I'm with JD. I don't really think availability of accommodations is going to be a big deal whenever the island reopens, SO LONG AS you do not have to stay at one particular place. If you are totally fixed on staying at one particular place and it's relatively small, it may be tough to get a reservation. The other factors JD mentioned would seem to be the more limiting factors. We have often gone to SXM in Sept/Oct, but this year, with all the uncertainty around Corona, in addition to hurricane season, there is no way I would consider going in September for sure. October, maybe.