It is my understanding that the winds start to die down as you approach the summer, but i do not know this as fact. there is a weather site that provides historical wind data for last year and beyond, and this would be of help.
When went with a 322 Beneteau during Christmas to New Years this year, we were told by the Moorings to circumnavigate Tortola clockwise . . . the winds, for the most part, were coming straight down the channel. However, when we were on the back side of Tortola (the Jost van Dyke side), the winds seemed to be coming straight at us, too, when we attempted to head north to Trellis. While down there, we met some sailors who typically go counterclockwise and others who told us that they always go clockwise. This was the first time we bareboated, and I am a new sailor, just learned this summer, and the waves on the Tortola back side were high for us . . . about 5 to 7' or so. Some appeared higher.
The crowds should be a lot less in April, too. During the time we went, we tried to be at a harbor no later than 1:00 to get a mooring. Depending on the harbor, some moorings were still available until around 4;00.
I am planning on going back this summer.