We're right near you in Northport and actually spent the night in Lloyd Harbor on Sunday/Monday. Didn't see you though!!
We have a 42 foot sailboat and a few places we LOVE to go (like, we HAVE to go each year) are Hamburg Cove (above Essex on the CT. River), Mystic Seaport, Watch Hill, RI (although we can't get in anymore thanks to the shoaling), and Block. Other than that, Newport
is great, Cutty is so fun, Martha's Vineyard
is wonderful, Fisher's is quiet and a nice spot to stop in. Those are our standards each year.
Of the above, Hamburg Cove is one of our favorites. Fresh water
in a quiet cove, GREAT swimming and lovely quiet nights. We can spend a bunch of nights there and not feel like it's too long.
We don't do the South Shore due to our draft
(6'8") but we've gone out to the Vineyard a bunch of times.