I would suggest you don''t pass on Anguilla. We had a great time there on the North West side. We also loved St.Bart''s. Use the cove on the NW point. Anchor and hike over the ridge to the Ocean side. About 1.5 miles South you find the greatest beach you have ever seen and some ocean surf. Have a good time.
Go about halfway to St. Croix and bang a left. ''Course, it depends on the wind slant, and beating it into the trades can be a pain in the ass. Last March I did it in glassy seas from Necker Island - glassy BOTH WAYS. Can''t ever tell, I guess....KW
We sometimes go to Anegada and spend the night, maybe get a better crack at the port tack. Leaving earlier in the day and planning on at least 24 hours (which is long) is a good idea. Lets you go out and get into the rythm of getting the **** kicked out of you while you can see how everything looks. It usually calms down a little after dark....don''t be in a hurry and go only when it''s right. Schedules cause problems.