Matthew,
Definitely some significant distances. I was thinking of Block Island - Greenport on the return leg, then a very full day Greenport - Mt Sinal or Pt Jeff, with an invigorating but well-timed trip thru The Gut.
On the outbound route, I intend to do some meandering. I'm thinking of a side trip up the Connecticut River to spend the night in Selden Cove. Longest continuous trip I've done so far (in this boat) is Oyster Bay-Manhasset, so it should be quite the adventure.
Mike