2nd Scotts Guide...there is a chart Virgin Islands #12 from 2010 which I have but would recommend Navionics on an IPAD. Cruising Guide publications also puts out a book called Virgin Anchorages which is helpful. There are good weather apps to pu on yoru IPAD or laptop you should have

How are you responsible if you have a captain? Not questioning as much as trying to understand...

As a licensed captain I bear the ultimate and sole responsibility for my (bare)boat. If I am on a boat with a captain I don't get involved as I don't want the inferred liability.

I am now more on the power side now but for your trip I would switch Saba and Anegada as Cooper to Anegada is a long sail and might be uphill depending on time of year. Cooper to North Sound then to Anegada and then back down to Marina Cay/Scrub (get the wife thing) and then JVD. While in North Sound take a land taxi down to Baths and then eat at Coco Maya for the meal and view of your life

I would add Cane Garden Bay and skip 2x at Cooper

The advice I get here is best in class so just keep asking...

all IMHO