As someone who lives in the upper Midwest, I’d vote for Canada in September every time. After the kids go back to school, the weather should be perfect and the crowds hopefully less.
September is my very favorite month.
You couldn’t pay me to go to Mexico in prime hurricane season. Even if there is no hurricane in the area, it will be the hottest and most humid part of the year.
But then, I’m not much of a beach person so I’m thinking my opinion isn’t really worth anything