Thanks all. I would like to avoid at all costs bashing to weather for 24 hours. My original rationale to go to Anguilla is that we will be a crew of 2, I have pretty significant off shore experience but the admiral none so watches are going to be interesting. I'm thinking going directly to Guadeloupe is probably a 48 hour sail??
I could stop at St. Kitt's saving a few hours, but was down that way last year and moorings/anchorages seemed a bit tenuous. Antigua has to be the terminating point as I will be dropping the boat off there. Lots of good advice here thank you, I may do some re routing and have the wife onboard out of Antigua to St. Croix and then the last week take the boat back to Antigua. The guy crew I will have onboard then always enjoy a upwind day or two!