No travel to Canada is currently allowed either, whether across the US/Canada border or by overseas visitors, unless the visit qualifies as "essential" (which does not include tourism) or it is a necessary commercial or cargo activity. I don't see those restrictions being lifted anytime soon, unfortunately.

With SXM also closed, I would be stopped at the airport. We have booked for 5 weeks in SXM, starting mid-January 2021. I am an eternal optimist, but I honestly think that the chances of actually going are less than 50/50. It would be a combination of considerations, including the idea of being in an aircraft without the benefit of reduced passenger loads (physical distancing), an effective vaccine (unlikely that quickly) or an effective treatment (a possibility) and adequate testing (pre-screening).

Of course, it presumes that air travel restrictions have also been lifted. We are keeping our fingers crossed, but we may have to just move it to 2022.