You have 4 days between Jost and Cane Garden Bay. Why not put those days together? You could probably just spend 3 days in that area - or even 2. If you really want to keep the trip more relaxed, I'd spend 3 days in North Sound. 2 nights at Leverick, rent a car the day you arrive and go out to dinner, explore day 2 and then do dinner at Leverick (jumbies if you can make the visit on a Friday). Then for the 3rd night in north sound, make a short move to Saba or BEYC or any other spot.

It might also help to know - what had your wife in tears?