I just went out to Block Island from Westbrook and back, sailing that area of eastern LI sound for the first time. I would highly recommend getting an Eldridge tide book which is an invaluable resource in judging the strong currents of the area which can be up to 5 knots. We opted to go through the watch hill point passage on the north side and along fishers island/long sand shoal rather than deal with the Race in a 25 ft boat. Everything went very smoothly.
Of course, being from Old Saybrook, you probably already knew all this. Like your new boat, I am from the Boston's north shore and did not!