I,too am a fan of sailboats. I currently have a 17'4" Compac Suncat that I tow when I know I have a good boat launch near my destination. Other times I go to places you've described (Rangey Lakes,Grand Lake,etc in Maine)and I bring my 14' inflatable Hobie Mirage tandem kayak with pedal drive and a sail kit.It is a wonderful little sailboat and a great flat water kayak. It is easy to put 10's of miles on in a day without becoming exhausted. The tandem Mirage drives act as center boards,while the wide (3+') beam and small sail area make for a very little heel. Since you are essentially sitting at the water line,you become the boats ballast. We carry it on a flat rack on our trailer hitch.
My wife and I have always felt perfectly safe in our little boat,except for our encounter in Pleasant Bay,Chatham,Ma with a great white. Fortunately,it was a very brief encounter.