I have done exactly that and with newbies on board. The day we departed from TMM there was no wind and so we motored direct to anegada. For the record, we had done a sleep aboard.

We had no issues with this leg.

Had there been 15 knots of wind, would I have done it. Not a chance. It becomes a long slog to windward.

Many head to North sound on the first night. That sounds like a similar challenge as getting to anegada.

So, it really depends on how early you get off the dock and the weather.