We've been out sailing during those weeks the last four years. In 2015 and 2014 on our Beneteau 40 we had 25kt winds and gust over 35kts with a north swell.

In 2014 we attempted sailing from Norman to North Sound and had to change our plans - sailing upwind fully reefed was not going to happen. We did have a nice downwind sail to Jost Van Dyke instead, making better than 9 kts. The second week we had almost no wind or swell and motored from Coral Bay to North Sound on the south side. Weather matters.

In 2015 we were ready for weather and Plan B was to stick to sheltered anchorages and limit upwind sailing. We had two weeks of a hard blow and did not make North Sound or Anegada. Could we have? With a lot of uncomfortable motoring we could have made North Sound. Anegada and onward to Jost would have been a reach and would have been fun.

Leinster Bay is usually a good anchorage during Christmas winds and a north swell. If you get one of the inner moorings you'll be better protected. But, the outer moorings have AT&T coverage, if that is important to you.

Spending the night in the Caneel Bay anchorage is not something I want to do again in a monohull. Ferries wake you from 5AM to 1AM and its exposed to the north swell. I would recommend spending the night at Christmas Cove, Water Island or Brewers Bay the night before you return the boat.

We'll be out again for two weeks in January. As hard as it can blow, the positive side is that there are fewer boats out and its cooler than the summer low season.

Cheers, RickG