With the weather turning colder by the day, I've been wondering....

In the winter months, how common is it to overnight in a place that is relatively mild? Not necessarily tropical, but lets say somewhere with average temps in the 50's or higher?

Furthermore, how common are trips to the Bahamas and/or Caribbean during the winter?

Correct me if I'm wrong, but I presume the frequency of this is not strongly correlated to where one is based.

Thank in advance