Down here it really depends on how open the borders are. I don't want to leave Grenada for a country that will impose another quarantine on us and even if they (SVG for instance) don't, I don't want to have to go through it here again, either.
However, it is still my opinion that the only reason one should leave home is for essential reasons, and I don't see sailing or any other pleasurable pastime fitting that criteria.
Germany is already showing an increase in new cases since the easing of the lockdown there and it seems foolish to do the same here. The US should wait and see how the easing works out elsewhere before doing it here. But of course, our politicians are so worried about re-election that they will put hundreds of thousands at risk just to seem to look good.