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.