While I've only sailed past Montserrat and not visited, it is almost straight downwind from Antigua
and if you head
downwind first you might as well visit Nevis
, then Montserrat. But then you'd need to go back upwind to visit Guadeloupe
The Îles des Saintes are wonderful and should be on your list. And the next stop, Dominica
, is my favorite island in the chain and worth not only a visit but a stay.