Our winters are typically mild comparatively and boats just sit at the slips. We don't really have moorings for boats, pretty much all docks /marinas. There are a very few boats now, count on both hands, that have uh, otherwise homeless folks living on them anchored in the rivers. I've seen one or two in the Columbia, five or eight in the Willamette right in the heart of downtown Portland. Not much has been done about them...yet. But it's blue tarp city out there on the hook for those folks and I've heard some grumblings about them.
This isn't Florida in the winter but they seem to be hanging on and slowly multiplying....