We were out on Lake Ontario last summer in 6'-8' waves with short wavelength..not fun sailing..not really difficult, just slow and a lot of work..We were going straight upwind about 20 miles. How far is it? I wouldn't want to get caught out there at night. I would probably drive around if what you are talking about is crossing the lake. And I definitely wouldn't do it alone. All it takes is one little thing and you are in a lot of trouble. There are over 6000 ships on the bottom of the great lakes!