The "Christmas Winds" are basically reinforced tradewinds, and usually kick up in late December (hence the name), but could occur any time during the
winter months. The trades normally blow from the easterly sector in the teens, but if the mid-Atlantic High gets well established, it will drive the winds up into the twenties or even low thirties (knots).
It can be predicted a few days in advance, but if you're chartering, you'll just have to make the best of what you get. The Sir Francis Drake Channel is relatively enclosed by the
BVI islands, so you don't get large, wind-driven waves there. So if the
Christmas Winds come when you're there, just reef down and enjoy the sailing!
Here's a good source for seven day wind/wave forecasts:
Windfinder-Beef Island, Tortola