I don't think many Mainers
cruise LI in the summer, seems more the other way round. Many heading South initially follow the coast South to LI Sound ,
day sailing and motoring 60 to 100 miles a day. Most snow birds do some short passages but most of the sail South is usually on the Intercoastal waterway. Some do a few days
passage to the Chesapeake and then mostly the
ICW further South. It is all very
weather dependent and as the other respondent said, can take from 10 days to 2 months.