That's quite a plan! We did the same thing some (many) years back with Moorings out of Oyster Pond and I think we were almost as ambitious as you at first...

But we started slowing down, if we were in a nice spot it became very easy to change plans and stay another day. We ended up 2 or 3 nights in Anguilla and the rest around SXM, and it was plenty! St Barts can be quite an undertaking...we eventually blew it off and took it easy. You're really going to have fun either way.