January is sort of mid season. Christmas and New Years are high season, not because of conditions but because kids are out of school and working folks can take a longer trip using fewer vacation days. There are fewer visitors in January, then things ramp up in February, through April. That, and the fact that the islands are still in recovery mode, means things are not over-run in January. Of course some resorts have not yet re-opened, so the remaining ones may be busier than they would otherwise have been.

The Christmas winds may still be blowing in January, which makes some anchorages more comfortable than others. Your captain should know the best ones. You might want to look at the Bee Line on Little Jost, Guana, Leverick and Anegada, for starters.