that doesn't rule out much on coastal Maine as far as we can tell...
Here is my 2 cents worth:
Buy a home on the Sheepscott River in North Edgecomb Maine.
That river leads to the open ocean fairly quickly, is generally 90 feet deep, is just outside of Wiscasset and just North of Boothbay Harbor.
Beautiful area, many homes have their own docks. So, you could dock your boat there, and take her out in the winter.