To those who have helped thus far - I think we might be settling on the following
NYC drive to Montauk (taking our time), spend the night in Montauk, early ferry to Block Island, and then onwards to Newport, spend the night in Newport, daytime Newport/surrounding area, spend another night in Newport then it becomes interesting, do we:
Drive to Falmouth (2hrs along the coast) and ferry to Martha’s Vineyard (35mins)
Drive to Quonset (30mins) and catch fast ferry to Martha’s Vineyard (30mins)
Drive to Hyannis (2hrs along the coast) and ferry to Nantucket
Spend the night on either island, ferry back and drive to NYC
Are we bonkers?
The drive from Newport to Falmouth or Hyannis is not very interesting. I would vote for the drive to Quonset, which is much shorter and actually a bit more interesting (especially if you take route 1A through Wickford).
Thank you all for your comments about my optimistic travel times
and the rules/regulations regarding minimum stays…back to the drawingboard it is