In my childhood here in N. FL, I spent as much time in a canoe as I did
on a bicycle. It was a Grumman 18' that was nearly indestructible
until it got under a log on the Suwanee in flood stage. A little TIG
welding and its as good as new, now 43 yrs old it is in my back yard
ready to use. We would fill it with kids, (I have 8 siblings), take it
out into the water and tip it over on purpose and play in it. As kids,
we could never figure out why this always got the Marine Patrol so
excited.
The point is, around here, even in Winter, tipping over is often
welcome and rarely dangerous.
Another possibility for this sort of cruising is Pine Island Sound down
near Ft. Myers. I have not been there but it comes strongly
reccomended by friends.
From what I have seen, Canada has as much scenic value as most of the
US.
In South FL, you will see many Snow Birds, last year when I sailed into
the area south of Sarasota I thought I was in Wisconsin because all the
people there looked and talked like my in-laws from there. N. FL is
very different. From north of Clearwater along the coast to just east
of Panama City, you will see almost no tourists.